The 50 Worst Dressed Celebrities of All Time

Written by Susan Waits and Katy Lindenmuth.

There are plenty of famous people with great style. Whether they're killing it in a well-cut suit on the red carpet or embodying the idea of casual cool in a paparazzi photo, there's always that group of guys with style worth paying attention to.

And then there are the other dudes. The ones who keep horrible stylists in business and who regularly co-sign wack trends and brands simply because they don't care or don't know any better. Despite having the financial means and industry resources to look great, they don't. Sorry guys, you've just made our list of The 50 Worst Dressed Celebrities of All Time.

From wannabe gangster, to wannabe MMA fighter... Looking back, it seems that Vanilla Ice may have actually been the greatest, most elaborate ongoing prank in pop culture history. Seriously, a to-the-extreme rapper gets street cred when he's wearing star-spangled windbreakers and Hammer-esque pants? He was basically Robert Matthew Van Winkle's Borat, punk'ing America into wicked album sales and a Grammy nomination. Two decades later, though, it's still not clear who got the last laugh.

These days, this comedy writer is basically a baller in the entertainment industry — he's won SIX Emmys and, as much as the Oscars suck, “Academy Awards Head Writer” looks pretty cool on your résumé. But his trademark chubby, schlubby look — offensive tee shirts, a few extra chins, hair that needs a good deep conditioning — worked only in the '90s: He was in the public eye then, but doing stand-up... so people were supposed to laugh at him anyway.

The consummate three-piece suit trendsetter, Deion Sanders paved the way for sportscasters the cable networks over to flood our screens with nauseating monochromatic-striped suits and colorblocked shirt-tie combos. But the only thing that might be worse than Sanders' 17-inch Windsor knots is his 1994 hip-hop single “Must Be the Money.” Google it.

Say you're worth, oh, $17.5 billion. Would you wear a hoodie, old tee shirt, and adidas sandals every day? Mr. Facebook will probably protest that fellow zillionaire Steve Jobs wore a simple black turtleneck every day… but we did some research, and Steve's go-to getup was not too shabby — those Issey Miyake-designed suckers cost $175 a pop.

Although he's lost the feather hair extensions (and really all of his hair) as of late, Boy George is still powering through his commitment to neon-purple eye liner and a high hat, thirty years post-Culture Club. Sorry, dude, Elton John cornered that market when you were still a sexually confused third grader.

Who wouldn't want to sex up a neo-New Kids quartet of racially diverse randoms from Oklahoma? Not even if we added in post-dated George Michael-bangs, multicolored leather bombers and stonewash jeans? But if for nothing else, at least Color Me Badd inspired a portion of "Dick in a Box" — and for that we thank you. What were your names again?

It might seem harsh to put a couple of relatively forgotten child stars on this list, but remember: Chris “Mac Daddy” Kelly and Chris “Daddy Mac” Smith were responsible for thousands of little twerps dressing ass-backward in the '90s. If you were one of them, and there's photographic evidence that hasn't yet been destroyed, maybe it doesn't seem so harsh now, does it?

There's really not much to say here, guys. Thirty years of striped hot pants, bedazzled tank tops and white slouch socks seriously just speaks for itself. But the actual issue at hand is the fact that any aging white man could still rock a picked-out fro (and a balding one at that) to this day.

Forget the leather vests. Forget the skull-emblazoned muscle tees. Forget the leopard-print everything. All of those can be chalked up to the fact that it was the '90s. But this man is STILL wearing the damn bandannas — like they're surgically attached to his hairline — even when he wears a suit. There's “branding” yourself… and then there's looking skankier than the women you date on TV.

Sure, Wayne earned himself a spot on our list of most stylish celebrities of 2011, but we can't deny that he's made some pretty serious style offenses. Congrats Weezy, you are officially the best/worst-dressed celebrity. The word “jeggings” is a terrifying concept in general, exponentially so when in reference to a nearly 30-year-old male's signature style. Add a skintight sag on that shit, and you've got a horrible example being set for the youth of America (we're looking at you, Justin Bieber).

Let's get one thing straight, without Jordan there would be no sneaker game. And we worship the ground he walks in his signature shoes. But it's the mock-turtleneck collection (rivaling only that of Steve Jobs) where Jordan gets into some serious sartorial shit. What happened? When he was still playing he killed it in a suit. Somebody needs to tell Money to stick with Jordan Brand.

