The 50 Most Stylish Fat Guys of All Time

Image via Complex Original

Occupation: Musician

Approximate Weight: 200+ lbs.

Although his time on the planet was brief, the trumpeter made a profound impact on the jazz world. As such, he was regularly decked out in some pretty great suits and tucked in shirts. Yes, it was the '40s and just the norm, but you can't say he would look out of place in the context of today's stylish guys either. Whether tooting his horn in untucked button down shirts or looser, double-breasted suits, Fats Navarro certainly looked good doing his thing.

Occupation: Rapper

Approximate Weight: 460 lbs. (at fattest)

The diehard Knicks fan has shed a few pounds for sure, bringing a literal sense to his song "Drop A Body," but while his poundage may have lessened, his style sure hasn't. Street to his core, you'll often find him rocking an array of straight-billed caps, and he's been spotted rocking sunglasses indoors on numerous occasions. You also can't touch his array of iced-out accessories. From big-faced watches to the ill "Terror Squad" chain, Fat Joe stays shining.

Occupation: Actor

Approximate Weight: 300+ lbs.

Hopkins had a role in Lean On Me, but his claim to fame wash his role as "Steel" in Juice. He was just so damn fresh with that flat top and even made overalls look good. This scene of him dancing in a mirror just contains so much swag and awesomeness—easily cementing his spot on this list.

Occupation: Comedian

Approximate Weight: 200+ lbs.

Friedlander always dresses like he just woke up in Williamsburg, Brooklyn and showed up to your party uninvited. And we can't fault him for it. At least the guy is consistent, knows what works for him, and actually doesn't look half-bad. His array of cheeky trucker hats, thick-rimmed square glasses, and "World Champion" T-shirts are simple, but also comprise his signature style. Good on him for occasionally throwing a denim jacket or coaches jacket over it all for variety's sake, but his dedication to his personal steez is worthy of some sort of "perfect attendance" award—it's always there.

Occupation: Actor

Approximate Weight: 250+ lbs.

Anthony Anderson may have got his start as a second banana, but his style is definitely worthy of leading man status. What he does well is wear things that complement his body type. Not too baggy, not too tight, just right. That's why suits look especially good on him, and his casual gear (down jackets, unbuttoned shirts) doesn't hang off his body. Hell, he can even wear tacky golf clothes and miraculously pull them off—he knows how to balance out crazy prints with solid colors.

Occupation: Comedian

Approximate Weight: 300+ lbs.

Before Jason Alexander was inadvertently setting trends as George Costanza, John Candy was already rotating a wardrobe of reliable menswear staples. Sure, it wasn't mind-blowing fashion, but it looked good, worked, and wouldn't look out of place today. He especially shined when he rocked a fedora, topcoat, and scarf. Oh, and that whole patterned shirt buttoned all the way up with no tie under a sportcoat look? Yeah, he started it.

Occupation: Fashion Designer

Approximate Weight: 300+ lbs.

Belgian designer Beirendonck is revered as one of the "Antwerp Six," six graduates from Antwerp's Royal Academy of Fine Arts who would greatly influence the fashion industry. It's an honor he shares with other lauded designers like Dries Van Noten and Ann Demeulemeester. While Beirendonck's own designs favor prints, knits, and avant-garde scarves that have developed their own following, he is known for his own sense of style as well. Though he's bald, he maintains a pretty great beard, and is a master of rocking multiple rings. What he also does well is pair bright colors with an otherwise subdued palette, like a seafoam blazer or red shoes.

Occupation: Comedian

Approximate Weight: 296 lbs.

Chris Farley's disheveled style channeled John Candy's classic, put-together menswear looks and infused them with a frat-like, party boy sensibility. You'd nary find him suited up, opting for open buttons and printed Hawaiian shirts under suit jackets instead. And if he did wear a tie, you bet it hung low rather than stay knotted up. There was always a dash of unkempt sprezzatura to Farley's kits, and we remember him fondly for that, as well as his hilarious body of work.

Occupation: Actor

Approximate Weight: 218 lbs.

