Image via Complex Original
The 1992 film White Men Can't Jump was a celebration of the trash-talking, flashy hustlers of Venice Beach that balled their way into making a living on the blacktop. Woody Harrelson, Wesley Snipes, and players of all shapes and sizes were all just trynna make a buck, but everyone who showed up at the court also made sure they looked as fly as possible.
The people who created this film may not have realized it at the time, but they created a perfect time capsule of early '90s style. White Men Can't Jump not only provides a great look into the street ball culture of the West Coast, but also had every single character and even the random bystanders and extras rock dope gear that are emblematic of their time and place. From Sidney's cycling caps to Billy's wild prints and everything in between, these are The Best Outfits From White Men Can't Jump.
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Random Old Man keeps it cozy during his Tai Chi session.
Worn by: Venice Boardwalk Bum
The second shot of the film is this old dude practicing some early morning Tai Chi on the Venice Boardwalk. He's draped in amazing old man style, including some straight leg chinos, white trainers, and a cozy athletic crewneck with navy detailing.
Old man floral steez might make this guy the most stylish Venice Beach Boy.
Worn by: Venice Beach Boy Member
While crooning over the opening credits, this member of the Venice Beach Boys sets the bar high for the rest of the film's style. In a floral shirt under a bomber jacket, oversized frames, and a crazy hat that only an old man could pull off, every other character in the film immediately has their work cut out for them to get on this guy's level.
This version of geezer style in the '90s perfectly struck the balance between comfy and classy.
Worn by: Venice Beach Boy Member
Finding the middle ground between the casual old man look and the suit and tie shit of the other two Venice Beach Boys, the bassist of the group rocks a buttery-looking powder blue cardigan over a simple shirt buttoned all the way up. Take notes, young'ns.
The third member of the Venice Beach Boys keeps it sharp as a tack.
Worn by: Venice Beach Boy Member
As the suit-wearing one in the group, this Venice Beach Boy brings an air of class and sophistication to the trio, balancing out his bandmates.
This Stussy 8 Ball sighting is the film's best cameo.
Worn by: Venice Boardwalk Skater
Within two minutes of the film starting, this awesome Stussy 8 Ball T-shirts makes its way past the camera as a kid skates down the Venice boardwalk. Seeing this now probably makes Stussy go, "Been in this shit since '92, look at all the bullshit we been through."
This faceless man is Theophilus London's style inspiration.
Worn by: Random Fan at Venice Beach Courts
He's a faceless, nameless fan in the stands, but this guy has some serious style. A Felix the Cat T-shirt under a classic motorcycle jacket, along with some ripped up white denim and Danny Brown teeth means this dude has seriously unique style.
This random fan's style is the embodiment of early '90s hippie vibes.
Worn by: Hippie Fan
With his drugrug hoodie, big bushy beard, stonewashed jeans, and giant sunglasses, it's pretty clear why this dude would rather focus on acquiring Cap'n Crunch than play some streetball.
Here's one look that should stay in the early '90s.
Worn by: Old Man Baller
Believe it or not, this was how some dudes dressed to play ball in the early '90s. Maybe by wearing this crop top T-shirt and bike shorts, he was strategizing that no one would want to box him out.
Sidney's flashy style is a reflection of the way he balls.
Worn by: Sidney Deane
Sidney is the self-proclaimed king of the court, and his style is a fusion of athletic gear, flashiness, and pure bravado. On the court, he typically rocks bicycle shorts, two tank tops, a cycling cap, and a fresh chain. Dope style that outshines his opponents no matter what the outcome of the game is.
Walter brings a positive message to the court.
Worn by: Walter
He may be Sidney's enemy on the court, but Walter knows he and Sidney are fighting for the same cause. With his Malcolm X "UNITY" T-shirt, Walter brings an afrocentric element to the court, and does it in style.
If only Junior's court skills matched his oversized jersey game.
Worn by: Junior
He's too skinny to ever be a truly great player, but his frail frame makes this oversized Jordan jersey look awesome. If only his ball skills could catch up with his style, then he might have a shot at hustling up some money on the court.
A random bystander in the crowd rocks the trippiest look in Venice.
Worn by: Random Trippy Bystander
He's just an anonymous face in the crowd, but this dude stuns on everyone in Venice in his sleeveless poncho T-shirt. The look is rounded out with serious dreads, reflective shades, and high-waisted pants with the shirts tucked in.