The bow ties and the taped plastic glasses were adorable when Chris Brown was still the kid blowing our shit away with his MJ-esque moves at the 2007 VMAs. But a handful of years, a national domestic-abuse scandal and a platty dye-job later, he just comes across as desperate for attention. Shockingly.

He loses points for blatantly biting Elton John's feathers-and-sunglasses “Crocodile Rock” costume. He gets points for always looking like he's having a good time in those crazy outfits. He loses points for looking like a sack of WTF compared to Adam Levine on The Voice. He gets sympathy points for having to sit next to Christina Aguilera on The Voice.

With his perpetual full face of ladies' foundation and a bouffant that may as well have birthed Amy Winehouse herself, Little Richard just narrowly made it on this list — mostly because his status of "male" is still yet to be determined.

If Kevin Smith's “clothing” — is that a bathrobe? — could talk, it would say “I give up.” Just because you're not built like, say, Hugh Jackman, doesn't mean you should put as little effort as possible in your wardrobe. Buddy, you have options! START WITH CLOTHES THAT FIT. Invest in pants that cover up your cankles. Or, if you really want to look good, simply lose half of your body weight, a la Jonah Hill.

On a list rife with repeat bowling-shirt offenders, there is no question of who the undisputed king is. The man literally created a primetime sitcom character based on an outfit composed of gross shirts, khaki cargo shorts, and Merrells with socks. But what might be worse is that he literally wears it off the set and throws on a flame-ribbon fedora for an cohesive day-to-night appeal. #FAILING.

There is no denying that Cosby is a cultural icon. And as much as we love a good "Cosby" sweater, the reality is that many of these knit abominations should have been left in the dressing room. It's too bad that for decades dads and grandpas have been under the impression that it's okay to wear them because of The Jell-O Man's co-sign. Props to Drake for keeping the trend alive in 2011; let's hope it dies in 2012.

If you were trying to break into an industry saturated with middle-aged women in head-to-toe Chico's, you'd go balls out with bowling shirts and platinum tips too, right? Anyone? No? Well, evidently it worked for Guy Fieri, who quickly climbed to the top of the Food Network ranks as one of its highest-rated hosts. But the real plot twist of this rags to… rags story, is an endorsement by the one and only TGI Fridays. Stereotyping will never not be fun.

You know it's bad when you see an actor dressed at Che Guevara and think, "Awww, he cleaned up." Seriously, with all those bad polos-under-blazers, faded khakis and foam ball caps, Benicio looks like he should have to notify the National Sex Offender Registry when he moves.

Women love a man in uniform — even a Yankees uniform. So what's the problem? During the months of the year he's not suited up, he's sporting seriously cheesy jackets. Let's be real, dude can obviously wear whatever he wants, because among the women who he has shared a bed with are Jessica Biel and Minka Kelly.

Universally adored by women since he swung a hair dryer in Thelma & Louise, Brad Pitt also has that unique “guy's guy” ability to convert any dude to an all-dry-chicken-breast diet (Tyler Durden for life). He does okay on the red carpet, but seriously, he must be so over being adored. That's why when left to his own devices (read: sans stylist), he ends up looking a little more Jesse James and a little less Joe Black. So when Brad goes all fedora-and-chin-pubes on us, we plug our ears and cover our eyes like that of the tantrums of his 47 children.

It's so hard to pick the worst offender in this bunch, but we might have to go with The Situation, who was publicly scolded by one of his favorite brands because they didn't want to be associated with him. And let's not forget that tuxedo line — probably for guys who don't mind going to prom alone. However, their collective affinity for rhinestoned Ed Hardy tees is another serious concern.

We get it: You love the environment and PETA and soy cheese. But you don't have to dress like an actual Peace Corps field worker to change the world, Moby. Maybe just stop making shitty trance/ambient knock-offs, and elevate your wardrobe beyond a barrage of sarcastically worded tees.

We're not mad at "Welcome to the Jungle"-era Axl. That dude was a rock star. But fast forward, and like Bret Michaels, Axl Rose has a severe aversion to showing his forehead in public. Extra-wide bandannas, backward hats, and even feathered bangs have all graced the top part of his head... and when he finally bared all, we realized why: he is a grown white man with cornrows.

