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The best (and worst) signature looks of celebrities
Michael Ochs Archives/Getty Images

The best (and worst) signature looks of celebrities

There are plenty of celebrities in the world of Hollywood, music and fashion, but not many of them are associated closely with a certain look. That can be great if you're a cool actor like James Dean and can be disastrous if you're an uncool chef like Guy Fieri. Some looks stand the test of time, like Elton John's jackets, while others are terrible in any era, like MC Hammer's pants. For every fashion icon there's a fashion victim, and this list will deliver a healthy portion of each, as we serve as fashion police, judge and jury.

 
1 of 25

Best: James Dean

Best: James Dean
Photo by Keystone/Getty Images

James Dean's style was simple, yet completely iconic: plain white T-shirt, blue jeans, leather jacket and of course, his quiff-like hair. He also single-handedly made chunky turtlenecks popular. Dean died at age 24, which makes his look even more timeless — he didn’t live long enough to make terrible fashion choices in the '60s.

 
2 of 25

Worst: Guy Fieri

Worst: Guy Fieri
Photo by Christopher Polk/Getty Images for Maxim

It completely makes sense that to stand out in the well-populated field of celebrity chefs, Guy Fieri would embrace a thoroughly distinctive look: bleached blonde hair with frosted tips, elaborately shaped goatees, bowling shirts covered in flames and sunglasses that are often worn backward. That still doesn’t make it a good look. Fieri somehow looks like his clothes were overseasoned — as if Donkey Sauce had become a shirt — but perhaps that’s the mandatory dress code in Flavor Town. 

 
3 of 25

Best: Mr. T

Best: Mr. T

Pity the fool who thinks Mr. T wears a mohawk. T says that his signature haircut was inspired by photos of Mandinka tribesmen that he saw in National Geographic. T’s other signature look is his many bracelets and gold chains, which started back in his bouncer days when he’d prominently wear jewelry that was lost or left behind by someone he’d ejected from the premises. Mr. T stopped wearing gold after helping out in the aftermath of Hurricane Katrina, but if you suggest a new hairstyle, you are a fool and will be pitied as such.

 
4 of 25

Worst: Chris "Mac Daddy" Kelly, Kriss Kross

Worst: Chris "Mac Daddy" Kelly, Kriss Kross
Photo by Jeff Kravitz/FilmMagic, Inc

Can you blame the '90s for Kriss Kross wearing their clothes the wrong way? Only if you stop doing it before the '90s are over. In 2013, one half of the duo, Chris “Mac Daddy” Kelly claimed that he had been exclusively wearing his pants backward for 21 years. He says he was the first person in and will be the last person out on this fashion trend, so presumably Daddy Mac wears his clothes forward now.

 
5 of 25

Best: Elaine Stritch

Best: Elaine Stritch
Photo by Ron Galella/WireImage

It’s hard to say if Elaine Stritch was more of a legend on Broadway, on television or in the glasses aisle. She loved oversized frames and was far ahead of her time in that respect. Our hipsters would have had far smaller sunglasses, and Warby Parker would have had far less business had Strich not been such a trendsetter. 

 
6 of 25

Worst: Johnny Depp

Worst: Johnny Depp
Photo by Thomas Lohnes/Getty Images

Coco Chanel's famous advice for fashion was, "before you leave the house, look in the mirror and take one thing off.” Johnny Depp looks in the mirror before leaving the house and puts seven more things on. A hat, a scarf, two or three necklaces, tinted glasses and three or four rings. Sometimes he'll also ruin his facial hair! Depp has had periods where he'll start dressing like his movie characters, namely Captain Jack Sparrow or Hunter S. Thompson, but through it all the constants are bad hats and way too much jewelry.

 
7 of 25

Best: Young Michael Jordan

Best: Young Michael Jordan
Photo by Paul Natkin/Getty Images

When Michael Jordan came into the NBA, his Nike deal and subsequent Air Jordan campaign changed basketball and the sneaker industry irrevocably. Similarly, his clean, shaved head look essentially ended the era of balding NBA players. It must have driven skinheads crazy. And because Jordan always wore his North Carolina shorts under his uniform during games, he adopted baggier shorts and single-handedly killed the short shorts era. 

