The 50 Greatest Tennis Sneakers of All Time

The clichéd thing to say here is that Adam "Air Rev" Leaventon has forgotten more about sneakers than you'll ever know, but the truth is—and if you read this whole thing you'll understand—Adam doesn't seem to have forgotten a damn thing. He grew up a sneaker fanatic, paid his collector dues digging in musty basements for forgotten gems, then later parlayed his years of study into a career as an exec at Puma and DC Shoes. Right now he's testing free agency, but that's a good thing for us, as we were able to tap into his seemingly boundless knowledge. Read on and enjoy. —RUSS BENGTSON

TENNIS. JUSTIFIED.

Once upon a Borg, around about 1985, you already had your Bruins, your Shells and your Suedes, and maybe—if you were a fly type of player—your patent leather Concord Mids. If you lived in Philadelphia, New York or Baltimore, maybe you had your Air Force 1s. You tried to have something nobody ever saw before. You tried to customize your joints and put three pairs of laces in them to get that color combination just right and all yours. And at some point you might have said to yourself, “damn, I have laced my joints bar style, zigzag and checkerboard; I have jelly rolled them; and dyed them a shade of burgundy that no other cat has done.” Ultimately, however, they bit your style. How then, my fashionable friend, could you achieve the style they hadn’t obtained yet?

For a very brief period of time around 1985-86, there was an unusual convergence of rap culture and European culture. FILA was an extremely high-end European proposition. Ellesse had a jewel on the back, and you couldn’t afford it. Brands like T.R.O.O.P. and British Knights were about to ride the Euro wave and make paper, and emcees were moving the dial with English accents, both legitimate and make-believe. In that moment, just before Nike put a headlock on the athletic lifestyle market, sidewalks were saturated with Nike, adidas and Puma. But step into your friendly neighborhood sporting goods store, and next to the catgut and Babolat, Kneissl and Prince, you were drawn in by a wall of something very different for your feet. No one could tell you they were skippies either. Euro-pedigreed, and very new to the U.S.. Imported to the store by your favorite retailer. Imported to the block by you.

The list you are about to read details out The 50 Greatest Tennis Sneakers of All Time. The list is necessarily personal and is generally based on the following criteria:

Style: This is criteria number one. It is why I started buying shoes, and why most people reading Complex do also.

Innovation: This is not an article about performance tennis. Still, innovation and forward progress are mission critical for footwear companies. Innovation can come in the form of performance technology, but can also come in the form of advances in fashion or in the manufacturing process.

Story: I am a sucker for a good story. I like the G Vilas, but I really like what Guillermo Vilas was doing during Wimbledon in 1982. I wonder if he was doing it in Puma.

Tennis shoes are dope, I am honored to have the opportunity to dialogue on this topic. Feedback is 100 percent welcome. If you have any, please e-mail me at airrev@mac.com and I'll respond if I can. In the meantime, bust out your Shoe Goo and get to reading!

50. Wilson Pro Staff

Year Released: 1980s

If you ever actually played tennis in the 1980s, then you may have had a coach who claimed to have been a pro [entered one tournament and went out like a sucker]. For whatever reason [coke problem], he never reached his [minimal] potential. But you were lucky to have a coach with that kind of experience [because he always had weed]. If you ever knew a guy like that, chances are he was wearing the Wilson Pro Staff. The Pro Staff was a clean, basic shoe featuring that sexy W logo in the saddle (ladies, back off. . . I just want to play tennis and nothing more). Wearing this shoe enabled you to clearly signal your allegiance to 1977 by virtue of the slap-happy San Diego Padres font reading "PRO STAFF" on the midsole. Somewhere there is an old tennis coach in a Steely Dan cover band wearing these, and hoping for just one groupie. FYI, if you feel like the preceding paragraph accurately sums up your steez, the Pro Staff is still in production today.

49. Kaepa Tennis

Year Released: 1980s

Whenever I mention Kaepa to people (It's not like I go around talking about Kaepa all the time, but still) they think I'm talking about Kappa. I'm not. If you were really trying to come with your own style, Kaepa was one way to do that. Kaepa tennis shoes were weird. The laces tied not only at the top of the shoe, but a second set of laces tied in the middle. Apparently this was based on the founder of the company breaking a shoelace during a match, and having to make a key lacing decision under extreme Sunday tennis pressure. The guy was also a priest at one time, so God probably gave him the high sign during that moment of crisis and self doubt ("tie them shits in the middle, my son, then sell ye them to the public!"). If you look carefully at the eystay of the OG Stefan Edbergs, it is structured similarly. The one kind of dope thing about Kaepas was the removable Kaepa logos. Two triangles. That is typical for cheerleading shoes, but not so much for other shoes. Kaepa still makes volleyball and cheerleading shoes today, so if anyone reading this is a male cheerleader, I can put you onto the Kaepa website, but really you should just stop doing that.

48. New Balance M595

Year Released: 1980s

If you were wondering how big the Reebok Phase One was (coming up later), you only need to look at how bad it got in the heads of Reebok's competitors. Pretty much every brand scrambled to come up with a solution to the butter comfort, nappa leather, EVA wedge midsole and try-on feel of the Phase One. The M595 was New Balance's shot at this piece of business. I don't know if these shoes were actually beige or whether every pair I have ever seen has just been discolored. It wouldn't surprise me if they were beige. Beige leather sneakers, beige computers. People bought beige stuff in the '80s. That would never happen today.

47. adidas Arthur Ashe

Year Released: 1975

This shoe is on this list because it's just an interesting and obscure shoe. I have only seen a couple of fuzzy shots, but somewhere along the line, Arthur Ashe had a signature Adidas shoe based on an inline model called the Matchplay Tournament. The shoe was basically a slightly modified Stan Smith with a vulcanized bottom. In addition to classic white-green, the shoe existed in a white-brick red that almost looked orange. His picture wasn't on the tongue. That would have put it over the top. I don't know how you don't make a bigger deal out of Arthur Ashe if you're Adidas, but I guess maybe he was one endorsement deal too many. Ultimately, Le Coq Sportif scooped him up and the rest is (a very obscure piece of) history.

46. Converse Jimmy Connors

Year Released: 1984

Converse was never really a tennis brand, but in the late 1970's and early 1980's, any major athletic footwear brand that wasn’t in tennis was a mid-major. That's how much tennis mattered. As an original US brand, you really had two choices if you wanted to hire a tennis star. John McEnroe and Jimmy Connors. Chip Hooper, anyone? The Connors Classic released during the 1984 Olympics was awful. Really uninspired. But the original Jimmy Connors All-Star was a really interesting shoe. Very clean, vulcanized bottom and the heel counter featured an extra large Converse star cutout, backed with color (is navy a color or the absence of color?). Jimmy Connors was an animal. He made a major comeback in 1991 at age 39 and reached the semi-finals of the US Open (wearing Air Tech Challenge). To put that in perspective, Bjorn Borg retired at age 26. Andy Roddick just retired at age 30. Of course, Jimmy probably wasn't going home to Brooklyn Decker standing naked in the kitchen wearing heels and making a pot roast.