Listen, Adam. We are excited for you. You came in (gasp) second, one season out of ten, of a reality-television sweatshop that churns out success stories of the likes of Ruben Studdard, Taylor Hicks and David Cook. How do you handle the pressures of marginal suburban fame? What ever will you do to continue whoring for attention? Oh right, by pruning your reverse mullet (promotional consideration provided by Kate GoslingTM).

Look, we're not picking on this tie-dye-haired NBA hall-of-famer because he's a cross-dresser. We're picking on him because he's a TERRIBLE cross-dresser. That halter top with faded jeans and a belly chain? That dressy pink tank with warm-up pants? Well, at least he looked darling in his wedding dress.

The man that launched a thousand Hot Topic armies, Marilyn Manson takes goth cross-dressing to its outer limits. But now that the '00s and all their terrible pop-rock heroes are a thing of the past, we wait with baited breath for the androgyny poster child's next image move.

How can a human being have so much money and consistently look so shitty in public? Howard Stern is the self-proclaimed King of ALL Media — not just the radio variety, where it's okay to wear, say, the saddest, saggiest cargo sweatpants in existence.

He may be over the clown makeup and teased tresses, but Dee Snider has moved into a more sophisticated look of a curly, greased ponytail and black shades, begging the classic chicken-or-the-egg question: who came first — Dee Snider or the Nickelback guy?

We suppose that if we were as chiseled as Matthew, we'd spend our days shirtless — and do a zillion cheesy shirtless movies — too. But it seems he's gotten so used to not getting dressed that when he must put together an outfit of actual clothing, he simply doesn't understand the concept. Which is a shame, because when he sets down his bongos and hires a stylist, he's the coolest stoner on the red carpet.

Thought old Hef only wore his satin PJs in public? Don't count out his second favorite look — the navy blazer and yachting hat (you know, for casual sporting outings where a smoking jacket is just a faux paus) — keeping the Gilligan's Island motif totally relevant and current for the 21st century.

With his lifetime supply of awful hats, dirty wife beaters, and the occasional pimptastic hoodie, Kid Rock's “American badass” schtick is giving American style a bad name. We'd much prefer the USA to be identified with, say, Bruce Springsteen's Levi's 501s and crisp white tees... and, if we want to paint a truly honest American picture, maybe a pack of Marlboros rolled up in the sleeve.

Tracy Morgan's inclusion on this list is equal parts due to his uniform of embossed leather jackets and his preferred red carpet pose we like to call "Nipples Gone Wild." Sure, it's our collection of the worst-dressed celebs, but for this special case, we're adding in undressed bellybutton stretch marks into the nominating equation.

As that chick on Gossip Girl once proclaimed, leggings are not pants. Which means neither are pleather leggings, or jeggings, or anything else that ends in “-eggings” that men shouldn't even be wearing to begin with. But some dudes will wear them anyway. Fine — maybe it's a British thing. In that case, you know what you DON'T pair with skintight non-pants? An uber-deep V-neck that shows off your décolletage.

T-Pain's commitment to top hats is, frankly, impressive — considering he actually had to look at himself in 332 of them for the better part of two years. But he went on the record in 2010 to say he had given them up. “That was just for the Thr33 Ringz album just for a ringleader look,” he told Carson Daly. “I figured if I'm gonna be fat with dreads, I might as well wear stupid clothes too.” Wow. So these were part of a carefully constructed, strategic marketing campaign? Visionary, T-Pain, absolutely visionary.

So this guy used to be the quirkily-dressed-but-still-lovable goof. Now he's just the sad, sweaty middle-aged man who considers it a good night if it involves suspenders and a midget. Which makes us reevaluate all the weird shit he's worn that we found endearing at the time...

Vests with bare chests, a closet full of electric-colored snakeskin, an omnipresent topknot — as questionable as his sartorially choices might be, we can't help but hold out a slight hope that someday Mickey Rourke is going to bust in an event in full-on Mortal Kombat regalia. And that, my friends, would be excusable (and fucking awesome). However, in its potential interim, we will continue to gape at the absurd descent anyone can plummet from 9 ½ Weeks to 9 ½ chihuahuas.

With his fresh neons, windbreakers and sneakers tucked safely away in the '90s, Will's wardrobe for this millennium — excuse us, Willennium — has been relatively sharp. Well, with a few notable exceptions. Unfortunately, something comes over him whenever it's time to make a music video. For every dapper suit at a premiere, there's a puffy adidas tracksuit (“Gettin' Jiggy Wit It”), what appears to be a fake janitor's uniform (“Switch”), or, most concerning, a cowboy-turned-pimp costume (“Wild Wild West”), which was distracting even next to Sisqo.