Orson Welles could rock a suit with the best of them, but where he really shined was his ability to grow and maintain a pretty amazing beard. For a guy who got his start in the radio industry, his look wasn't half bad. Even after he piled on the pounds, he never looked like a slob.

Occupation: Comedian

Approximate Weight: 280 lbs.

Hardy, of "Laurel and Hardy" fame, was easily recognized not just for his rotund shape, but his dedication to the bowler hat. Perfectly accessorized with a Chaplin-esque Toothbrush mustache, he was also pretty put together in a suit. When you think about how many slapstick scenes his clothing had to endure, you can almost imagine how durable his outfits had to be. He also made a case for rocking a wider necktie everywhere—not only did it serve to separate him from the usually-bowtied Laurel, it no doubt accentuated his rather wide neckline.

Occupation: Artist

Approximate Weight: 280 lbs.

Artist and political activist Ai Weiwei has an understated style that works for him. Consisting mostly of dark colors—especially black, the silhouettes are simple and everything fits pretty great. It's bohemian without being poseurish, and not the least bit costumey. It's very utilitarian without channeling any allusions to Chairman Mao, and his facial hair is unkempt enough to make him look like a creative type while not making him look homeless.

Occupation: Comedian

Approximate Weight: 500+ lbs.

Most of Lavell Crawford's comedic material riffs on the fact that he's a fat dude. That said, you can't deny he knows how to wear it well underneath an assortment of pretty good suits. While he certainly looks good in navy blue and brown tweed sport coats, he really shines when he embraces animal prints, like snakeskin waistcoats as part of a suit. Plus, he looks like a real-life version of The Kingpin from Spider-Man.

Occupation: Baseball Player

Approximate Weight: 215 lbs.

Obviously able to rock baseball gear on the same level that most rappers do today, it's pretty safe to say that The Great Bambino made the Yankee hat more famous than well, anyone else. When he wasn't setting records for career home runs, he was as well dressed as most of the dudes on "Boardwalk Empire." Underneath his cap lay a well-coiffed plume of slicked-back hair that wouldn't look out of place at today's throwback barber shops, and when called upon to dressed to the nines, he also knocked that out of the park.

Occupation: Musician

Approximate Weight: 300+ lbs.

R&B crooner Levert was every bit a big-bodied heartthrob for many women. When he called himself "Mr. Too Damn Good" he wasn't lying. He kept it fresh in '90s staples like suede jackets, sunglasses, and fedoras, but also knew how to rock timeless pieces like bomber jackets and chunky knits. He was also no stranger to a pair of thick-rimmed glasses and a solid gold chain that showed people you had street cred without looking like a victim of the bling era.

Occupation: Wrestler

Approximate Weight: 520 lbs.

In the ring, he was a towering man in a solid black leotard. Outside of it, he was actually pretty dope. In addition to the frizzy hair and amazing sideburns, Andre The Giant would absolutely kill it when it came to casual gear. We're talking houndstooth sportcoats, ill Hawaiian shirts, and even floral shirts. Dude was rocking menswear trends before plenty of today's trendsetters. No wonder Shepard Fairey says he had a posse!

Occupation: Music CEO

Approximate Weight: 265 lbs.

Act like Suge Knight's imposing figure wouldn't scare the shit out of you. At 6'2, we can easily see why he could intimidate many people, especially Vanilla Ice. He complemented his menacing stature with a primarily red wardrobe, no doubt where some of the allusions to his associations with the Mob Piru were construed from. Besides that, he looked really fresh, and when posed next to Death Row Records artists, you could easily tell who was the boss. He does know how to incorporate a little variety into his wardrobe, mixing in buttery leather jackets and casual plaid shirts, but always sure to accessorize with a mean chain, ring, and cigar.

Occupation: Comedian

Approximate Weight: 400+ lbs.

Yes, Bruce Bruce can certainly pull off a plus-sized suit, but the comedian really goes the extra mile with some pretty choice hairdos. Bruce Bruce's curls are a force to be reckoned with, and he regularly rocks them with dapper accessories like printed ties and pocket squares.

Occupation: Musician

Approximate Weight: 299.8 lbs.