45. adidas Nastase Super

Year Released: 1978

The original Nasty Nas was a shaggy Romanain guy who did what few others did—got his face on the tongue of an adidas shoe. Now you might say "who cares?" and in 2012 that might be fair to say. Over the years, adidas has become much more generous with its tongue and it is willing to tongue a lot more faces. But at that time, there were very few athletes who received that treatment. So that feature, plus a classic silhouette, gets the shoe on this list. Let's also not forget that Nastase won [who cares how many] tournaments and was ranked [who cares] in the year [I don't care]. What you need to know about Nastase is that he apparently applied the Shoe Goo to over 2,500 women and whenever he played against a South African opponent—this was during the Apartheid era—he greeted his opponent at the net by saying "hello, racist." How dope is that? Nastase was allegedly able to rip referees a new one in six different languages, and he once threw a Nastase Super at a referee for decaring a foot fault. Nasty.

44. Nike Meadow Max

Year Released: 1986

Having spent some time in the industry, I think I know why the Meadow Max was still around in 1986. Sales reps. By 1986, Nike was pushing the envelope hard from a technology standpoint and making issues out of its key tennis assets. Nike Air was widely accepted, and visible air was only a year away. Nonetheless, the Meadow Max-- the official shoe of 8th grade soccer coaches everywhere (after hanging up their Nike Field Generals for the evening)-- was still in stores in 1986. Seems like a situation where a few vocal sales reps had a few vocal accounts that just kept buying back into the shoe. So it kept getting carried over season after season, to the dismay of the product team. I don't know for sure. I wasn't there. I was too busy with my boys clowning the 8th grade soccer coach. The reason the Meadow Max is on this list is that Nike really wasn't always the go-to tennis brand you see now. And before it was, the Meadow Max (and the put-a-paper-bag-over-its-head-and-use-it-till-it's-all-used-up Meadow Max Supreme) was the height of Nike tennis techology. Somewhere in Texas, MVZ is mowing his lawn in these shoes and smiling.

43. Nike Air Zoom Ablaze

Year Released: 1997

If you sort of roll through Agassi signature shoes, you can see Nike initially making minor moves from a technology standpoint, but really just freaking the shoes in a superficial way. Overlays with wacky-ass tie-dye prints, etc. By the mid to late 90's Nike was really doing work with the Agassi range, but it's not clear that anyone really noticed. The Air Assailant from 1998 is a really interesting looking shoe. But when I saw the Air Zoom Ablaze at Paragon, I bugged (then waited for it to be on sale for $39.99). This shoe took tennis technology in an entirely new direction with an anodized exo-skelton for stability that looked like a motherfucking Transformer. I needed this shoe (for $39.99), and I got it (for $39.99).

42. adidas Lendl Pro

Year Released: 1984

I got jumped in 1984. I was in front of an arcade called Zounds on 15th and Chestnut Streets in Philadelphia. I was wearing some crispy new Top Tens. Foam tongues fully erect. New York laces (fat laces. . . we called them New York laces). Exactly enough money in my blue checkerboard OP velcro wallet to see Beat Street at the SamEric theater. Feeling like the mack! Until some bigger kid said "run them shoes!" I can't front. I just handed him my wallet instead. Now, there is no way I could pick this kid out of a lineup now, and I couldn't do it then. But what got stuck in my brainpiece in that split fight or flight (or just handover the damn wallet) nanosecond was duke's shoes. He had white-forest green Shells with two different flavors of green New York laces. That was crazy to me. Totally worth the $2.50 he took off of me. I needed to somehow get my gradient flavor on. I saw Adi color markers for sale ONCE at a store (a Hallmark store), and swore to god if I ever found them again, I'd freak some natural on whites into three shades of blue; then I found Lendl Pros. But I had no money. Damn.

41. Le Coq Sportif Ashe Pro Cup

Year Released: 1970s

Arthur Ashe had a number of brands on his dilznoid over the course of his career. And why not? Equal parts athlete and humanitarian, he was an ideal endorser. After a number of years with Adidas, Ashe signed up with Le Coq Sportif. I'm sure the good people at Le Coq thought the Ashe Pro Cup was a very understated shoe. Very sleek, very European, with triangular perforations on the tongue. And it was. But something funny was going on around the toe box. If your middle toe was four inches long, the Ashe Pro Cup would have fit just right. Le Coq Sportif had a lot more fun reviving the Ashe brand this year, than the company must have had launching it back in the day. Ashe was a little bit of a nerdy looking guy, and his product range could have used a little Noahfication to make it crack. The Ashe Cup is on this list because Arthur Ashe was just a dope name to have on foot. He was an incredible athlete and a civil rights activist. He purposefully brought attention to hereditary heart disease after having a heart attack in his prime, then to the inadequacy of urban health care as he fought AIDS in 1982. In the Oh Twelve, athletes don't really take their time and talent to places like that. They take them to South Beach.

40. Bally of Switzerland The Court

Year Released: 1986

Bally is Swiss brand that had itself a little rap moment around 1984. Bally was part of hip hop culture for some time prior to the launch of Bally sneakers in the US, selling primarily colored suede chukka styles. There were two key Bally sneaker styles that made some noise. The first one was called the Competition (because there weren't already enough shoes in the market called the Competition). That's the one that most people probably know. Doug E. Fresh was wearing them with white floods on the cover of "Oh, My God!" But the Bally sneakers that most people wore were called The Court. The Court had a very pliable, siped gum bottom and came in a variety of suede flavors, notably all-over white suede. To me, The Court looks like it was built more for a squash court than a tennis court. It was the popularity of brands like Bally that led to the emergence of lower pricepoint "street fashion" brands like Travel Fox. I have heard Ballys made around that time hurt to wear.I didn't have much exposure to Bally, and I never wore a pair. Consequently, my corns are a-o-k.

39. Nike All Court Canvas

Year Released: 1975

By 1985, the All Court Canvas was the Yugo of tennis shoes. In 1975, I am sure these shoes meant something among the the Chuck and Pro Keds dudes, but in 1975 I didn't know which one was Ert and which one was Bernie, and the Count scared the shit out of me. By 1985, the average price of a tennis shoe was $35. The All Court Canvas was $15.95. There is no doubt that there was a place for this shoe in the market, but there was no place for it in my closet. Every company had one of these. Adidas had the Nizza; Puma had the Ibiza. Domino's had the basic cheese pizza. The All Court is on this list for two reasons. First off, everyone needs shoes. If all you had in your pocket in 1985 was $15.95, and you chose All Courts over some Fayvas, then that's a good thing. Also, the colorway-- kind of an electric blue on white-- and the tongue logo-- black NIKE logo with orange swoosh, was very iconic. If a psychiatrist showed me those three colors next to each other on Pantone chips and asked me how I felt, I'd tell her I feel like I'm in Beaverton in 1979.

38. adidas Grand Slam

Year Released: 1984

I am a sucker for tricks and treats. In 1984, adidas and Puma were doing all kinds of tricks. adidas had the Micropacer. Puma had the RS-Computer. Adidas introduced the Peg System, and Puma responded with the Natural Vario (which never came out). The Peg system was a big intiative for adidas in 1984. Basically the shoes that incoprated this technology had three holes through the side of the midsole. The product came packaged with pegs in various colors (representing different densities) and a tool to hook it up. The Peg system was in the Grand Slam, Kegler Super and the L.A. Trainer (the jogger that for some reason took over Italy a couple of years ago). It may have been in some other models I'm not remembering. The Grand Slam came in a low and a high. There was a Grand Slam II and then some other successor when adidas established its sport performance branding in the early 1990s. The style itself was very dope even without the pegs. The pegs just added that extra couple of color hits and depth to put the shoe over the top. I don't know who wore it, and I don't care.