“Oh my god! We're club kids! Trustfund cokeheads from Miami love us! Schizophrenic neon and/or animal prints will get us on MTV! Ironic fake glasses! Shots! We'll be relevant forever!” — hypothetical but plausible internal monologue from every delusional flash-in-the-pan ever. However, we are pretty damn excited for the inevitable resurgence of this Google search in 30 years.

Think back to the early 2000s, when John Mayer was only slightly annoying, turned seemingly every single into a hit, and dated a steady stream of famous Jennifers and Jessicas. Then he started flaunting his physique in attention-grabby costumes and spouting misogynistic rants; more recently, he resurfaced as a scummy Johnny Depp knockoff spouting racist rants. Not a Lindsay Lohan-level waste of potential, but dude kind of blew it.

Trucker hats. He gave us fucking trucker hats. We will never be able to forget that, and it's only being made worse by shifting gears to this new, perpetually shirtless-Jesus motif (made possible by the ratings whores that bring you Two and a Half Men). So now begs the question: what obnoxious trend will Ashton Kutcher be responsible for next? Fur man-vests?

It takes a lot to come full-circle in this crazy world we call Hollywood, especially when you go from a muscle tank and a mullet... to a muscle tank and a SOCCER-MOM bob. But don't go thinking Billy Ray is a simple fellow. He didn't just jump from just Point A to Point B — he's had pit-stops at flat irons, feathered bangs and (shudder) soul patches to keep him in the inner circle of the unfortunately groomed.

Not everyone can lay claim to having a historical pant named after them. But thank god he had those infamous drop-crotch gold lamé numbers (complemented by cropped blazers and oversized chains) to deter from that pesky tax evasion situation. Otherwise, we would have lost all respect.

We started to make some lame joke about how Blade here should be serving time for his horrific style instead of tax evasion… but that pinstripe atrocity is killing out vibe, and we can't muster any snark right now.

How awful is will.i.am's closetful of shiny, costumey outfits? Well, fellow Black Eyed Pea Fergie looked less ridiculous when she peed her pants onstage.

Lil Jon's got plenty to clown on. None of his clothes ever fit. He's always wearing bad sunglasses and a stupid crown. He looks like a cross between a cracked-out pimp, a court jester and one of the kids from Kriss Kross. But his worst offense: wearing bling with jorts. Bling goes with literally every imaginable item of clothing except jorts.

To launch a four billion-dollar film franchise from the creative basis of… a waterslide… everything has to be on point, especially the believability of your foppish, swashbuckling leading man. Thank God, Disney had the foresight a decade ago to tap Johnny Depp — a grown man who already on his own accord can somehow wear five shirt and three scarves, and you can still see his chest.

Steve Harvey is pretty damn presumptuous. He wrote Act Like a Lady, Think Like a Man, assuming that women want his dating advice (side note: he's been married three times). And he hawks his own line of men's suits — The Steve Harvey Collection, natch — assuming that dudes admire his goofy getups. Another side note: the brand's tagline is “Enhance Your Swagger”. More like "Enhance your collection of ill-fitting suits and bad ties."

For a man who hasn't strayed from hockey jerseys and sweatpants publicly since 1994, he gets some credit for consistency. That's why he's #2 and not #1. We get it, he's the funnyman who makes a fashion statement by making an anti-fashion statement, but when you're worth $300 million, one would think you'd bother to invest in a proper suit, maybe if only for the red carpet. But hey, the guy made Jack and Jill, so his quotient for giving a fuck is evidently sub-par.

Ugh, Jared Leto. Another celeb who has the resources to look amazing yet refuses. So what catapults him ahead of the 49 other fools on this list (besides his skeazy photo shoots with Terry Richardson)? The amount of painstaking sartorial effort he exerts to look like a complete idiot — you can practically hear him thinking, “Do my red sneaks go with these drop-crotch silk pants? Does this mesh tank top make my nipples look weird?” He's basically a real-life Derek Zoolander: He honestly believes he's a fashion god, while everyone snickers behind his back. Next time he's sitting front row at YSL in his expensive man-dress or studded capris or whatever, we hope he has an epiphany and echoes our thoughts out loud: “Ugh, Jared Leto.”