Fats Waller had an iconic smile, but he was also known for the half-ashed cigarette partially dangling out of it. He essentially created Guns N' Roses guitarist Slash's signature look years before he was born. Like most jazz musicians, Waller was almost always suited up—those were just the times. But where he injected his own personality was with a rounded bowler hat and pencil mustache.

Occupation: Drug Lord

Approximate Weight: 200+ lbs.

Even though he's regarded as a hero in some parts of Colombia, when you think of every other eccentric, well-dressed villain in action movies, chances are they're channelling Pablo Escobar. The light suits, straw fedoras, oxford and Hawaiian shirts? That's pretty much sartorial par for the course for the drug lord. His style may not have been as precise as Gadaffi's despot swag, but it still holds up on its own over time.

Occupation: Actor

Approximate Weight: 250+ lbs.

While Gleason achieved fame playing a blue-collar bus driver on "The Honeymooners," when he was off-camera, his style was pretty high class. Regularly decked out in tailored suits, ties, and a great classic haircut, he rocked pocket squares and lapel flowers with the best of them. The latter became a bit of a style signature, as he wore a flower in his lapel throughout most of his life.

Occupation: Fashion Designers

Approximate Weight: 1000+ lbs. (combined)

The Costello Tagliapietra co-designers are staunch supporters of the personal uniform, which is why they pretty much wear variations of the same thing all the time. Granted, they both could pass for ice road truckers or Canadian lumberjacks, what with their devotion to flannel, huge beards, and suspenders, but you know what? It works amazingly for them both. They've bought numerous pairs of fancy Italian trousers from Incotex and racked up on a bunch of vintage Pendleton gear in order to make sure their supply of urban woodsman gear is never short. Who cares if they cut patterns more than they chop trees? When your kits regularly channel this much swag, you get a pass.

Occupation: News Anchor

Approximate Weight: 200+ lbs.

Roker's weight problem may have been hazardous to his health, but since dropping 140 pounds his style has certainly gotten better. Whether it's tailored suits, comfortable knits, or topcoats with a fedora, he's poised to give Matt Lauer a run for his money as The Today Show's best-dressed dude. Hell, even when he's on the scene reporting about the weather, his outerwear game remains on point—we're talking yellow slickers in the rain and Canada Goose jackets on especially blustery days.

Occupation: Comedian

Approximate Weight: 250+ lbs.

Cedric The Entertainer probably has the largest hat collection in the world. He is never seen without one, it's his trademark. Granted, it might be because without his hat, he kind of resembles a headwear alive, and continuing to show guys that fitteds, beanies, and snapbacks aren't your only options.

Occupation: Rapper

Approximate Weight: 255 lbs.

Biz Markie has always looked cool. Whether rocking a hat with his name on it in iron-on Cooper typeface (decades before OFWGKTA had co-opted the font for its merch), or wearing a camo parka, he kills it on the regular. The fat chains, Champion sweatshirts, and quilted jackets he rocked in the '80s were beyond dope. It's tough to look good, but when your style can hold its own against Big Daddy Kane, one of the GOATs, it's safe to say you're doing it right.

Occupation: Comedian

Approximate Weight: 200+ lbs.

The heavier half of Abbott and Costello was often portrayed as a chubby, bumbling guy, but his style couldn't have been more on point. Often seen in patterned jackets like gingham, houndstooth, and pinstripes, his bold sportcoats were supposed to serve as a gaudy foil to Bud Abbott's conservative straight man, but actually ended up making Costello look like he was the stylish guy while Abbott was boring menswear nerd.

Occupation: Boxer

Approximate Weight: 260 lbs.

How regal did Foreman look in his prime? With that jacket draped around his arms, gloves hanging next to his shorts, he looked like a king about to hold court. As he grew older, he adopted some basic wardrobe staples without ever looking too much like an old dad, still looking like a champion in three-button suits, checkered scarves, and even managing to pull off a newsboy cap.

Occupation: Rapper

Approximate Weight: 350+ lbs.