37. Nike Air Resistance

Year Released: 1994

If you're Nike, what do you do with Jim Courier? If Barkley is Force and Pippen is Flight, then Agassi is Tech Challenge and Courier is. . . Air Normal? Wait no, Air Dependable? That's not going to get 'em buying these. Let's think about this. He's dependable, because he's so. . . . durable. Yeah that's the ticket. The Nike Air Resistance focused on durability, which probably made sense for a guy like Jim Courier. These shoes got picked up at street level on the strength of the fact that they were completely unbreakable. Possibly the most indestructible sneaker ever created, the Air Resistance had a giant hunk of a sole unit made up of composite "regrind" rubber made from recycling soles of other sneakers. Basically, the Air Resistance chewed up other wimpier shoes and ate them. The most striking feature of the Air Resistance, however, was the huge proprietary Dupont Kevlar overlay on the toe. Version II of the Air Resistance was branded NDESTRUKT and came with a six month blowout guarantee. Now that's old school.

36. adidas Robert Haillet

Year Released: 1964

Ok, listen up young fiends (nerds). The shoe you know as the Stan Smith was originally called the Robert Haillet. The Haillet was the first leather tennis shoe by adidas, and it was only slightly different than the Stan Smith. Signature on the lateral, no picture on the tongue, very, very dope suede heel with no Trefoil and a bug shape reminiscent of 80's shells. Robert Haillet was a French tennis pro who later repped adidas product as a sales rep, because back then you weren't necessarily paid as hell if you were a pro. Haillet's bio on Wikipedia US contains 31 words. Not what you would call a global icon. However, this shoe was so successful for adidas, that after Haillet retired, adidas kept it going with a new athlete, Stan Smith, beginning in 1971. For a minute, the shoe was still called the Haillet, but Stan's mug was on the tongue (with "HAILLET" written above Smith's face, and "STAN SMITH" in italics on the lateral). That was weird and confusing, and it didn't last. The shoe eventually became the Stan Smith in 1978. Now for what it's worth, the whole Haillet-Stan Smith transition is the functional equivalent of the Air Jordan launching in 1985, not changing it until 2003, then calling it the LeBron. That would never, EVER happen today. Oh, and Jordan would be lugging a shoebag around, slinging Roshe Runs. Also very unlikely.

35. Nike Wimbledon GTS

Year Released: 1982

The original Nike Wimbledon didn't really have a lot to do with Wimbledon, other than the fact that John McEnroe wore it at Wimbledon. Pre-1980s, there were-- generally speaking-- five to seven basic upper patterns in the sneaker universe. For example: (i) blucher toe - Nike Blazer, Puma Basket, Adidas Stan Smith, (ii) t-toe - Nike Oregon, PUMA Liga, Adidas Samba, (iii) tab toe - Nike Bruin, Adidas Gazelle, Puma Pele, (iv) box toe - Nike didn't really have one outside of running, Adidas Milano, Puma Dallas (iv) disconnected toe overlay - Nike Killshot, Adidas Top Ten, Puma Trimm-Quick, etc. These basic upper patterns went across most sport categories, along with some outliers for sports whose particular needs resulted in product that may have had to look a little different to accommodate that. The Wimbledon was Nike's basic tennis blucher toe. It changed slightly over the years. The iconic version to me was white with an electric blue swoosh. John McEnroe was wearing this during pretty much any 1970's temper tantrum, but at one point Nike had just about all of their tennis pros wearing this one model. One of the older Wimbledons has been reissued a few times recently, slightly reinterpreted, as the Tennis Classic. Later versions were completely different and incorporated the McEnroe checkerboard, signature Wimbledon purple-green and sometimes incorporated the Wimbledon logo.

34. Nike Air Tech Challenge 3/4

Year Released: 1989

Innovation for a brand, for an athlete, for an initiative is mission critical. However tempting, innovation is not acheived merely by cooking up a Miami-colored shoe that "scares your opponent across the parking lot." Innovation, marketing and trend design all need to be aligned and cannot come at the expense of one another. Additionally, when brands consider their roster of Athletes, it's important that each bring a unique quality that permits the brand to justify the creation of product that hits a certain market-facing need. If every asset doesn't have a reason for being, then you are creating redundancies. For example, Nike used Barkley to address the late 80's-early-90's trend of big, chunky, Air-based shoes with the Force range and used Pippen to go after guards and small forwards with shoes whose design spoke fluidity and forward motion. Andre Agassi represented the ability for Nike to progress the Nike brand forward in tennis. As the 90's began, bold color was everywhere. Fashion was irreverent. Nike needed to play there, and find business and technology justifications to get after irreverent design. As a lot of the one-hit brands of the 80's fell off and the usual suspects remained quite conservative, Nike took the Agassi range in a very aggressive direction that we now view as synonymous with the early 1990s. Additionally, Nike initially linked the instances of bold color on the Air Tech Challenge to the presence of Durathane on the shoe, a material technology that increased upper durability, particulary in the toe area. Trend justification: check; business justification: check; athlete justification: check; performance technology justification: check. Irreverance officially justified.

33. Lotto

Year Released: 1986

Lotto is a Northern Italian company that at one time sponsored Boris Becker and Martina Navratilova among others. From their vantage point in Northen Italy, during what was a major growth period for the Company in their technical sport business, I wonder if they even knew that kids were wearing Lottos on the block in the US. I didn't know shit about Lotto. I don't know what this pair was called, and I also don't know what sport is was meant for. Based on the strange asymmetrical toe overlay and gum bottom, it looks more like an indoor shoe than a tennis shoe. Volleyball? Table Tennis? Handball? All I knew for sure was that Lottos had what we called "a removable Lotto." I didn't know the Lotto logo was called the "double diamond," but I did know that kids were running around with shape shifting shoes that could match up with any gear. How fresh is that? That's what you call having a moment in the sun. Blahzay Blahzay had one of those. They usually do not last.

32. Yamaha Asahi PM-L Leather

Year Released: 1980s

Woooo. Now this was a case of international mystery. Intrigue. What in the world were these? Where did they come from? Asahi Shoes were made by the Yamaha company out of Japan. As far as I am aware (and I only know what I remember here), there were two styles of the Asahi. One was basically a leather Campus, and the other was a leather Bruin. They had two stripes instead of three. I am pretty sure they were both on vulcanized or cold cement bottoms. But the dope thing for me was the disco break! Asahis had a crazy heel overlay. Wide, curvy, with a big yellow dollop in the middle of a bigger orange one, backed with navy. Looking very Verner Panton 1972. These were crazy distinctive, and no one had them. I never bought them because they were always sitting right next to Lendls or some other shoe I wanted just a little bit more. If Asahi relaunched right now, it would work as-is, no tweaks.

31. New Balance CT550

Year Released: 1984

I caught onto New Balance kind of all of a sudden. I guess there wasn't a whole lot of distribution where I lived outside of running models, which I wasn't really checking for until maybe 1987. Then all of a sudden, New Balance court product started to pop up on the street. In retrospect, these were very conservative shoes, and I don't really do white on white. During this period, New Balance really was "endorsed by no one." This was before the Worthys, and there was no hook, no gimmicks and practically no color. But in 1985, New Balance was not Nike, Adidas or Puma, so it was something different. The New Balance CT550 was a tank. There was a mid as well called the P540 that I owned, but I think that may have been a basketball shoe. I bought them at Pearson's Sporting Goods (which also sold Viewmaster reels and had crazy Star Wars toys). These were great shoes. The reason they are on this list is because I wasn't trying to blow through shoes each week. If you came up on New Balance court shoes from the 1980's this week, you could put them on and wear them right now. At some point, someone told me what the letters stood for (CT550, P540, etc.), but I don't remember. New Balance generally went up to size 17EE, but if you wear a size 17 and your feet are wider than they are long, you are probably not playing tennis.

