Fashion and Style: Hollywood Bad Girls

1
LINDSAY LOHAN
LINDSAY LOHAN
Kate Durbin (Commentary)/ Hollywood.com
Lindsay Lohan has done more drugs and accumulated more clothes than all the other Hollywood bad girls combined. She wins?
2
AMY WINEHOUSE
AMY WINEHOUSE
Kate Durbin (Commentary)/ Hollywood.com
She may wear those dirty ballet slippers all over town, but don’t let their innocence fool you. They tried to make Amy Winehouse go to rehab and every time she said no, no, no!
3
KLOE KARSDASHIAN
KLOE KARSDASHIAN
Kate Durbin (Commentary)/ Hollywood.com
Kloe Kardashian may clean up nice, but that crazy look in her eyes gives away this hard partying reality star as the behind-bars bad-ass she is!
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4
MADONNA
MADONNA
Kate Durbin (Commentary)/ Hollywood.com
Madonna knows that breaking all the rules doesn’t mean you have to look a mess. On the contrary, to be truly rebellious, you must look impeccable at all times.
5
PARIS HILTON
PARIS HILTON
Kate Durbin (Commentary)/ Hollywood.com
Dear Paris, Just because you look like a Barbie girl, it doesn’t mean you live in a Barbie world. Last time we checked, Barbie’s Dreamhouse didn’t come with a little prison in the backyard.
6
SHANNEN DOHERTY
SHANNEN DOHERTY
Kate Durbin (Commentary)/ Hollywood.com
Shannen coined the term “bad girl” with her diva behavior on the set of 90210. She still dresses the part, looking effortlessly tough with her off-shoulder shirt, tousled locks, and aviator sunglasses
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7
TAYLER MOMSEN
TAYLER MOMSEN
Kate Durbin (Commentary)/ Hollywood.com
Tayler Momsen is bad girl to the max with her mermaid locks and lacy panties. She’s even working the pissed-off pout.
8
WINONA RYDER
WINONA RYDER
Kate Durbin (Commentary)/ Hollywood.com
Winona Ryder cemented her bad girl legacy when she played a decrepit version of herself in Black Swan. Here she is trying to look innocent in a white gown—but her facial expression gives it all away!
9
BRITYNEY SPEARS
BRITYNEY SPEARS
Kate Durbin (Commentary)/ Hollywood.com
Oh, Britney. You’re so sweet looking here with your blond locks, lovely smile, and red tube dress. But we all know you’re not that innocent!
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10
CHELSEA HANDLER
CHELSEA HANDLER
Kate Durbin (Commentary)/ Hollywood.com
Chelsea Handler may be dressed like a Beverly Hills housewife, but her caustic, hilarious remarks are just the right dose of naughty to keep all of Hollywood talking!
11
COURTNEY LOVE
COURTNEY LOVE
Kate Durbin (Commentary)/ Hollywood.com
Courtney loved named her band Hole, and, well, just look at her.
12
KELLY OSBOURNE
KELLY OSBOURNE
Kate Durbin (Commentary)/ Hollywood.com
Kelly Osbourne is another star that has cleaned up in the past few years—she looks darling here in her floral mini and denim jacket. But don’t worry—she’s still talking trash when the cameras are off!
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13
KIM KARDASHIAN
KIM KARDASHIAN
Kate Durbin (Commentary)/ Hollywood.com
Kim Kardashian likes to pretend she’s the sweet, serious sister in the Kardashian brood, but we’ve all seen the sex tape. Stop playing, Kim!
14
LEANN RIMES
LEANN RIMES
Kate Durbin (Commentary)/ Hollywood.com
Leann Rimes may look like a perfect country peach, but the drama in her love life is just bad and sad.
15
TILA TEQUILA
TILA TEQUILA
Kate Durbin (Commentary)/ Hollywood.com
Tila Tequila knows that bad girls get badder as their necklines plunge lower!
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16
TARA REID
TARA REID
Kate Durbin (Commentary)/ Hollywood.com
Tara Reid’s been a hot mess since she popped out of the oven with American Pie. Unfortunately her botched surgery, spray tans, and Aeropostale-ish attire are also some kind of pie…dropped on the floor
17
ANGELINA JOLIE
ANGELINA JOLIE
Kate Durbin (Commentary)/ Hollywood.com
Angie’s been Hollywood’s sexiest bad babe ever since she carried a vial of Billy Bob’s blood around her neck. Here she is in a dark gown, about to be crowned Dark Queen. She’s earned it!
18
NAOMI CAMPBELL
NAOMI CAMPBELL
Kate Durbin (Commentary)/ Hollywood.com
Naomi Campbell didn’t get to be a supermodel without a few catfights, as well as a few cell phones thrown at a few assistants. At least she looks lovely in fringe!
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19
NICOLE RICHIE
NICOLE RICHIE
Kate Durbin (Commentary)/ Hollywood.com
Nicole Richie has cleaned up so well since marrying Joel Madden that most of us have forgotten how many dui’s she once had. We’re sure she’s still got some wild child in her, though.
20
LADY GAGA
LADY GAGA
Kate Durbin (Commentary)/ Hollywood.com
Gaga sings a song called “Bad Kids” on her new album, and there’s nothing badder in the best possible way than a woman taking over the world with an unapologetic message and fearless fashions!

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