Action Bronson dresses like the streetwear dude that hangs out at the shop and always wears the freshest pieces, fucks the illest chicks, and smokes the best weed—and you wonder how he does it. Whether decked out in Diamond Supply or denim vests, there's a decidedly hood aspect to how he dresses himself. The opposite of most heavy dudes who try to keep it classy in suits and look good because of it, Bronson just throws a heavyset middle-finger-to-the-world and rocks hoodies, snapbacks, and T-shirts like a champ. The Queens foodie just pulls it all off with pure aplomb. He has no fucks to give, as he says in "Bird On A Wire," you could catch him rocking shorts in the winter.

Occupation: Comedian

Approximate Weight: 350+ lbs.

For a guy who complained about getting no respect, he sure deserved it for his sense of style. Dangerfield wasn't afraid of going bold or cavorting around in shorts and boxers. While he looked good in a suit, he was known for looking kind of stressed, always with the top button undone and a loosened tie. In his later years, he might care less, but he still looks unintentionally cool. Only he could rock a khaki jacket, shorts, and loafers on the red carpet but keep it together with a Barneys bag as an accessory.

Occupation: Actor

Approximate Weight: 300+ lbs.

Looking like a modern day version of William Howard Taft, Wilford Brimley comes off as a cantankerous, heavyset older guy. That might be because of his numerous Liberty Medical commercials where he talks about his struggles with diabetes—or as he pronounces it: "die-a-beet-us." We can't think of any other man that can pull off a handlebar mustache as well as he does. And when your co-star is none other than Chuck Norris, and you're able to hold your own, that speaks volumes about how badass you are. His round-framed wire glasses are as vital to his look as his mustache, and he looks pretty great in a cowboy hat or even a casual fedora.

Occupation: Actor

Approximate Weight: 300+ lbs.

When it comes to fat guys with swag, Marlon Brando is a definite shoo-in. He's the fucking godfather, literally. But besides getting dappered up to be Don Corleone, he set an example for former Hollywood heartthrobs who also didn't age as gracefully. Look at guys like Jack Nicholson and Alec Baldwin, who've put on a few pounds in their twilight years. Brando stuck mostly to staples like dark suits and golf jackets, and sure, sometimes he even went casual with denim jackets and printed shirts, but when it came time to be in the spotlight or on camera, he knew how to dress for his body type.

Occupation: King

Approximate Weight: 200 lbs.

The man who separated church and state—and was known for multiple marriages—was like the original celebrity scandal. His pride and personal vanity is why he strived to make a male heir, but it also resulted in some pretty exquisite looking garb. While no photos exist, he certainly looks like a boss in all his portraits. Leggings aside, his regal fur and patterned garments look luxurious as hell, and he was also known for wearing a noble "cap of maintenance"—often made from velvet and lined in ermine (that's short-tailed weasel for you peasants). To top it off, with that facial hair, he looks like Action Bronson's ancestor.

Occupation: Musician

Approximate Weight: 260 lbs.

With a steady diet of peanut butter, banana, and bacon sandwiches, Elvis noticeably put on a lot of weight in his later years. While his earlier days consisted of well-fitting menswear staples, his heavyset twilight years were characterized by studded leather suits. Who will ever forget the primarily dark get-up he rocked when meeting then-President Richard Nixon? Aside from the dark coat draped over his shoulders, what was really noticeable was the fact that he seemed to be wearing some sort of professional wrestling championship belt.

Occupation: Rapper

Approximate Weight: 698 lbs.

He wasn't a player—he just crushed it a lot. No really, Big Pun outfreshed even the freshest on the regular. Regularly seen in boss gear like velour suits and silk shirts, he wasn't afraid to keep it real in a chore jacket and Timberland boots either. He could accessorize like a champ too, often rocking baseball caps, bucket hats, and the occasional du-rag. His style is missed almost as much as his presence on the mic.

Occupation: Director

Approximate Weight: 300+ lbs.

The great director dressed to impress. At the time, Hollywood was all about suits—and man could he pull one off. The corpulent filmmaker was known for his dark suits, bald head, and overweight silhouette. One of the first auteurs—a man who stressed complete creative control over everything, it would then make sense that he'd have a good vision for his behind-the-camera aesthetics as well as what gets shown on screen.