George proudly shows off his nerdiness on the court.
Worn by: George
He may not be the best baller on the court, but George has other loves in life, including comics. The most stylish part of this Punisher T-shirt is that he doesn't give a fuck if it's nerdy; he's showing off what he loves with pride.
True weirdo steez was at its peak in the '90s.
Worn by: Weirdo Bystander
This bystander in the crowd of Billy's debut game merked it in an insane manner with the geriatric sunglasses, pith helmet, and varsity jacket. Very weird. Very '90s.
The apple of style doesn't fall far from the tree.
Worn by: Sidney Dean's Son
Sidney Deane's son has a bright future ahead of him. In his first appearance on-screen, he has a sick Levi's cycling cap on, and we're sure he'll be the most stylish dude in the film if there's ever a sequel.
Billy establishes his signature look in his first game at Venice Beach.
Worn by: Billy Hoyle
His tie-dye cap, worn out "PARENTAL ADVISORY" crewneck, and wild atlas-type shirt may make some people automatically assume he's a chump, but that's all part of Billy Hoyle's style. And, to be honest, this is a crazy but kinda awesome look.
A fan in the background has country club swagger.
Worn by: Country Club Extra
Billy and Sidney are about to go at it in a shootout, and this dude is calmly and cooly fittin' to watch from the sidelines. This dude immediately signals #wealth, as he effortlessly drapes a sweater over his shoulders his last name is Kennedy.
Even the random bettors in the crowd look dope.
Worn by: Sideline Bettors
As Billy and Sidney have a one-on-one shootout, the bystanders start betting. But with snapbacks, fresh eyewear, and each of their jackets, neither of these dudes could truly lose.
Billy's not the only white guy on the court with style.
Worn by: Random White Bystander
Who knows if this guy could run with Billy and Sidney, but his style is definitely at their level. In the black tank, backwards black snapback, and patterned shorts, dude is killin' it in the background.
Sidney keeps his style consistent with this muscle man steez.
Worn by: Sidney Deane
In their first true hustle, Sidney stays consistent with his court style in a muscle tank and cycling cap as he and Billy win $250 and a diamond necklace from their opponents.
Raymond has an awesome "in your face" shirt that matches his insane personality.
Worn by: Raymond
As one of the biggest players on the court, Raymond knows he doesn't have to put up with anyone's shit. His homemade tank top originated as a T-shirt that says on the front, "You can talk the game," and finishes on the back with, "But can you play the game?" T-shirts with attitude were all over in the '90s, and Raymond was very on top of this trend.
This baller's striped tank over the solid tank is a very advanced move that most can't pull off.
Worn by: Random Baller Enjoying Himself
We don't necessarily advise that you try this, but this dude was able to pull it off. The two tanks look is something that is definitely Sidney's signature move, but that doesn't mean other people can't rock it well.
Raymond's teammate rocks a tank showing his Ghanian pride.
Worn by: Raymond's Teammate
Just because he's playing ball doesn't mean he can't show love for another sport. With red, yellow, and green flag flying high, Raymond's teammate displays his fandom of other sports and the country of Ghana.
Billy intentionally rocks clothes that mark him as a chump.
Worn by: Billy Hoyle
With his tie-dye cap and torn up clothes, Billy cements the general assumption that he's a chump. He definitely uses his worn-out gear to his advantage, as he and Sidney hustle their way to becoming kings of the court.
This fan watching a razor blade attack is wearing the most '90s overalls outfit possible.
Worn by: Amazingly Dressed Extra in the Background
Everything about this screams early '90s. The lightwash overalls, the oversized T-shirt with patterns on the sleeves and collar, and that mullet. When future civilizations are teaching their children about 1992, this is the picture they'll point to.
Sidney cleans up well off the court.
Worn by: Sidney Deane
When he's away from the blacktop, Sidney proves he can clean up well. In this powder blue long-sleeve polo, he makes an appearance as a classy potential buyer for a house out of the 'hood. The only question is if he can scrounge up enough cash from his hustling and contracting jobs.
Billy puts on for his favorite musician.
Worn by: Billy Hoyle
Despite Sidney's claims that Billy can't truly hear Jimi Hendrix, Billy shows up rocking a Jimi tee under a dope button-down.
This bystander has an amazing political T-shirt on.
