Style

The Worst Style Fails From the Most Stylish People

Nobody's perfect.

Not Available Lead
Complex Original

Image via Complex Original

Men lie. Women lie. Cameras don't. We are blessed with photos of some of our favorite stylish entities, whether they're paparazzi shots, editorials or just a good ol' Instagram selfie, showing off their latest fashionz as much as possible. We constantly praise the trendsetters as they embark on the tough task of leading followers into a world of stylish enchantment, but sometimes (yes sometimes!) not even the most stylish get it right.

Sometimes they just hadn't figured out their personal style yet and were going through an experimental phase. Other times they were following trends that they probably should have passed on. It's all good—players fuck up too sometimes, but that doesn't mean we can't poke fun at their past transgressions. You already know these guys kill it on the regular, but here are some of today's best-dressed men in a way you haven't seen them before. These are The Worst Style Fails From the Most Stylish People.

RELATED: The 50 Most Common Style Struggles
RELATED: 8 Menswear Trends That Designers Hate
RELATED: How to Know When Your Terrible Style Needs an Update

Kanye West is the Rap Game Bagger Vance

What went wrong: The V-neck sweater lets his collar flatten out like a pancake. And the pattern screams "Grandpa!"
One quick fix: Opt for a solid crewneck sweater.

Ye's hand over style definitely had some arthritic moments. And to think; people actually dressed like this to mimic him?

Advertisement

Joseph Gordon-Levitt as a Less Stylish John Wilkes Booth

What went wrong: His hair is all over the place, and those sunnies aren't doing him any favors either.
One quick fix: Switch to more classic shades like Wayfarers, and brush your hair.

The dude has made some serious strides to join the stylish celeb ranks, but lest ye forget Tommy from "Third Rock From the Sun" lacked any semblance of style. Exhibit A.

Jay-Z Wears Baggy Cargo Shorts So His Knots Can Fit

What went wrong: Those shorts make him look like he's smuggling something.
One quick fix: Wear shorts that stop above the knee, without cargo pockets.

These shorts can handle any size wad of cash Jay-Z decides to carry. And his keys, his passport, his pride, his self-worth, etc.

Advertisement

D-Wade Dresses Like a D-Bag

What went wrong: The too big shirt, floppy tie, and ugly vest.
One quick fix: Lose the vest, get a shirt that fits, and keep the tie well, tied.

Too many levels of fuckery to just point out one deficiency.

Russel Westbrook is a Real Boy!

What went wrong: Quirky accessory overload.
One quick fix: Choose the suspenders, red bowtie, or hat—not all three.

Does that make Kevin Durant "Gepetto?"

Advertisement

David Beckham in The Matrix

What went wrong: His leather coat is way too shiny.
One quick fix: Opt for a classic, versatile fabric like navy or charcoal wool.

We're sad to see his legacy in soccer come to an end, but hopefully it frees up some time to make more stylish appearances...much unlike this shitshow of a duster he's wearing.

Orange You Glad to See André 3000?

What went wrong: Too many patterns; too much coordination.
One quick fix: A more subtle sportcoat would have worked, and there's no need for so much orange in the pocket square, tie, and pants.

3 Stacks needs to lay off the orange juice in this kit.

Advertisement

Jude Law Gets the "Cozy Boy" Look Totally Wrong

What went wrong: The sweatpants and flip-flops.
One quick fix: Toss on some raw denim and canvas sneakers and you're just as casual and way less sloppy.

Law looks like he's given up and decided to wear this outfit everyday for the rest of his life. Hopefully he's just in-between characters and said "fuck it" for the day?

Pharrell's Too-Short Tux

What went wrong: Too much black tie rebellion.
One quick fix: Go for a simple tux, and maybe add an accessory like a BBC fitted instead of a droopy beanie. But you can't go wrong with just a simple tuxedo.

While Pharrell seems to be ageless, some phases of his style we are glad real old, real fast.

Advertisement

Jon Hamm Is a Modern Don Draper

What went wrong: The scarf, the rimmed eyeglasses... it's just too much affectation.
One quick fix: Lose the scarf. Right now.

The ironic thing is that if Don Draper were an ad agency creative director today... he would actually dress like this. And probably live in Greenpoint, running a magazine about homebrews and rooftop farming on the weekends.

LeBron James Heading to the Disco

What went wrong: Do we seriously have to tell you?
One quick fix: Choose a more subdued color suit and accessorize with the color, not vice versa.

He was actually wearing this baby blue pimp suit to the club where he learned two of his favorite dance moves; the "Choke" and the "Flop."

Advertisement

Ryan Gosling Goes Too Deep

What went wrong: He let a little too much off his chest.
One quick fix: There's nothing wrong with a crewneck T-shirt.

Crazy, stupid shirt.

Theophilus London: Street Beatnik

What went wrong: The turtleneck completing the all-black-everything look gone wrong.
One quick fix: A regular black T-shirt with a jacket or a sweatshirt. Anything but a turtleneck.

Theophilus looks like an art major cast in his first play as an extra. "London, you will be playing the part of 'Tree #2'"

Advertisement

Nick Wooster Goes Street Goth

What went wrong: Way too much going on. We know Wooster has quirky style, but wtf?
One quick fix: Lose the spandex and boots, opt for an all-black sneaker.

Wooster looks his best in tailored looks, and he tried to mix that in with this street goth-friendly ensemble. But sometimes you have to go all in: AIN'T NO SUCH THING AS HALFWAY GOTHS, WOOST GOD.

Mos Def's Deafening MCM Ensemble

What went wrong: Branding overload... and a visor.
One quick fix: Go for a solid denim jacket, and a subtle but breathable 5-panel.

There aren't many NY MC's with stylish aptitude as advanced as Yasiin Bey, however fits like these lead us to believe he was lobotomized this day and this day only.

Advertisement

Justin Timberlake Be On His "Vest and T-Shirt Shit"

What went wrong: The hat, the vest, and the ugly necklace.
One quick fix: Ditch everything but the T-shirt.

How do you look like a page ripped from The Hipster Handbook? Wear everything in your closet at once.

Steve McQueen's Daisy Duke Moment

What went wrong: Shorts that reveal way too much.
One quick fix: Short length should go beyond your fingertips, but shouldn't exceed your kneecaps.

Who wears short shorts? Steve McQueen apparently. Imagine if your dad was walking around with these on. Yeah... pretty horrifying right?

Advertisement

Stay ahead on Exclusives

Download the Complex App