30. Puma Match

Year Released: 1970s

The Match was basically PUMA's version of the Stan Smith or Nike Wimbledon. Clean, generally white-based, blucher toe, perfed logo. Every brand had one, and each was important to that brand's business. The Puma Match fell into this category. I really never saw the shoe until 2004, thumbing through old catalogues. The Match is even slimmer than the Stan Smith. Kind of a grown-ass man shoe. There were about ten shoes that Puma called the Match at various times. The best one has slim suede overlays on the medial and lateral forefoot. For protection, but also it's just a cool design feature. The Match is a very slept on-shoe. If you ever see them in person, they are worth a try-on.

29. Ellesse Tanker

Year Released: 1980s

The Ellesse Tanker is really cheating. It probably wasn't a tennis shoe. It was more of a street shoe. The Tanker had a giant "stepped on" Ellesse logo on the quarter, which was a pretty progressive branding play at the time. It came out around the time a number of other brands were doing the all over thing (Lotto country flags, for example). The most interesting thing about this shoe is that it might have been the first artist co-lab in the history of footwear. Ellesse got down with an Austrian designer named Marc Sadler, who had done a bunch of industrial sport design, including ski boots and moto equipment. The Tanker was part of a collection called "Tank Attack," which included a few other silhouettes as well. Let's see if Russ and staff can even find a picture of these, so I don't need to start digging in my boxes. @DJ Emz, these should be in your closet. You can have my pair (when I die).

28. Nike Impulse

Year Released: 1982

The Nike Impulse was a very dope shoe with a very unique profile. It also had metallic silver underlays if I am remembering it correctly. Which doesn't mean anything, but it's just a weird and interesting materials decision, especially when you combine it with natural nubuk overlays. The shoe was a three quarters, and was basically a Mac Attack before the Mac Attack, on a PU midsole. Whenever I saw this shoe on feet, the PU midsole had always already turned to margarine. I am going to take another guess at what happened here. If I'm wrong, that's ok and maybe it will even get someone involved with the Mac Attack to snap back (more information is always better). I am guessing that the product team worked with the athlete and offered him an array of general silhouette types as the starting point for his signature model. I have to imagine that when the Mac Attack design conversation happened between John McEnroe and the Nike footwear team, the Impulse was one of the shoes on the table during that conversation.

27. adidas Forest Hills

Year Released: 1979

Complex is WORLDWIDE like Akinyele, so some of the shoes on this list may mean more to folks in other regions than they do to me. Or they might mean something different. The Forest Hills is legend in the UK. In the US, it's only for the fiends. There were many versions of the Forest Hills, and frankly, during a time when both Adidas and PUMA routinely named shoes after the location of key athletic events, it was fly that Adidas was checking for Queens. The Forest Hills I know came to be in 1979 and was reissued in 2002, at a time when Adidas didn't really seem to know what to reissue next (which resulted in some really interesting re-issues. . . Vina del Mar. . . huh?). The shoe weighed in at only 8.8 ounces (250 grams for my football brothers), and was re-issued right out the gate in white-metallic gold with a taxi yellow cupsole. That's brave right there. The sole unit color blocking is very similar to the lightweight product you see killing it in 2012. This all happened in an era before light equalled value. Sometimes Adidas is sneaky ahead of its time.

26. Reebok ACT 600

Year Released: 1985

The one thing that the Reebok Phase One (coming up) was not, was, um. . . particularly cool. If it hadn't been so new, so incredibly plush and so different from other product out there, it would have been a skip. A high school science teacher shoe. If you don’t know what that is, try to remember what that nerdleman was wearing when you were in 9th grade. The Act 600 took the next step. Similarly plush, the Act 600 had just enough color to set it off in the summertime, but remained refined enough to facilitate your request for Grey Poupon from the Rolls Royce in the neighbouring lane (see what I did right there?). Since I really had no point of reference for Reebok other than Phase One, I thought these were actually called Phase Twos for a very long time.

25. adidas Stefan Edberg

Year Released: 1986

I loved the Edbergs because I love green-yellow shoes. I wish I had something a little more cool than that, but I don't. I have no idea why I liked green and yellow shoes. I think it's the duck sauce-mustard syndrome again. Back then (and even now), there are certain colorways you see all the time. Green and yellow has never been one of them, so I guess to me these were a way to flavor something other cats would be unlikely to wear. Other green-yellow shoes I have loved along the way were the Spotbilt X-Press and the New Balance 491, which popped in a lot of different colorways, green-yellow among them. When Nike owned Savier and did a kindasorta Air Trainer in green-yellow, I almost bought it just because of the color. In 1986, I wanted Lendls (coming up) in green-yellow, so I bought Edbergs. Stefan Edberg wore Lendls before he had a signature shoe. I am guessing that when he got his own shoe, he wanted something that looked like Lendls. So Adidas gave him something that looked like Lendls. Except they were green and yellow (Hopefully someone at Adidas, said "hey man, is anyone else concerned that these look too much like Lendls?"). The overall Edberg package was kinda eh. I just threw away an old Edberg track jacket. It was made of crinkle nylon and made me feel like Jerry Stiller visiting Del Boca Vista Retirement Community.

24. Nike Air Tech Challenge IV 3/4

Year Released: 1992

The Air Tech Challenge IV was the last Agassi shoe on acid and most people just call it the Agassi. Following on the heels of fluorescents and hot lavas, the Air Tech Challenge IV incorporated a tie-dye style print that showed up not only on the uppers, but was also echoed on the midsoles. After this shoe, Nike really switched gears in the Agassi collection and focused less on whyling out and more on tennis. Agassi also went bald (or un-touped. . . still not clear to me). Point is he started to look a lot more like Bob Newhart than Tommy Lee, and his shoes got a lot more businesslike too.

23. K-Swiss Classic

Year Released: 1966

Listen up, money. Or should I say honey. K-Swiss blew the fuck up in 1984. I don't even know if they made more than one shoe, and I don't even know what that one shoe was called. It's called the Classic now, but it probably wasn't then. It was the K-Swiss to me. The K-Swiss was very clean, but it had a couple of really interesting features. Five stripes, obviously, and it also had D-rings. The most interesting feature was the toedown. It looked like a sixth stripe, but it was really an underlay, which is unusual. I think that this shoe was received differently depending on region. In Philly, the K-Swiss was a girl shoe. I knew a grip of girls who wore these with some baggy E.G . Smith socks and the white-royal Bennetton rugby. That was a status uniform in 1984. The socks alone were $10-12, which is like $22 today. In New York, somehow this was a guy shoe too. I almost fell for a patent leather version one time, but I came to my senses. If I came up on an old pair of the patents tomorrow though, I would wear them.