Worn by: Politically Conscious Bystander
Malcolm X is saying to MLK, "Well Martin, we tried. I wonder who's going to take our place?" Another incredible example of the afrocentrism that was on full display in the early '90s.
This random courtside fan was putting on for his city and for his cause.
Worn by: L.A. Raiders Fan
In the early '90s, afrocentric gear was everywhere and was actually some of the freshest stuff out there. This "Black by Nature, Proud by Choice" T-shirt spread the message loud and clear, and his L.A. snapback is something you'd see the A$AP Mob rocking today.
Sydney channels His Airness.
Worn by: Sidney Deane
Sidney, meanwhile, shows up dressed to do business. The red muscle tank, Jordan shorts, and black wristband signal to everyone who he plans on channeling on that day's hustle.
At this point, Magic Johnson still trumps Jordan.
Worn by: Zeke
Even though Jordan was beginning his reign in the early '90s, Magic was still considered his better at this point in time. And so, rather fittingly, the team with the Magic Johnson jersey beat Sidney and Billy...kinda.
Robert's style is purely functional, which helps him and Zeke beat Sidney and Billy.
Worn by: Robert
In a no-nonsense tank top, shorts that won't get in the way with their bagginess, and bike shorts, Robert leads his team over Billy and Sidney, and into a cool $1,700.
Sidney's entire crew has fresh style off the court.
Worn by: Zeke, Junior, Sidney, Robert
Billy realizes that he was, in fact, hustled by Sidney. He runs up on Sidney and his crew while they're watching basketball at Sidney's crib. While he stumbles onto the plan, he also stumbles onto a crew that's repping '92 style perfectly. Whether it's Zeke, Junior, Sidney, or Robert, copy any of these outfits and you'll be dressed in a dope throwback look.
Everyone knows the tournament organizers are squares because of their boring suits.
Worn by: Tournament Organizers
In a film full of flashy style from the streets, these organizers of the "Brotherhood Tournament" stick out as having the most boring and white-bread style. In matching jackets and ties, they're more concerned about the sponsor money than anything else, including looking good.
Afrocentric heads keep it funky fresh in the crowd.
Worn by: Fans at the Brotherhood Tournament
These three fans are in the audience at the corporate sponsored "Two-On-Two for Brotherhood Basketball Tournament," a name and concept these down-ass dudes shake their heads at in disgust.
Billy dresses like a chump, but balls like a champ.
Worn by: Billy Hoyle
Billy trash talks his opponents at the tournament like never before, which takes serious balls since he's doing it in a dolphin T-shirt. That's why style is all about attitude; even when you're in a shirt that should make you look like a pussy, you can still look good with the right swagger.
Sidney proves that consistent style has its strengths.
Worn by: Sidney Deane
Even if he and Billy hadn't won, Sidney would've come away with the best-dressed trophy from the Brotherhood Tournament.
Sidney and Billy stay cozied up while cooling down between games.
Worn by: Billy Hoyle and Sidney Deane
In between games, Billy and Sidney stay steezing on the sidelines. Billy gets real cozy with the towel, and Sidney's matching sweatsuit flexes on all the chumps watching from the crowd.
This chump rocks a crazy mullet.
Worn by: Brotherhood Tournament Player
This Patrick Swayze-esque 'do will hopefully never resurrect itself after the early '90s (though we've definitely seen people try). We're not saying this dude lost because of his hair, but it just doesn't seem very aerodynamic.
Sidney keeps it business casual for his day job.
Worn by: Sidney Deane
Tanks don't cut it in the professional world, so when he's dealing with potential clients for his roofing and contracting gigs, Sidney rocks the baggy shirts that dominated the early '90s. The cut may have slimmed down, but this burgundy corduroy would still kill it today.
The Stucci brothers dress like stereotypical '90s villains in long trenches and mullets.
Worn by: The Stucci Brothers
They're not the most terrifying bad guys, but their style is pretty horrendous. You'd think that with all the money they're strong-arming out of people, the Stucci brothers could buy some new threads.
Zeke's Magic Johnson wardrobe is pretty impressive.
Worn by: Zeke
In the second game of Zeke and Robert, Zeke again outdoes his teammate in terms of style. It's pretty clear who Zeke's favorite player is, and he ain't afraid to show it.
This Run DMC T-shirt sighting is a hidden gem in the film.