 
8 of 25

Worst: Old Michael Jordan

Worst: Old Michael Jordan
Photo by Johnny Nunez/WireImage

The sleek, influential looks of Young MJ have faded, and Old MJ has taken over. His signature look is to wear everything extremely wide and long. His jackets often go down to his knees, while his pants have the widest legs imaginable. You’ve heard of boot-cut jeans? MJ wears Das Boot-cut jeans, because you could fit a submarine into each leg. There’s an entire Tumblr devoted to his bad fashion choices: What the F*** Is Michael Jordan Wearing?

 
9 of 25

Best: Audrey Hepburn

Best: Audrey Hepburn

While Audrey Hepburn could wear the hell out of a pair of gloves, a black turtleneck and some cropped trousers, it’s the Givenchy dress she wears in “Breakfast At Tiffany’s” that remains most memorable. The “little black dress” became a necessary wardrobe piece, worn by women everywhere, including First Lady Jackie Kennedy, and the dress itself was sold at auction for nearly a million dollars.

 
10 of 25

Worst: Kevin Smith

Worst: Kevin Smith
Photo by GVK/Bauer-Griffin/GC Images

Indie filmmaker Kevin Smith burst onto the scene with "Clerks" in 1994 and then didn't speak to a clerk at a clothing store since. Instead, Smith wore an oversized hockey jersey almost everywhere, along with a pair of the gigantic jean shorts. The jorts were often so big that they almost functioned as extremely loose flood pants. Now that Smith has lost over 60 pounds following a heart attack, he could comfortably wear those shorts with both Jay and Silent Bob in them, too.

 
11 of 25

Best: Elton John

Best: Elton John
Photo by Kevin Winter/Getty Images for NARAS

It's hard to decide what's more impressive: Elton John's extensive collection of designer jackets, or Elton John's extensive collection of designer sunglasses? They both feel like essential complements to Elton, like the piano or Bernie Taupin. But now that Elton is retiring from touring, he'll finally be able to devote his full attention to his jackets and specs.

 
12 of 25

Worst: Kenny G

Worst: Kenny G
Photo by Taylor Hill/Getty Images

America's greatest and only soprano sax superstar, Kenny G, also has the music world's worst hair. He has long locks that are somehow simultaneously curly and stringy at the same time, and looking at them gives you the same feeling as hearing his music, probably while you're in an elevator or waiting on hold. He switched up his leather vests for shiny suits, but the hair stayed. However, the curly look may be in jeopardy, not because Kenny finally came to his senses about it but because they're discontinuing his favorite styling cream.

 
13 of 25

Best: Tom Wolfe

Best: Tom Wolfe
Photo by David Corio/Redferns

The late Tom Wolfe happened upon his signature look by accident. He bought a white suit for summer but found it was too warm, and then when he wore it in December, people got annoyed — which delighted him. He also found it helped with the press. "I’d read the piece and it would say, ‘what an interesting man; he wears white suits.’ And so it was a good 10 years where the suits were a substitute for a personality.”

 
14 of 25

Worst: Pharrell Williams

Worst: Pharrell Williams
THOMAS SAMSON/AFP/Getty Images

Pharrell is good at a lot of things, but finding normal-sized hats is not one of them. What's he hiding under those giant chapeaus? Probably hit records.

 
15 of 25

Best: Karl Lagerfeld

Best: Karl Lagerfeld
Photo by Victor VIRGILE/Gamma-Rapho via Getty Images

The late Karl Lagerfeld saved the Chanel brand and was just as iconic with his personal look: white hair, black sunglasses, fingerless gloves, a detachable, highly starched collar and a tie. Overall he looks like a hit man who went into witness protection at fashion week in Paris.

 
16 of 25

Worst: Mark Zuckerberg

Worst: Mark Zuckerberg
Josh Edelson/AFP/Getty Images

Mark Zuckerberg's signature look was a hooded sweatshirt over a gray T-shirt, and he wore it every single day. Not only did this inspire a whole generation of tech entrepreneurs to dress like slobs, but it also shows that Zuckerberg pays as much attention to his clothes as he does to Facebook's data security.

 
17 of 25

Best: Slash

Best: Slash
Photo by David Wolff - Patrick/Redferns via Getty Images

Slash's iconic top hat has probably seen unspeakable things and been in unspeakable places, but for some reason it works for him. Even if you're not on heroin, it looks great! The look has certainly aged better than bandmate Axl Rose's signature look, which is a bandanna and a kilt.