22. Nike Air Challenge Huarache

Year Released: 1991

Huarache was a huge (and risky) initiative for Nike in 1991. Huarache technology was based on a very strappy Mexican leather sandal style that dates back even further than Clark Kent. So that's a really long time ago. All Huarache product featured "Huarache Fit" which was basically an inner-booty made of neoprene and spandex that held your shit in just right. The campaign slogan was "Have you Hugged your Foot Today?" and a lot of Nike Athletes were wearing them off court, just because they were so comfortable. That technology benefit also yielded a distinct and dope visual that emphasized the upper over the sole unit (unlike Nike Air). Neoprene and spandex take bright color really well, and the huarache-style straps that accompanied them along with the space age Huarache logo, gave Huarache product a hypertechnical look that Nike then circulated across footwear in many of its sport categories, including Running (Air Hurache), Basketball (Air Flight Huarache. . . the Fab Five shits) and even Tennis. Personally, I was down to squeeze my shit into a good-looking booty, so I liked Huarache a lot. The Air Challenge Huarache was Nike's effort to cross-pollenate the Huarache iniative with Tennis product, and if you are going to take a chance on some wild shit, you do it with Andre Agassi. To me, these looked like half-Jordan VII, Half Tech Challenge and Half Air-Resistance, so that's at least 150% good.

21. Nike Challenge Court

Year Released: 1983

When, you were a kid in 1982, didn't really have a lot of leverage. Either you were lucky, and your mom brought home some Bruins or Gazelles, or you were my homeboy Mal, and your mom came home with some Winners from Sears. Challenge Courts were the first shoes I ever picked out myself. I don't even know whether they are really tennis shoes, because they probably have basketball functionality too and, in fact, the Sky Force 3/4 from 1983 is pretty much the same damn shoe in leather. I do know that John McEnroe wore these after the Wimbledon and before the Mac Attack. I bought these because every Nike shoe I had had up to that point (Cortez, Bruin) had a tab toe overlay. At the time, cats were beginning to lace their shoes wider, and I didn't really know how to achieve that look. I was a big kid, and I didn't want my shits looking dainty. The big mesh vamp with the round overlay made Challenge Courts look bigger and wider, which I liked. At the time, I thought that this toedown was something reallly revolutionary, but Adidas and other European brands had been making shoes with this general outlook forever. Herman's Sporting Goods had these in two colors. White-red-navy and white-burgundy-gum. Burgundy was my shit at the time, but burgundy was everyone's shit in 1983, so that color was sold out.

20. Gucci Tennis

Year Released: 1984

I used to actually play tennis in these, but they blew out fast. So I was getting a new pair almost weekly. Yes. That's how it happened. Schooly D, Rakim and I would go to the store and buy some. We would drink champagne on the way. I would ghostwrite most of their rhymes. Don't tell anyone. Then we would pick Dapper Dan up, and play doubles at Flushing Meadows. Yessir, that's my story. The Gucci Tennis doesn't really need any introduction. Maybe some clarification for anyone who felt good about buying S. Carters, and maybe now thinks Gucci is ripping off Reebok. The Gucci Tennis seems like it was the perfect reaction to the convergence of hip hop fashion, euro sport fashion and chunky tennis shoes like the G Vilas, Lendl Supreme, Rod Laver, etc. Whatever prompted Gucci to do this, they nailed it and inspired straight up material lust-- need. This was a stick-up kid shoe. These shoes were so far from accessible that they made no sense to even consider, unless you were making obscene money and were willing to spend it on one pair of shoes. I saw them once. In the window at a store called Boyds, which was a frequent Joey "Skinny Joey" Merlino stop. Stylistically, the shoe was spot on. From the material mix, to the logo hit on the tongue, it's no wonder Reebok "paid tribute" with the S. Carter. An interesting aspect of the shoe was the laces. They were round laces that looked almost trail inspired. Some day, I would like to understand the process behind this shoe and how it came to be.

19. Reebok Court Victory

Year Released: 1989

Ok, I don't have any good reason to knock these at Number 19. Reebok made a power move with the Pump initiative, and went right after Nike, and if you can't appreciate that, you are Cowboys-Lakers-Yankees fan (all three at the same time, a/k/a a soulless front runner. . .). Also, you can tell that a lot of thought went into the technology that 95% of wearers weren't going to care about (Coolmax lining, Hexalite, protective rubber toe at Michael Chang's suggestion ("thanks Mike, great suggestion!... [can someone get this nerd the fuck out of the conference room?]")). But also the tricknology that 95% of the wearers apparently did care about and still do today. The Pump. So, yes, I get it, and yes objectively I can appreciate it. And I do like the Instapump Fury, so I'm not anti-pump or anything. I just. It's just. Eh. Next shoe.

18. Puma Boris Becker Ace

Year Released: 1986

Raise your hand if you are 17. Now keep it raised if you have won Wimbledon. Didn't think so. Go home and consider where it all went wrong. Consider dropping out of school. Definitely stop wasting your parents money on sneakers. Boris Becker won Wimbledon when he was unseeded and 17, a year after going pro. He wore Ellesse from the socks up and Puma footwear. In 1986, Puma came with a butter soft nappa leather shoe (Reebok was doing it, so a lot of other brands started to do it too) called the Becker Ace. I first saw this shoe on the wall at Everyone's Racquet in Center City Philadelphia. Phase Ones had been copped the spring prior. To me, the Becker had everything the Phase One had, including the cushy terry lining, but with a blue Boris Becker signature that looked metallic when the light hit it right and some added detail and color. These were an immediate purchase for me. I have two pairs on ice right now. What am I doing not wearing these?

17. Tretorn Nylite

Year Released: 1965

Tretorn was a Swedish company whose primary business was rubber footwear. Tretorn means three towers, and represents the three exhaust towers sticking out of the original Tretorn factory in Helsingborg, Sweden. Tretorn had more than just a moment in the early to Mid 1980's. For about five years, you would see this shoe twenty times a day. Like K-Swiss, who wore the shoe depended on where you lived. Bjorn Borg wore these in the US in the US when his contract did not permit him to wear Diadora in the US or Canada. More importantly the middle school murderer's row of Rebecca, Aurli and Liza all wore these when I was in sixth grade. Those were some formative times and those were some fully-formed females. Because of this, it's hard for me to think of this shoe as anything but a girl shoe, but that's really not the case. I have seen at least one grown man cry over a pair of Nylites. During the early 2000s, Tretorn was acquired by Puma, and repackaged as a more grown up trend brand. Tretorn's brand and product is extremely well-thought out and well-designed. If you have never taken the time to see what Tretorn cooks up each year, you should. I have seen people lose their minds over certain Nylite colorways, and the utility boots are very dope.

16. Diadora Borg Elite

Year Released: 1981

If you want a quick snapshot understanding of how important tennis used to be, look no further than the lifestyle impact of the game and the athletes. If you were to ask a lot of people what the late 1970's "looked" like, then flashed a picture of Bjorn Borg, they would probably say "yeah, that." Borg's overall "look" caught-on in a primordially Bieberish way. There were as many Borg's walking around, as there were Freeway's walking around Philly in 2006. Mostly, Borg was known for his apparel. If you flip around the interwebs a little bit, you are likely to see some of most incredible Fila gear ever produced, as well as Borg's own Fila range featuring his signature "BJ" logo. If you want to take it a step further and really feel the power of Bjorn Borg during this era, part your shit in the middle and wear a very tight headband. There, feel that? The Borg Elite was probably the premier tennis shoe of the very early 1980s. Diadora produced a handful of colorways, but the Gold Elite was different. It was made of supple kangaroo. It also came in a nylon drawstring bag with Borg's portrait on the side, had a numbered certificate, and had a very dope metallic gold logo (I think they called the logo the flash in the UK. . . this shoe probably meant more in the UK than anywhere else, where it was picked up by casuals in multiples). Once in a while the shoe gets re-issued, but since Borg no longer collects Diadora checks, the signature is missing and they are called the B. Elite. Whatever you say, b. Interestingly, Borg's contract with Diadora did not allow him to wear Diadora footwear on court in the US and Canada, so he wore Tretorn in those countries.