Worn by: Random Baller
This dude was just trying to see if Billy could hit a half-court hook shot. But his classic T-shirt caught our eye. Is it tie-dyed?
Alex Trebek's suits revel in '90s style.
Worn by: Alex Trebek
This might be the most stereotypically '90s outfit in the entire film. Alex Trebek's drab green double-breasted jacket with enormous peak lapels is something that will be forever associated with the last decade of the 20th century.
Do bowties make you smarter?
Worn by: Leonard Allen
Now normally we don't co-sign bowties, but Professor Allen gets a pass since he's a prof. Unfortunately, the bowtie only made him look smart; he lost miserably to Gloria.
Gloria's competitor loses Jeopardy, but he wins the style round.
Worn by: Richard Andrews
Burgundy suit and brown floral tie? Takes serious cajones to try and pull this off. It might've worked if he had switched up the hairdo.
Sidney and Billy tone down their style at Jeopardy.
Worn by: Sidney Deane and Billy Hoyle
While cheering on Gloria, Sidney and Billy keep their style relatively restrained. Still though, the buttery purple shirt on Sidney and muted teal on Billy prove that their steez doesn't suffer off the court.
These eyewitnesses may not have seen anything, but they're definitely guilty of rocking dope gear.
Worn by: Eyewitnesses at the Vista View Robbery
These kids were just hangin' out looking fly as fuck when police rolled up asking if they had seen anything. Even if they had, they followed the snitches get stitches protocol and continued to floss freely.
Billy has the perfect kit for a casual bike date.
Worn by: Billy Hoyle
After Billy and Gloria make up, they cruise down the Venice boardwalk as the adorable couple they always were. Billy has the perfect outfit on for a casual bike ride-cozyboy hoodie and some wild printed shorts, all rounded out with the high-top Pumps.
Wild prints, bicycle shorts, and doubling up on tank tops. In their final game, Sidney and Billy's style shines through.
Worn by: Sidney Deane and Billy Hoyle
In the final game against playground legends Duck and the King, Billy and Sidney unleash their sickest ball yet, as well as their best steez. Sidney's standard look of double tanks, cycling cap, and bike shorts makes its final appearance, and Billy flips his tie-dye cap around one last time. The two of them run through the competition, and laugh their way into some serious dough. Hopefully the new gear they cop won't change their style up too much.
Even though Duck is over the hill, he was still on-trend with his steez.
Worn by: Duck Johnson
Neon bike shorts? Checkk. T-shirt tucked into shorts? Check. Even though Duck Johnson and the Edding "The King" Faroo were getting on in their years, they were still dressing like the young dudes they were balling against.
Eddie "The King" Faroo puts on for his hometown Dodgers.
Worn by: Eddie "The King" Faroo
It might be a sign of showing his age, but "The King" rocking an '88 World Series Champions tank top of the L.A. Dodgers is a dope move to bring to the court. Hands down, hometown pride will always be a good look.
These bettors on the sideline have serious bawse style.
Worn by: Sideline Bosses
The most serious competition that Sidney and Billy face comes from the style of two dudes betting on their final game from the sidelines. These two are serious Dons, and exchance serious scrilla a few times as the game goes back and forth. With their gold game on lock, fresh Cazals, and bawse suits on, these two anonymous betters definitely know how to enjoy the finer things in life.
A third bettor joins the other two, and his style makes a claim for the throne of dopest looking dude in the film.
Worn by: Third Sideline Bettor
His round frames, oversized shirt, off-center belt, and pager (of course), this dude is clearly a hotshot in L.A. with the style to match. We're not sure who he's betting on, but if he wins he'll only floss harder.
The Stucci brothers strike again, and at least look a little bit better.
Worn by: Stucci Brothers
The Stucci bros make a second appearance, and they definitely hit up a shop or two since their last time on screen. They clearly won't outdress Sidney and Billy, but hey, that's tough to do when your garments of choice are early '90s suiting.
Even if their friendship had its ups and downs, both dudes are consistently stylish.
Worn by: Billy Hoyle and Sidney Deane
In the final scene of the movie, we see Billy and Sidney survive and prosper, as well as steez out in their signature looks. Billy's suede bomber jacket consistently appeared throughout the film, but looked its best here over a grey crewneck and sun-bleached shirt. Sidney rocks one of his signature cycling caps, and pledges his allegiance to the cozyboy life in his matching sweatsuit.