Occupation: Fashion Designer

Approximate Weight: 222 lbs. (when fat)

Karl Lagerfeld dropped 90 lbs. putting him around 132 lbs. these days, but while his weight has fluctuated, his signature look hasn't. The Chanel creative director has always been known for his oversized sunglasses and shock-white ponytail. His personal uniform has always been a variation of the suit and tie look, with the width of the tie changing with trends, incorporating materials like leather and details like studs into his kits. He's added black gloves to his uniform since slimming down, but in his heftier days he was spotted carrying a folding fan.

Occupation: Rapper

Approximate Weight: 344 lbs.

Heavy D is the original fat rapper. Biggie Smalls? Big Pun? He was there before both of them. Rocking sunglasses and track suits like a champ, the overweight lover was easily the best dressed out of "Heavy D and The Boyz." He always sought to set himself apart style-wise, whether it was yellow track suits with a matching bucket hat, or an all-red suit (way before Suge Knight) and polka dot necktie.

Occupation: President

Approximate Weight: 320 lbs.

The 27th President of the United States was a very, very, steezy Republican. Besides his formidable handlebar mustache and sheer girth, he looked awesome in pretty much every photo. Even though it's been said he got stuck in the White House bathtub, you really can't stay mad at a guy who can wear a porkpie hat and petticoat like a real boss.

Occupation: Comedian

Approximate Weight: 230 lbs.

All hail the crewneck sweater king. While he became immortal as Bluto in Animal House, rocking a sweatshirt with "COLLEGE" emblazoned on it over a button down and plaid pants, people also remember him as a suited-up Blues Brother. The well-rounded funnyman was an integral member of the original Saturday Night Live cast, and actually looked pretty damn good. His secret? Sticking to menswear basics. Belushi proved early on that any guy can rock plaid shirts, bomber jackets, and simple knits.

Occupation: Fashion Designer

Approximate Weight: 200+ lbs.

The diminutive creative director of Lanvin is known for his uniform of thick-rimmed glasses, a dark suit, white shirt and a bow tie. Sometimes he switches up the neckwear with a scarf, but his wide, big bow ties really shine. He also is a staunch supporter of the one-button jacket, which actually accentuates his short, stout frame. He's a fashionable version of Batman villain The Penguin.

Occupation: Rapper

Approximate Weight: 310 lbs.

The bawse is no stranger to looking like one. Whether in streetwear brands like DGK, or silk Versace shirts, he knows a thing or two about style. That also extends to his iconic accessories, like the Cazal sunglasses that regularly frame his face, or his easily-spotted self-portrait chain. His kick game is on-point too. Sure, he has a deal with Reebok, but that doesn't stop him from stunting in high-end sneakers from Louboutin. "They recognize me by the red bottoms I wear" indeed.

Occupation: Comedian

Approximate Weight: 242.5 lbs.

Funnyman Zach Galifianakis really cleans up well, but knows how to keep things casual. What's ironic is that when left to his own whims, he often ends up looking better than the slobby costumes a lot of his characters have to wear. He also tends to keep up with his menswear trends, whether it's fair isle sweaters, dirty buck suede shoes, or even rocking New Balance sneakers with tailored gear. His biopic would probably be called "My Big Fat Greek Style Icon."

Occupation: Comedian

Approximate Weight: 300+ lbs.

Patrice O'Neal was hilarious, but never looked as funny as he was. His style was actually very similar to how rappers dress, consisting of a lot of baseball caps and leather jackets. His cap game was really on point though, ranging from patchwork suede, elephant print, and even Coogi. You can't deny that dude had taste. When he wasn't rocking an all-black outfit that would make Jay-Z jealous, he dressed up in gear like velvet or leather blazers and a simple fedora. It was clean and timeless.

Occupation: Prime Minister

Approximate Weight: 250+ lbs.

The British Bulldog had a wardrobe as serious as his love for alcohol. Even in the midst of wartime, he kept it fresh in an assortment of three-piece suits, pocket watches, bowler hats, and outerwear like double-breasted topcoats. He was every bit as dapper as a leader of his stature should have been, often photographed in a signature polka dot bow tie. If a heavier guy wants a style icon to model himself after, Churchill is a great one to aspire to.