15. Ellesse Mesh Tennis

Year Released: 1980s

In 1985, Ellesse and Fila were THE lux brands in the sneaker world. You could argue Bally, or Gucci, but they were really luxury brands that decided to bang out some sneakers, whereas Ellesse and Fila were actually performance brands that were just so damn expensive, that they became a luxury. I know that most heads, if they remember any Ellesse shoes, maybe remember the Mo Cheeks joints. For me, Ellesse will always be a tennis shoe. Ellesse had some great athletes-- Boris Becker, Guillermo Vilas-- but mostly just in the apparel. That said, Ellesse sneakers had me open at this time. The key shoe for me was nylon and overlay heavy, and I don't even remember her name. And if I'm being honest, she looked better from behind. The molded Ellesse logo on the back-- a half tennis ball plus a pair of ski trips to symbolize the companies presence in both sports-- combined with a greyish cream molded heel counter that looked very much like the heel of the Air Pressure, was incredibly official to me. I only owned one pair of Ellesse back then. I own a few now. If they still made them like that, I would buy them all day long.

14. Diadora Maverick

Year Released: 1986

Unlike Ellesse, Fila, Tacchini, etc., Diadora was known for its shoes more than any gear it produced. Diadora made a lot of dope shoes in the 1980's. I was extremely depressed when I saw re-issues in giant piles in bins at the Colosseum Mall in 2006. The Diadora shoe that heads probably remember most (but probably never saw a pair in person) is the Borg Elite. But the shoe that really got me open to Diadora was the Maverick, and here's why. I had seen nubuk here and there before the Maverick, but in the summer of 1987, Diadora freaked the Maverick an crayolafied array of nubuk colorways. I am sure I saw at least five, but the ones that stick in the crane are a very serious black-silver, and the babiest and bluest of baby blue, that just shut it down in Philly that summer. In fact, now baby blue is a totally acceptable sneaker colorway, but in 1987 it was pretty unusual. Maybe even a little bit feminine. But now that Diadora was doing it, it was like my man June of Bestown, France: it wasn't feminine-- it was just European. I think that by 1987, European brands were ready for prime time in the urban market, and I can recall Philly Sport, Shenk Bros. and City Blue selling these at a price that was reasonable enough that it worked. Also, no matter what the colorway was, each had the Italy colors on the heel tab. Doing something like that might work in the fashion market for brands like Christian Louboutin. But in a market where kids are trying to match, that is a bold ass move. But it worked. I have a very soft spot for this brand, and I wish them success.

13. Nike Air Tech Challenge II 3/4

Year Released: 1990

Wimbledon doesn't do advertising in the stadium. Royals attend. Spectators eat strawberries and cream. It probably isn't ok to wear hot pink neoprene, acidwash and have crazy hairspray hair(pieces). But if you're really good at what you do, you can get away with a lot of things others can't. Andre Agassi could get away with this sort of thing. And on the block, where wearing hot pink probably wasn't really ok for guys in 1991, you had Nike incorporating fluo pink into a lot of its key models. Again, if you're really good at what you do, you can get away with a lot of things others can't. The Air Tech Challenge II saw Nike grow more confident in the Agassi design direction. Featuring full-length Air, visible this time in the heel, the shoe also flossed "hot lava" gradient overlays for added buckwhylin'. The tooling from the Air Tech Challenge II was de facto ahead of its time. It must have been, because Nike dragged it out again this year and popped the Kanye's on top. Or maybe that just makes the Kanye's late. Don't matter, because eager beavertons slept on sidewalks for the Tech Challenge redo and the Kanye too. Did I mention that if you're really good at what you do, you can get away with a lot of things others can't? Not sure if anyone noticed the white-royal blue-infrared colorway. Completely different "hot lava" print and was intended to be the McEnroe colorway of the Air Tech Challenge II 3/4 for Fall 1990.

12. Reebok Phase One

Year Released: 1985

Gigantor shoutout to Everyone's Racquet at 17th and Chestnut in Philly. The store still exists, but in a different location. The poor gentlemen who owned this store were cursed with a crew of 14 year-old fucklenuts loitering on the try-on bench for up to three hours a day. Rapping. Making fart noises (both real and manufactured). Tripping paying customers, probably costing Everyone's Racquet sales on the daily. Dumming out on new, weird European tennis shoe brands on the wall. They stuck with us though, and some of us made a career out of it. That is where I first saw the tasty, supple, nubile Phase One. After years of NikeAdidasNikeAdidasNikeAdidas, touching the Phase One was like getting some strange. Reebok was an English brand that began to be distributed in the US in 1979, but the Phase One in 1985 is the shoe that made me look twice. I think I first picked it up because it looked more like a running shoe than a tennis shoe. There was a cardboard sign in the store that said something like "the only leather shoe that you don't have to break in." And it was 100% true. As soon as I held it, I was locked in. The upper was sort of a creamy off-white garment leather. There was also a nylon, but fuck the nylon version. I remember the smell. To this day, I have never had a shoe that felt as comfortable when you first put it on. On the flip side, the price you paid for all that buttercream comfort was that they blew out in a week. If only there were a spectacular head of lifestyle development at Reebok from an historically-significant shoe manufacturing family in England who could bring that feeling back.

11. Nike Vapor 9 Tour

Year Released: 2012

You may have noticed that this list is not heavy on recent or current product, and that's fair. As always, more information is better, so please feel free to respond with recent product that deserves to make the cut. Generally, though I'm not seeing it. Time marches on, and there is no doubt that tennis footwear technology has advanced exponentially from the 1980s and 1990s. For the most part, however, styling has not. I recently had the opportunity to parlay with a long-time tennis retailer I trust, I asked him what's happening now. He pointed to a plasticine horror show branded Babolat. Damn. I thought they only made griptape. While I have no reason to doubt the technical proficiency of the model he showed me, I'd rather wrap some griptape around my feet (and my neck) and hope for the best. This is definitely NOT the case for Nike's Vapor 9 Tour, Roger Federer's current shoe. The Vapor 9 Tour screams "technical," whispers "light" and then lets you be the judge. There are familiar cues all over the shoe, Air Huarache-style toe overlay (tributed most recently by the Supra Owen), Zoom cushioning branding and what jumped out at me the most-- a cage recalling the 1996 Air Max Tailwind. The cage is positioned as a fit system that uses "fingers" to custom mold the shoe to the wearer's feet. As the foot moves during play, the fit adapts. While the technology is new, the concept is not. The Diadora Borg Elite claimed to have a lacing system that "self-adjusts while you play." Still, this is a very fresh looking shoe, with serious street potential. Wonder who designed them?

