The Most Swagless People Who Are (Otherwise) Winning in Life

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Why he's winning: Living out the Vinny Chase day-to-day flourish IRL solely off of Entourage checks

Vincent Chase and Adrian Grenier is a true blue life-imitating-art scenario right down to dressing like he just rolled out of bed with a few women, still half-high and threw on whatever was the least wrinkled. And after a few months of "hard work" filming the Entourage movie to replenish that bank account, he's undoubtedly right back to the lax life.

Why he's winning: Made one of the best R&B albums ever, still probably eating off of it tbh

It seems like one day a couple years ago Usher just decided to start taking style risks: and failing at them. Here's a confession bro, you're not Pharrell, just give up already and stop ducking your stylist's calls.

Why he's winning: Storied career with the Yankees rivaled only by his storied hit-list

Honestly, who are we to even make one goddamn disparaging remark to this man. If the women on this list, representing only a fraction of his dime-piece pulls, don't give a fuck then by all means Captain, keep flourishing.

Why he's winning: Still thriving as leading man A-lister despite consistent Oscar curvature

Wow, you really have to kill it on screen as awesomely and consistently as the Cap does to avoid being ethered for being so swagless. This dude anointed his squad the Pussy Posse for crying out loud. And yet for all the slayage, the fearless leader dresses like a middle-aged suburban dad. Someone in the squad, please, speak out against the newsboy caps at the very least. But who's gonna risk getting ejected out of the Posse, though? No wonder dudes get worked in pickup games by old ass George Clooney, smh.

Why he's winning: Hollywood heartthrob, plus recently gained the respect of the male movie-going population after 21 Jump Street

Girls have been in love with dude since Step Up, and even though his star continues to rise to a point where people sometimes forget that's how he came up, he still dresses like he's in backup dancer mode in his downtime.

Why he's winning: Portrays the coolest bastard on TV

TV critics have noted that Jon Hamm likes to do a little comedy, like guest stints on 30 Rock or last year's Clear History, in between seasons of "Mad Men" perhaps as a detox from all the soul-crushing despair that show traffics in. So maybe dressing so sloppily is just another way to take a break from being the best-dressed men on TV? Because as soon as dude steps out of a suit it's an inexplicable nightmare.

Why he's winning: One of current Hollywood's reigning kings of comedy

Between starring in what seems like two must-see comedies per year, writing instant classics like Superbad and This is the End, Seth Rogen's got the comedy genre in the palm of his hand. And that's still not enough: soon all eyes will be on his hotly anticipated TV adaptation of the Preacher graphic novel on AMC. Maybe when he adds showrunner to his resumé he'll start dressing like he's killing shit.

Why he's winning: President of OTB, holding group that includes Maison Martin Margiela, Diesel, etc.

The so-called "Jeans Genius" is pretty fucking dumb when it comes to dressing himself. This dude has the Swagless European Creep look on full lockdown. Is Bad Boys 3 still happening? We got your new bad guy, right here.

Why he's winning: Buckets of money to play eccentric weirdoes no matter how tired audiences are getting of his shtick; engaged to the goddess Amber Heard

What happened to dude, seriously? This applies to both career and style. By now everyone's aware of the rut Johnny's lowkey been in since the Pirates franchise was poppin'. And off the screen, it's straight-up eyesore. Back when he was covering tabloids with Winona Ryder and then Kate Moss he was the swag god we all aspired to be. Now he's dressing like a freak show manager, like everyday life is a Tim Burton movie or something. But Amber Heard seems into it, so really, what do we know?

Why he's winning: His shitty movies keep breaking the box office

These days Sandler's bank account is filled with at least nine figures and exactly zero fucks. This guy just does not care in regards to...anything. The last time he put out a watchable movie dudes still dressed like this, and apparently he never stopped. But when Grown-Ups 2 makes a quarter billion, what can you really say?

Why he's winning: Won 4 Masters tournaments, White-Woman-Flourish-God

A career in golf just makes it so easy for a guy to let himself go. The only alternative is to wear the loudest polos and absurd prints or whatever it is those dudes wear on the green and make it work, but your boy Tiger was too focused on being the best out to worry about that shit (priorities). So here you have it, one of the leading black heroes and athletes of all time (and you're wack if you let shit like infidelity scandals mar that) dressing like Guy Fieri at a Las Vegas pool party.

Why he's winning: Facebook, second youngest (self-made) billionaire, duh

If there was ever a poster boy for not letting the money change you, it'd be Mark. Twenty-five of them beez and the god's still dressing like he can only afford Gap. Young Zuck, realer than your favorite rapper.

Why he's winning: Four rings

Props to the god for not trying to keep up with the young go-hards and their flashy post-game interview style, but there's a thin line between dressing your age and just letting yourself go. You can't be the captain of the team with the best record in the league and dress like an IT guy, b. Oh wait, four rings?  We'll shut up now.

Why he's winning: Sold Ed Hardy for $62 million, is worth more than $200 million

Honestly, is it really a shock that the "designer" behind such visual headaches as Ed Hardy and its self-titled spin-off, is pretty awful at dressing himself?

Why they're winning: Even in 2014, society is still set up to cater to them first and foremost

Middle. Aged. White. Guys. Billowing button up shirts tucked into boot-cut jeans that would've been out of style even in 1995, basic struggle polos, and a clothes buying history mired in expensive but basic department store struggle. Their anti-swag is as old and far-reaching as the history of them running well, everything. Some things [will] never change.