Image via Complex Original
Being a celebrity automatically puts you under scrutiny for almost every decision you make and if you rock some fly kicks once, it is expected on a daily basis. Money doesn't always buy you style, even celebs with the deepest pockets get caught slippin'. We decided to put a gallery together of some, well, unusual footwear choices made by celebs that were caught on camera. Hit the jump to check out 50 Celebrities Who Made Sneakers Look Worse and let us know who else needs to step their game up.
Timberlake Boots
Sorel Caribou Boots
Who: Justin Timberlake
Timberlake has been known for supporting Nike and Jordan Brand on a regular basis, never trying too hard or anything over the top — just a steady rotation of clean classics. When JT was caught on set with Cameron Diaz rocking Sorel boots it wasn't exactly the former-N'Sync frontman's best look — unless there was a blizzard coming. Far from bringing sexy back, homie.
Westbrook Skates
Air Jordan III "True Blue" Custom Skates
Who: Russell Westbrook
Westbrook has been putting defenders on skates for a few years in the league but he didn't have to take it literally by getting a custom pair of "True Blue" IIIs to hit the rink in.
Mandy Moore Bape
Bape Bapesta
Who: Mandy Moore
At no point in her existence has Mandy Moore's street style ever been a point of conversation in the blogs, so when she popped up in 2009 rocking Bapes we doubt she even knew what she had on her feet.
Situation Yeezy
Nike Air Yeezy "Net/Net"
Who: Michael Sorrentino
The cast members of Jersey Shore stepped their respective sneaker games up significantly as the shoe went own and their pockets got fatter but The Situation still somehow made the first Yeezys look bad. They are Yeezys, right Gawker?
Budden Custom
Nike LeBron X "LeBronboutins" Custom
Who: Joe Budden
Mache and Budden have a history of dope custom collabs but 'Brons and 'Boutins are better left for Budden and Kaylin Garcia's Instagram collabs.
Snooki DC
DC Court Graffik
Who: Snooki
Snooki don't know shit about our culture. *Dame Dash voice*
Magro Jordan CMFT
Jordan CMFT Viz Air 11
Who: Ronnie Ortiz-Magro
Jordan Hybrids can be real hit or miss and Jersey Shore bros rocking them doesn't exactly help them get real street credit.
Drake Custom
Air Jordan V Custom
Who: Drake
When 'YOLO' goes wrong.
Bryan Cranston Chucks
Converse Chuck Taylor "Breaking Bad" Customs
Who: Bryan Cranston
Breaking Bad is the shit but when Cranston rocked some custom Chucks paying homage to his own character on the show—well, we're cool with these staying one-of-ones.
Magro Nike Dunk
Nike SB Dunk High "Thrashin'"
Who: Ronnie Ortiz-Magro
Camo shorts x Nike Dunks — we already told you this doesn't make you a sneakerhead.
Vinny Jordans
An Assortment of Air Jordans
Who: Vinny Guadagnino
The Gotti Boys remixed have, dear God, somehow become people who other people look up to. Or at least look out for. And after season one we noticed the kings of Seaside Heights had stepped their sneaker game up immensely. We can't really knock Jordans but the corny photo had to be called out.
Usher Zebra
Diet Butcher Slim Skin Zebra Print Sneakers
Who: Usher
At no point should your shoes look like something a teenage girl would rock on her feet or use as a seat cover in their first whip.
Situation adidas
adidas AR 2.0
Who: Michael Sorrentino
Dog, this whole outfit is one complete fail.
KH Jordan V
Air Jordan V "Independence Day"
Who: Kris Humphries
Thanks to his 72-day marriage to Kim Kardashian, his name has been relevant for the first time outside of the Garden State. If any company is lacing him with extra kicks due to his short-lived Kardashian fame that’s so lame, almost as lame as subpoenaing Kanye with a Nordstrom's gift. But we gotta give him props on that Foot Locker spot, at least he has a sense of humor.
Willow Stars Stripes
Stars & Stripes Sky-High Sneakers
Who: Willow Smith
The Spice Girls definitely would have rocked these if it was 2012 and they were American. Is Willow too old for her parents to still dress her? Just a thought.
Sorrentino Jordan SC
Jordan SC-2
Who: Michael Sorrentino
Not like you should be surprised, The Situation pops up on this list a few times for his blatant horrible style and bad taste in just about everything.
McCoy Radii
Radii 420
Who: Travie McCoy
If Hov couldn't make Radii hot, Travie isn't getting it done.