10. Fila T-1 Leather

Year Released: 1984

Let's just get this out of the way. FILA was an incredibly powerful sport luxury brand. Retailer ads in the back of tennis magazines listed prices for various shoes. But almost always, next to FILA, it just said "CALL FOR PRICE." FILA was so synonymous with high-end that everyone wanted a piece. Rap groups named themselves after FILA. Ford tried to go high end and collaborate with FILA on a Thunderbird before collaborations really even existed (white leather seats anyone?). So if you don't know, now you know. And if you still don't know, you better axe somebody. Detroit desperation aside, FILA was an apparel powerhouse in tennis and skiing. FILA tracksuits were rich—regal even—and barely attainable. I remember finally being able to get my hands on some FILA at the pro shop at Pier 30 in Philly and walking out with a plastic visor, because it's all I could afford. For me, FILA really had one tennis shoe that mattered: the T-1. The T-1 is a prime example of sleek European design, and how brands like this became a way for you to set yourself apart from your homeboys in 1985. I know FILA apparel tried to make moves like eight years ago. I have the orange wool track jacket to prove it (and it's crazy). I should have bought the kelly green one when I saw it too. More recently Premium Goods busted an amazing looking and completely slept-on T-1. So did Classic Kicks. FILA has a big footwear business in 2012, but it's obviously aimed a lot differently. When I see things like the Premium Goods T-1, I can't help thinking how much I'd like to get my mitts on that brand. Hey Jon Epstein, can we get a drink?

9. Puma G Vilas

Year Released: 1983

Over a storied 64 year period, the other Dassler brother has hitched its fortunes to a crazy array of historically significant athletes: Jesse Owens, Pele, Jay Piccola, Tommy Smith, Diego Maradona, Clyde Frazier and now Usain Bolt. Whether by design or by chance, most of these icons are as famous for what they stood for off the court as on it. Guillermo Vilas was no exception. Off the court, Vilas stood for suntan lotion and royal tail. In 1982, he straight up skipped Wimbledon to do the damn thing with Princess Caroline of Monaco on an "undisclosed island" (Maui) for a week. My man Guillermo. The G Vilas launched in 1983. It was a tank on a giant PU bottom. Here is why the G Vilas matters. Of the 50 shoes on this list, there are three that have been commercially successful from launch to right this minute. The G Vilas (now called the GV Special) is one of them. In some areas of Philly people call them Luttermans. In other areas, people call them Sweetings. I was at the DMV in Philly for six hours last week, and I must have seen 25 pairs on feet.

8. Le Coq Sportif Noah Star

Year Released: 1985

I never planned to wear a big Coq on my foot. It sort of just happened. I don't think that any brand has ever come so completely on point so completely out of left field, and done it so naturally, as Le Coq Sportif did in the mid-1980's. Le Coq's history is grounded in cycling, football and tennis, and I think the cycling piece is what was behind the brand's isolated explosion during that period. There was a moment in time when flashy prints and European sport fashion converged, and I think that Le Coq's liberal use of color and wild color blocking in its cycling business influenced its other sport categories. Being from Philly, we felt a little bit invested in the success of Jazzy Jeff and the Fresh Prince. That also meant that we felt like the TV show was a watered-down caricature of the culture. The Street Beat and WDAS versions versions of that crew meant a lot more to me. Still, you can't really deny that Will Smith was a huge influence on fashion trends during that show's run. And that dude really enjoyed him some Coq, cycling hats included.

The other piece was Yannick Noah. Noah was a really unusual tennis player. He would routinely chase down balls and go through the legs to save (or win) the point. He was also a really alt looking dude. Dreadlocked, gap toothed, mixed heritage. When we had to pick French names in eighth grade French class, I went with Yannick. Fortunately, it did not stick. The logo Le Coq designed for Noah was a mcnugget of blocked color, and somehow it just worked on all of his apparel and footwear, regardless of whether it actually matched. The Noah Star was the key shoe for me. Very clean shoe, great shape, plus huge TPU heel stabilizer with a tasty molded Le Coq Sportif Logo. Le Coq called the heel stabilizer "Le Heel-Stabilizer." Leave it to the French guys to come up with clever stuff. I never owned a pair of these, but I did own the 1987 Noah Comp in white-red-grey, which had the dope Noah logo on the tongue. These are great shoes, and Le Coq Sportif is a great brand with all kinds of iconic product. Over the years, I have heard whispers regarding a shoe called the Dominator that looks like a Noah Star or Comp, but in mesh mid. If that really existed, how in the world did it never make it to the U.S.?

7. adidas Rod Laver

Year Released: 1970

Here's the thing about the Rod Laver. This is a grown man's shoe. For whatever reason, adidas made the design decision to go superclean. Full-on mesh and no stripes at all. That goes for both the original 1970 version, as well as the version that still sells commercially in 2012 (pictured here). in 1986, that was a big strike against the shoe. I needed those stripes. Time keeps on slipping, however, and in retrospect I get it. If adidas had put stripes on this shoe, it would have been the Nastase Super. The other strike was the PU midsole. Built for comfort, PU was a positive technology benefit. But when fluorescent light hits it, or when it's old, forget it. Here's the thing. Back in the day (before Biz began), people didn't have 10, 20, 80 pairs of sneakers. They had one. Maybe two. The Laver was a grown man's shoe too. So whenever I saw it, it was on an older person. Because that person didn't tear up his shoes like a teenager would have, he would break them out summer after summer. So everytime I saw the Laver, all I saw was pee pee yellow midsoles. It wasn't until the mid-1990's that I really came to appreciate the clean, breathable simplicity of the Rod Laver. I was also really feeling the work Oki-Ni did with the shoe in 2004. Wolf fish skin? Like Colombian fish scale, ask my man Ishmael!

6. adidas Lendl Supreme

Year Released: 1984

Frick whatever the frack you heard about the Air Jordan III any Jordan being the first $100 shoe. The Lendl Supreme and Forum were the first $100 shoes. Period. The Lendl Supreme was not a shoe that was attainable for me or anyone I knew. But goddamn did I fiend for it. I always sort of just assumed that Ivan Drago was based on Ivan Lendl. A very effective, but very boring and predictable machine. Maybe that's why adidas had to do work on the Lendl collection over the years. This shoe was the opposite of Ivan Lendl. Full of tricks and treats, molded pieces, overlays, the whole nine. The shoe changed over time to incorporate the cat logo, when that became part of the apparel collection. adidas also took almost the exact same upper, popped it on the Rod Laver tooling and called it the Lendl Champ.

5. Nike Air Ace

Year Released: 1988

The 1988 Air Ace is more slept on than Krown Rulers, Low Profile and Tempurpedic combined. I never owned these in 1988, and in fact I only saw them once in a store. These were technical tennis shoes, and I don't think they made it much beyond pro shops and sporting goods stores. So if you missed these, it's because they weren't there (or because you weren't there. . . you are 20, and this was 1988). So to me, Air Ace 88, for a long time, was part of a personal mythology: "no, b, I swear to god I saw some lowtop Revolutions in this one store." Until one fine day way after the fact when I got my hands on a pair, at a store called [I ain't telling] in [I ain't telling], New Jersey. I think the key to this shoe for me is the the shape, which is practically perfect, and the inner structure of the shoe. Nike called it a "Footframe" with a "Dynamic Fit Sleeve." Actually, no. The key to this shoe for me was that I couldn't have it. That was also the key thing about my girl, but then I got her, and I still like her. So maybe it was the shape. Anyhow, there was also a 3/4 planned for Fall 1988. One colorway only—white-capri blue-yellow. I have never seen it in person, and I think it got dropped before it ever hit the market. The Air Ace was dead in six months, by the way. *Please, my man, don't confuse this with the 1983 Air Ace, which was reissued in more colors than we ever needed in 2000 to take out the PUMA GV Special, which it did.