Occupation: Musician

Approximate Weight: 350+ lbs.

The legendary Italian tenor could rock a tuxedo with the best of them, but even his casual outfits dripped with luxury and class. An adamant scarf wearer, he'd often rock colorful ones around his rather large neck, either draped with the proper amount of Italian sprezzatura, or tied just so to make him look more classy. You can't fault his headwear game either, often seen in fedoras and newsboy caps, but definitely looking more like a gentleman than a hipster. If you posted his photo on tumblr, people might mistake him for a street style maven rather than one of the greatest musical voices of our time.

Occupation: Comedian

Approximate Weight: 250 lbs.

This loudmouthed funnyman was known for a) being extremely politically incorrect and b) looking like a plump Axel Rose. Whether it was a saggy beanie, beret, or many of his bandanas, Kinison's look was as anti-establishment as his material. He dressed half like a pirate, and half like a Beastie Boy. It was a boisterous style that went perfectly with his ribald humor. Not only was Kinison regularly screaming into the mic, but his loud steez helped cement his status as an icon.

Occupation: Musician

Approximate Weight: 245 lbs.

Fats Domino's flat-top was simply ahead of its time. In the '50s, it was entirely his own. It would take about 30 years for it to be adopted as a trend among black youth. Given the context of the flat-top's popularity in the late '80s and early '90s, it's really dope to see it juxtaposed with a proper suit and Domino's slick demeanor. Plus, even though he was a fat guy, all of his suits were expertly tailored and he wasn't afraid to rock things like a skinny tie, tie bar, and spectator shoes. In fact, the cover to 1957's Here Stands Fats Domino looks like a direct precursor to Kanye West's Rosewood Movement.

Occupation: Musician

Approximate Weight: 200+ lbs.

Dungeon Family's other big boy often lets his freak flag fly. That doesn't mean he has no idea how to dress up, but there's no denying that his sense of style is nothing short of adventurous. He's rocked studded leather jackets, bright shiny suits, and even apocalypse-worthy armor during his stint as a judge on "The Voice," and his career is full of even more awesome outfits like sequined sweaters. That isn't to say he doesn't know how to tone things down. He looks just as good in a suit or motorcycle jacket and beanie. He can keep it real and fashion-forward, because he's that confident in himself and his taste.

Occupation: Gangster

Approximate Weight: 250 lbs.

From Nucky Thompson to The Notorious B.I.G., every gangster has learned from this boss. Looking every bit as intimidating as he should, he dressed to the nines and carried a nine as well. His hats were on point, topcoats luxurious (with a scarf worn underneath, natch), and even his mugshot drips with aspirational style. For every guy that dreams of dressing like a bona fide G, Al Capone is the style archetype.

Occupation: Editor

Approximate Weight: 300+ lbs.

Meet the man who puts the "at large" in "Editor-At-Large." You don't become Anna Wintour's right-hand-man without being undeniably stylish, and André Leon Talley is the walking epitome of aspirational style in every aspect of his life. Name another person who unabashedly plays tennis in Louis Vuitton. This North Carolinian hustled his way into fashion by way of his first gig with Andy Warhol, and has been making shit happen ever since. Even though he's dropped a couple of pounds because Oprah convinced him to, he advised Michelle Obama on her fashion choices in 2008, introducing her to designer Jason Wu, who went on to put her in the gown she wore on her husband's inauguration night. Forget Kanye, if you talk about style around this guy he'll more than embarrass you—in fluent French.

Occupation: Rapper

Approximate Weight: 395 lbs.

Beyond the red and black lumberjack with the hat to match, The Notorious B.I.G. was a sartorial force to be reckoned with. Hands down one of the most stylish rappers of all time, he knew what worked for him and also how to upgrade his style without sacrificing his street cred. He looked every bit a viable thug whether throwing dice in a flannel shirt and Timberlands, or decked out in a custom white suit and hat. From the Coogi sweaters, topcoats, and ever-present canes, there's no doubt that his style reigns eternal for portly gentleman everywhere.