Soulja Yums
Yums x Soulja Boy
Who: Soulja Boy
When rappers get their own sneaker it can cause mass hysteria or just be hysterical. We can't front, at one point everything Soulja Boy did was being emulated by more than a few people but even the kid couldn't get people to get on board with his Yums campaign — even Master P had to laugh at that.
Situation Reebok Zig
Reebok ZigActivate
Who: Michael Sorrentino
For a minute we thought The Snitchuation had a Reebok deal since he kept popping up in the Zig technology kicks. On second thought there is no way a brand would ever think this would help them move units.
Wentz Yeezy IIs
Nike Air Yeezy II "Solar Red"
Who: Pete Wentz
Fallout Boy was dope — Kanye even jumped on a remix at one point — but we still can't figure out how Pete ended up with a pair of Yeezy IIs at the same time as many more deserving types (unless they worked out some sort of quid pro quo deal in advance). Dude can't afford Jason Markk? Pete beat the hell out of those IIs, no respect.
Wentz Uggs
Ugg Boats
Who: Pete Wentz
Pete Wentz had the Yeezy II connect before just about anyone outside of 'Ye's clique and dude usually comes correct with Vans and Commes des Garcon collabs as well, but the yeti-inspired Uggs? Pass.
Pauly D Reebok Zig
Reebok Zig Dynamic
Who: Pauly D
Pauly D took the all-black mantra a little too far and the Reebok Zigs paired with the Nike socks is always dreadful to witness, cross-branding at its worst.
Cannon JS Wings
adidas Originals x Jeremy Scott Wings 2.0 "Stars and Stripes"
Who: Nick Cannon
Jeremy Scott's Wings are one of the illest concepts in the past decade but Nick Cannon's corny ass was trolling when he rocked them on the court All-Star Weekend.
Wayne Boots
Forxfex Moon Boots
Who: Lil Wayne
Wayne style fails could easily outweigh his better moments but few decisions were more, um, "interesting" than his boot phase in late 2011. "The Motto" was one of his strongest verses since he got released from the pen, but in the video homie could have done without the leggings and moon boots that looked like they got slimmed on a Nickelodeon episode of Pete & Pete. Even Weezy's biggest fans couldn't defend their man on this one, Tunechi!
Pauly D Nike Dunk
Nike 6.0 Dunk High
Who: Pauly D
This is the primary reason the word 'swag' died in 2012, thanks DJ.
Westbrook Jordan V
Air Jordan V "Tokyo 23"
Who: Russell Westbrook
Steve Urkel 2013.
Frazier Boots
Custom Boots
Who: Walt Frazier
Walt "Clyde" Frazier has always marched to the beat of a different drummer — or maybe a completely different instrument. And for a guy who has been known to wear cow-print suits, these zebra-striped cowboy boots aren't too far outside his lane. Zach Galifianakis doesn't seem to know that, though.
JWoww Nike Air Max
Nike Air Max 2012
Who: JWoww
At least no one tried to tag this #ChicksInKicks.
Cruz Jordan V
Air Jordan V “Bin 23”
Who: Victor Cruz
Cruz was on his suit and tie shit but he probably should have stuck with some real black dress shoes instead of the premium Jordan Vs.
Malone Sketchers
Skechers Shape-Ups
Who: Karl Malone
On the court Malone may be one of the best to hold down the four-spot but his personal decisions have always been a bit odd. After he left the league he decided to endorse Skechers Shape-Ups, a shoe synonymous with middle-aged women who loathe working out (You can bet Malone earned his own physique the old-fashioned way). We don't care how short Stockton's shorts were, he has more street cred than Karl after this one.
Deena Free Run
Nike Free Run +2
Who: Deena Cortese
Why is Deena dressed like she is going to the gym when we all know she is going to pound shots instead of track a few miles in the extremely comfortable Nike Free Run +2. Too bad she doesn't have a matching Fuel Band to let her know her true worth.
Jay Nike RT1
Nike RT1
Who: Jay-Z
The swag don't match the sneakers. The light blue ripped jeans and jean jacket actually look pretty dope but then mix in the brown Nike RT1s and it just kills the whole vibe, not one of Jay's better looks.
Sinbad Wade
Jordan Fly Wade 2
Who: Sinbad
A Sinbad sneaker spotted is pretty random in itself but when he stepped out rocking Jordan Fly Wades just a month after D. Wade himself quit rocking the shoe—awkward. Someone really couldn't have hooked him up with something a little more current?