4. adidas Stan Smith

Year Released: 1971

The Stan Smith is the KRS of tennis shoes. It has existed—consistently and successfully—in its pure form for 47 years. There are a not a lot of shoes that can claim that (Chuck Taylor, Jack Purcell, Keds Champion, any others?). So I don't think there is any debate that this is in the pantheon of the greatest tennis shoes ever. But this is a personal list. In 1986, the Stan Smith was more widespread than Challenger. Yes, it got burn on the block. It also got burn with your mom and dad on weekends. And your mom and dad's mom and dad at the senior citizen tennis classics. And with all of the girls in the schoolyard. For a fiend like me, this shoe was just too widely available. Too many girls wore it. It was too elegant, too streamlined and too clean. Years later, as a grown-ass man, I began to mentally connect the perfs, understand its simple elegance and appreciate it almost as more of a dress shoe than a tennis shoe. I think what got me open was a very similar all black shoe with hard aniline leather called the Official, as well as an all-over green and all-over red pair that King Emz made me aware of. I would have worn those. In fact, when I got my mitts on the PUMA Match in 2005—I can't front—I had those on the brain. At the end of the day, this general upper pattern has appeared on hundreds of tennis shoes. No model has pulled it off as gracefully as the Stan Smith.

3. adidas Lendl Competition II

Year Released: 1984

Propers to the brilliant product team at adidas for getting as much burn as it did out of Ivan Lendl. How boring was Ivan Lendl? Here's the best the adidas marketing team was able to come up with: "When your name's Ivan, you can't afford to look terrible." Yikes. ("Heyyyy. . . what if we freak a reference to a Russian dictator from the 1500's who conquered not only Astrakhan, but also the Khanates of Kazan? That'll get 'em buying adidas!"). Nonetheless, over about an eight-year period, adidas destroyed it season after season, not only in Lendl Footwear, but also in Apparel. Early Lendl gear was extra-crispy argyle that was completely innovative and different in the athletic world. From there, it morphed into a study in geometry, then a wild cat face design that in the 012, you would be more likely to see from Alexander McQueen than you would any athletic brand (although I guess Jeremy Scott, but you might get a shoe with a real live cat on top. . . tough to pull off). adidas even teamed up with an Austrian company called Kneissl on the flyest Lendl racket ever. Put it this way: if Ivan Lendl ever brought women home on tour, it was only because of the adidas product team.

On the footwear side, I can remember no less than nine very good Lendl shoes. And a couple of real strugglers that popped out of the machine at the end of Lendl's run (I see you, Lendl Favorite!). For me, the best of all of these shoes was the Lendl Competition aka the Lendl Comp. For the initial launch, the Lendl Comp was white-blue, but the second time around it matched the white-red-blue colorway of the Lendl Supreme. When Lendl apparel came up with the cat motif, it showed up on the tongue of the next Lendl Comp (my man Digital Milo owns these. . . he'd get robbed if he didn't have such dainty little feet). The reason these were so fresh was that they pretty much did the same thing for your feet as the Lendl Supreme, but they were mesh, looked lighter and better for summer run, and they weren't $100. When Adidas relaunched these a few years back, I bought like three pairs—when they went on sale (for $29.99).

2. Nike Mac Attack

Year Released: 1985

The only reason this shoe isn't number one to me is because number one might be the illest sneaker of all time in any sport category, from just about every perspective. The Mac Attack launched at a time when John McEnroe was a maniac. If you look at the lineage of "rebel" ballers—the Agassi stuff that followed, any "I'm not a role model" conversation around Charles Barkley, Dennis Rodman's weirdo-ness, AI, any of them really—the first one that matter to me was Johnny Mac. This man was a prodigy (and a brat, and a whiner and an asshole) and he knew it and didn't give a fuck. This is what swag looked like in 1985. Nike's leveraged McEnroe's attitude with things like the "Rebel with a Cause Poster" which pictured Mac walking in the rain in a black trench, looking like he was about to kill (or just killed) the president. Hard. The Mac Attack came in one color. No pandering to the consumer. Grey and black, Mac checkerboard tongue. Very Gotham. Very clean. This is the colorway we are going with, and you will buy it. Say, word. The Mac Attack has never been reissued, unless you count the Nike Manor, which you should not. It is a very loose lifestyle interpretation. There was a version of the Mac Attack with a grass court bottom. I have never seen that shoe in person. You would have to ask Ray the Sneakerpimp about that (if you can find him).

1. Nike Air Trainer Hi

Year Released: 1987

The first time I saw the Air Trainer Hi, I think I think I might have had a small stroke. I distinctly remember having some sort of sensory crossover and wanting to taste the shoe or something. I thought it would taste like marshmallows and mint leaves. Right. Enough about that. These shoes did have a very strong smell though, that has always defined fresh out the box for me. The 2002 re-issues had the same smell. I almost passed out. When reissues popped, I was fiending so badly, that despite having knocked my back out of wack a couple of days before, I loaded up on painkillers and took a car service to Fulton Mall and back. I went home with four pairs, because I wanted to be able to wear this shoe for the rest of my life.

The Air Trainer Hi is so plush, so soft, so comfortable that it's almost like wearing bedroom slippers that perform. The price you paid for this privilege is that you could melt through the outsole in under a week. I wasn't caring though. When this shoe launched, it was confusing to me. I didn't know what it was. I think that was the genius and the risk of launching a "cross-training" category/product. Was it a tennis shoe? McEnroe wore it. I always called them McEnroes. Andre Agassi wore them and so did Vitas Gerulaitis and Mats Wilander. Maybe it was a basketball shoe. It was a mid, and it appeared to have a lot of cushioning. I've seen a number of shots of Jordan wearing it chilling after practice. Maybe he wore it to practice too. It was also deceptively light. You could definitely run in these. Maybe they were just street shoes. Cash Money wore them on his album cover. A lot of people still think of it as the Bo Jackson, and Bo knew a lot of things. Maybe it really did cross into everything.

Point is, the shoe and the entire initiative was going to do one of two things: either (a) be Lou Roe— a tweener—great little shoe, but not clearly “this” and not clearly “that” and ultimately very confusing to the consumer; or (b) convince the consumer that whatever you wanted to do, the Air Trainer Hi was just right for that. From my perspective, what kicked it over into option (b) (aside from the stellar marketing) was flawless design by Tinker Hatfield. There are a lot of articles on the design inspiration and process for this shoe. I think the biggest change was the move to the more prominent and traditional toe overlay. The original design for this shoe, and some of the player samples, had a plain toe that reflected the prevailing training/workout look of the era. It looked a little bit, um, aerobicized. At some point between sample and production, the toe changed to a more traditional overlay construction. To me, this made the shoe speak not only training and exercise, but also basketball, running, tennis, etc. Perhaps more importantly, it made what was a very aggressive, new and innovative looking shoe slightly less risky for the kid to wear on the block. That's big, because all of a sudden the shoe moves from performance to lifestyle. Purchasing decisions move from need-based to want based. And I wanted every fucking color. The Air Trainer Hi came in more colorways than you think too, including two different all-over black elephant print versions. Ultimately, the Air Trainer design language set the stage for most of what Nike did from 1988-1994, crossing over into basketball and inspiring things like the Jordan III. If I had to wear one shoe for the rest of my life I would wear the Air Trainer Hi.