 
18 of 25

Worst: Bret Michaels

Worst: Bret Michaels
Photo by Donald Kravitz/Getty Images

Speaking of bandannas, Bret Michaels wears one almost constantly, even when he was romancing women on "Rock Of Love." It was a thinly disguised attempt to hide his baldness and elaborate hair weave, and a precarious hair situation like that means once the bandanna goes on, it cannot come off on camera. We also see this when our current president puts on a hat. We're sure Michaels' old bandmates would agree: That look is Poisonous. 

 
19 of 25

Best: Johnny Cash

Best: Johnny Cash
Photo by Beth Gwinn/Redferns

Johnny Cash was "The Man In Black" because he always wore all-black clothing. In the song of that name, he said, "I wear the black for the poor and the beaten down, living in the hopeless, hungry side of town," but is it a coincidence that so many fashion designers also dress in all black? Maybe Cash wore black to be a rebel, or maybe he wore it for good luck after wearing all black in his first show. But maybe he just realized that black is extremely slimming.

 
20 of 25

Worst: Jay Kay of Jamiroquai

Worst: Jay Kay of Jamiroquai
Photo by Brian Rasic/Getty Images

Jamiroquai's biggest hit was "Virtual Insanity," and lead singer Jay Kay's fashion decisions are actual insanity. He's kept up his style of large ridiculous hats and fuzzy outfits, which mostly makes him look like a reggae Teletubby. Somewhat acceptable in your mid-20s; fairly embarrassing in your mid-40s.

 
21 of 25

Best: Amy Winehouse

Best: Amy Winehouse
Photo by JMEnternational/Redferns

Amy Winehouse was a great vocalist in her all-too brief career, and her signature, rockabilly-inspired look was also great. Beehive hairdo, winged eyeliner and tight retro dresses were essentially her uniform, and not just on stage. When she had to go to court in 2009, she didn't ease up on her style one bit.

 
22 of 25

Worst: Jared Leto

Worst: Jared Leto
Photo by Cindy Ord/Getty Images

Academy Award winner Jared Leto is frustrating because of the combination of his insane fashion sense and his apparent inability to age. What's his signature look? Bad decisions. Clashing colors, terrible hats and essentially looking like a homeless drifter who somehow spent $5,000 at a thrift store while on mushrooms; a devastatingly pretty drifter, but a hallucinating drifter nonetheless.

 
23 of 25

Best: Flavor Flav

Best: Flavor Flav
Photo by Catherine McGann/Getty Images

Flavor Flav was the hype man for Public Enemy, but despite wearing a clock as a necklace constantly, Flav was just as political as the rest of the group. The clocks served two purposes: first, it was hilarious, and second, it cast Flav comically, in almost a Shakespearean manner; the fool who speaks the truth. Somehow the clocks are still working for him to this day, even though the fashion police, like the real police, have been gunning for Flav for decades.

 
24 of 25

Worst: Donald Duck

Worst: Donald Duck
Photo by Frazer Harrison/Getty Images

It is wholly inappropriate in the #MeToo era in Hollywood that Donald Duck is still running around not wearing any pants. Maybe when the character first arrived during the Depression, clothes were hard to come by, but now there's no excuse. His uncle is a millionaire! Also, while Donald has always worn a sailor suit and cap, during World War II he served in the Army, not the Navy. Seems like a case of stolen valor to us.

 
25 of 25

Best: Katharine Hepburn

Best: Katharine Hepburn
Photo by ullstein bild/ullstein bild via Getty Images

Katharine Hepburn collected wide-leg trousers like she collected Academy Awards. She shook off the shackles of dresses and skirts and became an iconoclast off screen just as much as she was on screen. Plus she looked great, even though she did say, "dressing up is a bore. At a certain age, you decorate yourself to attract the opposite sex, and at a certain age, I did that. But I'm past that age."

Sean Keane

Sean Keane is a sportswriter and a comedian based in Oakland, California, with experience covering the NBA, MLB, NFL and Ice Cube’s three-on-three basketball league, The Big 3. He’s written for Comedy Central’s “Another Period,” ESPN the Magazine, and Audible. com

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