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The Worst-Dressed Celebrities of All Time

By Edited Aug 3, 2015 1 0

David Arquette(88913)

They’re smart enough to get rich and rich enough to hire stylists, but some celebrities fail when it comes to fashion. While it’s perfectly normal to make mistakes from time to time, a few celebrities are guilty of fashion crimes so heinous that they make Mary-Kate and Ashley Olsen look like Kate and Pippa Middleton.  

Money and fame can’t buy happiness, but it can buy a decent wardrobe. These celebs needs to learn how to say ‘no’ to their fashion stylists and ‘yes’ to things like Goldsign jeans and Joseph dresses.

Richard Simmons

Richard Simmons

Let’s start with the obvious, shall we? Richard Simmons, whose real name is Milton Teagle Simmons, is as famous for his fashion sense as he is for sweating to the oldies. Despite being born with a disfigured upper leg, he rocks obscenely short shorts and the occasional skirt, plus a multitude of low-cut muscle shirts that show off his soft arms. And you gotta love his afro, which is plumped up with hair plugs for an extra lush look. In Richard’s defense, though, he did wear black pants and a suit jacket while visiting Capital Hill. The jacket was purple, but the pants were quite nice.

Bai Ling

Bai Ling

Bai Ling is known for a) wearing as little clothing as possible and b) showing up to every red carpet event possible. Favourite clothing items include fluorescent mesh shirts, thigh-high boots and bras. In case you’re wondering why she’s famous, she’s been in a whole bunch of movies you’ve never heard of. She also played Dr. Valerie Chong in an episode of the Cosby Mysteries.

Helena Bonham Carter

Helena Bonham Carter

Helena Bonham Carter, Tim Burton’s wife and muse, is known for her ‘shabby chic’ fashion sense. Her raggedy style is reminiscent of Vivienne Westwood and Marie Antoinette, but with Elaine Benes’ hair. But at least she knows she looks awful 99.9% of the time: “Sometimes I get it right and I sometimes I get it wrong,” she told People magazine. “For me, fashion is all about fantasy and putting unlikely things together. That’s what I love. I genuinely love dressing up.”

David Arquette

David Arquette

David Arquette is a self-professed lover of clowns, which probably explains his wacky attire. That, or the fact that he grew up on a hippie commune in Virginia. Regardless of his reasons, David Arquette actually has his own clothing line. Named ‘Propr,’ the clothing line is surprisingly cool, with a fun, quirky sixties feel. Go figure.

Jared Leto

jared Leta

Jared Leto’s clothing has its own Tumblr, entitled ‘F*Yeah Jared Leto’s Clothes.’ At first I thought it was a joke, but no, people actually think he’s a swell dresser. They rave about his YSL mesh shirts, his skirts and his mullets and link to knitting directions for his crocheted pink piggy hat. It’s weird, and I don’t like it.

Russel Brand

Russell Brand

Russell Brand, known for his sub-par acting, booky wooks and marriage to Katy Perry, is also famous for his gross fashion style. Tight jeans, deep v-necks, pirate shoes—it’s all wrong. If you don’t agree, consider this fact: Victoria Beckham, Miss Worst Dressed of the Year 2007, is a big fan of his style and lets it influence her fashion designs. But thankfully, for your sake and mine, a Google search for ‘Russell Brand clothing’ brings up a tasteful line of athletic wear, not Russell Brand’s horrific fashion style.

Johnny Depp

Johnny Depp(88910)

I feel bad including Johnny Depp because he’s so pretty, but whatever. Aside from his face, he looks like garbage. There are just too many fedoras, ill-fitting pants and ratty scarves to be attractive.

Pamela Anderson

Pamela Anderson

Silicone-queen Pamela Anderson never gets anything right. One days she’s shows up on the red carpet tangled in a pink satin bed sheet, the next she forgets her pants. Sigh.



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