Diddy Upper
Upper Echeleon Sneakers
Who: Diddy
Diddy told us he won't stop but can someone tell him to toss these faux-gold rope chained sneakers and fire whoever picked the joints out.
Rita Jordan XII
Air Jordan XII "Obsidian"
Who: Rita Ora
Typically Rita is the queen of pairing Js and sexy outfits but she just had way too much going on here.
Houston AF1
Nike Air Force 1
Who: Marques Houston
What is wrong with a pair of Uptowns? Nothing. But when Marques Houston let that House Party fame go to his head and rocked a clear suit with his white underwear essentials he ruined a classic for everyone. Even Nelly didn't take it this far.
Pharrell Boots
Nike Snowboarding x Arbito Zoom Force 1 Boots
Who:Pharrell
Pharrell is a G when it comes to style but still we couldn't get down with the over-sized snow boot movement, even if they were Nike. Skateboard P transformed into Ski Lift P, and with that bubble vest he looked like he was ready for the Winter Olympics.
Wayne Supra
Supra Skytop Custom
Who: Lil Wayne
Usually custom kicks end up having people gassed on sneaker blogs wishing they had the proper connect but Weezy's Wizard of Oz looking Skytops were straight up embarrassing.
Will Smith adidas
adidas Superstar
Who: Will Smith
The Fresh Prince proves, contrary to popular belief, that white-on-whites actually DON'T go with everything.
TPain Spizike
Air Jordan Spizike "University Blue/Vivid Orange"
Who: T-Pain
The over-matching of the jacket and the kicks? We hope dude lost his luggage and had five minutes at Foot Locker before the event because that's about the only acceptable excuse.
McCoy Spizike
Air Jordan Spizike "Black/Cement"
Who: Travie McCoy
McCoy took Fat Joe's patent sneaker loving and remixed the move by biting a pair of his crisp new Spiz'ikes. There has to be a better way to show off your new joints then putting them in your mouth. This one shamed sneakerheads everywhere.
Jordan Jordan III
Air Jordan III "Cement"
Who: Michael Jordan
We appreciate everything you have done for us Mike but damn, can't someone help you pick out a pair of jeans that didn't come out in 1998?
Cruise LeBron VII
Nike Air Max LeBron VII
Who: Tom Cruise
Nothing against the LeBron VII, we stacked up on these thinking The King would earn his first ring in them. But shortly after Tom Cruise declared his love, fuckin' up couches Rick James style, he was out in a button-up, sweats, and Brons with a IDGAF attitude.
Trinidad Christmas
Nike LeBron X "Christmas" and Nike Zoom Kobe 8 "Christmas"
Who: Trinidad James
No doubt Trinidad is doing his thing and much respect but pulling out one "Christmas" LeBron and one Kobe sneaker for a game — hypebeasts we know about ya, don't buy shoes unless they popular. Next time let's keep it simple man, you went from spotted to sonned.
Nas Jordan IV
Air Jordan IV "Black/Cement"
Who: Nas
Over-matching your sneakers and gear is bad enough but Nas could at least have gotten the right retro.
Jay-Z Radii
Radii Moon Walker
Who: Jay-Z
During his big push marketing The Blueprint 3, Jay started consistently rocking the Radii Moon Walker. The sneaker had the same look as Supras but for whatever reason they seemed too forced and never really caught on, even with a Jigga Man co-sign.
The Dream Tom Ford
Tom Ford Leather Riding Boot
Who: The Dream
Christina Milian should have known from the jump this marriage was doomed, especially when Terius showed up to the altar looking like he came straight from a polo match.
Gil D&G
Dolce & Gabbana High-Top Sneaker
Who: Gilbert Arenas
Gil had the Internet going nuts when he rocked a pair of Velcro D&G on the court for the courtside celebrities at The Staple Center to see — always strapped.
Flo Hyperfuse
Nike Zoom Hyperfuse 2011
Who: Flo Rida
Manpris and a camo tank — the kicks never even stood a chance.
Omarion Mad Foot
Omarion x Mad Foot OBOI
Who: Omarion
You don't remember these? You're not alone. The Japanese brand linked up with "O" after he signed with Young Money (forgot about that too?) in hopes that he could turn those B2K boy band numbers into sales. The design left a little to be desired and the strap looked like a straight jack from Kanye's Ato Matsumoto and Nike Yeezy movement.