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The Best and Worst Fashion of All Time

The 25 all-time best looks — and the looks best forgotten — in movies and TV …

Best Dressed!
Bram Stoker’s Dracula

Gary Oldman

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It’s the original sexy vampire. Oldman’s dapper Dracula makes Twilight‘s Edward Cullen look like a J.Crew pansy.

KEEP READING: Honey, nuh-uh, girl! [PAGEBREAK]

Worst Dressed!
Honey

Jessica Alba

Alba takes Britney‘s ‘Baby One More Time” look to a superghetto wet-look hair level.

KEEP READING: Oh, yes, the force is strong! [PAGEBREAK]

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Best Dressed!
Star Wars

Carrie Fisher

Princess Leia is confidently badass in both her gold concubine bikini and clingy sheet dress.

KEEP READING: Why would even a bloodsucker dig this?! [PAGEBREAK]

Worst Dressed!
Twilight

Kristen Stewart

With this ad-hoc prom ensemble, Bella is trying way too hard to look like she’s not trying at all. Nice Golden Girls cardigan (scoff).

KEEP READING: Almost Famous, definitely chic! [PAGEBREAK]

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Best Dressed!
Almost Famous

Kate Hudson

Penny Lane’s crocheted dresses, lacy tops and high-waisted jeans (all paired with her eternally present fur-trimmed mountain-man jacket), make it nearly impossible to watch Almost Famous and not want to be a 1970s-era groupie, ahem, band-aid.

KEEP READING: So You Think You Can … dress? Ha! [PAGEBREAK]


Worst Dressed!
So You Think You Can Dance
The contestants (all of ’em)

Why do these poor dancers look so ridiculous — always?! The contestants are clearly talented, but it’s hard to concentrate on technique when way wrong outfits like what’s pictured above (Aladdin 1, Aladdin 2!) are sported onstage.

KEEP READING: Franco is Milk‘s adorable boy-toy! [PAGEBREAK]

Best Dressed!
Milk

James Franco

Track jackets, skin-tight jeans and porno ‘staches are arguably not the most flattering accoutrements for a man. However, Franco rocks all of the above and is a symbol of romantic fantasy. Do show us how you zip those jeans up, Mister …

KEEP READING: Bustin’ out! [PAGEBREAK]

Worst Dressed!
Baywatch

The lady ‘lifeguards”

These wedgerific, cleavage-smashing red one-pieces (oh those shameful tan lines) were the cause of drowning accidents.

KEEP READING: Screw Atonement! [PAGEBREAK]

Best Dressed!
Atonement

Keira Knightley

Ohhh, that green dress. James McAvoy had Knightley up against a wall of books, and the delicate spaghetti straps of this emerald gown slipped off of her shoulders in one of the most passionate lovemaking scenes in history. Sigh.

KEEP READING: Chuck Bass, so matchy-matchy! [PAGEBREAK]

Worst Dressed!
Gossip Girl

Ed Westwick

We get it, Chuck. You’re rich. You’re misunderstood. But you’re not Jay Gatsby, and you look ridiculous in all of your Skittle-colored boy suits.

KEEP READING: You’ll wanna dance, trust!  [PAGEBREAK]

Best Dressed!
The Ellen DeGeneres Show
Ellen DeGeneres

Ellen’s tailored pants, hip kicks, cute vests and skinny ties epitomize laid-back cool couture. Justin Timberlake, you must agree … because you’ve completely lifted Ellen’s look. 

KEEP READING: Hugh’s bunnies are better off naked! [PAGEBREAK]

Worst Dressed!
The Girls Next Door
Holly Madison

So much velour. So many kneesocks. Nudity, please, we beg of you.

KEEP READING: One, two, Freddy’s coming for you! [PAGEBREAK]

Best Dressed!
A Nightmare on Elm Street
Robert Englund, aka Freddy Krueger

The iconic striped sweater, the jaunty hat and, yep, the gloves make Freddy the most debonair of horror-movie killers.

KEEP READING: This look is the Pitts! [PAGEBREAK]

Worst Dressed!
Burn After Reading

Brad Pitt

Tool level: high. Note the frosted tips. And he’s serious about that shirt.

KEEP READING: Alabama slamma! [PAGEBREAK]

Best Dressed!
True Romance

Patricia Arquette

Arquette’s Alabama is a hooker, sure, but she gets major cute-as-a-button points for rocking cowhide miniskirts, gauzy tops and candy-colored underthings. ‘Bama’s definitely the most stylish heroine to strut from the confines of Quentin Tarantino’s bordello of a mind.

KEEP READING: A little Rocky! [PAGEBREAK]

Worst Dressed!
30 Rock

Tina Fey

Liz Lemon’s bedraggled, workaday look is dumb. And it’s because we know how smokin’ she looks for the occasional date — note “occasional.” She can blame her schlumpy-chump outfits for that.

KEEP READING: Law lays down the sartorial law! [PAGEBREAK]

Best Dressed!
The Talented Mr. Ripley

Jude Law

As Ripley‘s Dickie Greenleaf, Law displays immaculately tailored Italian style and the confident swagger of a man who doesn’t want for money or women. Has anyone ever been sexier than Jude in this movie?

KEEP READING: Walk the plank, argh! [PAGEBREAK]

Worst Dressed!
Pirates of the Caribbean

Johnny Depp

Yeah, we know, Depp crafted the look after Keith Richards, it’s a brilliant performance, he’s Johnny-freakin’-Depp … blah, blah, blah. But just imagine what’s under that bandana … and how it might smell.

KEEP READING: Belle of the ball! [PAGEBREAK]

Best Dressed!
Beauty and the Beast
Belle

The gold dress that launched a million beautiful Halloween costumes.

KEEP READING: Diane Court, you blind! [PAGEBREAK]

Worst Dressed!
Say Anything

John Cusack

Yeah, we’re still filled with Lloyd-Dobler-longing whenever we hear “In Your Eyes,” but Cusack’s trench coat, tucked-in tee and Hammer pants are positively unlovable.

KEEP READING: Bangin’ bitch! [PAGEBREAK]

Best Dressed!
The Brothers Bloom

Rinko Kikuchi

Scarlet-lipped sidekick Bang Bang shoots away at her victim. Who’s her victim? Barbie, that’s who. Because she’s an unfashionable bitch.

KEEP READING: Ain’t no Joy to look at! [PAGEBREAK]

Worst Dressed!
My Name Is Earl
Jaime Pressly

Pressly’s jorts-sporting, tubetop-tugging, obscenity-spewing Joy Darville is a vision of WT trash. Best Supporting Actor? Endless can of a hairspray.

KEEP READING: Butcher in a top hat! [PAGEBREAK]

Best Dressed!
Gangs of New York

Daniel Day-Lewis

Bill “The Butcher” Cutting’s style is two parts Victorian gent and one part Willy Wonka. Lewis’ kaleidoscopic look makes his crazy-like-a-fox psychopath even scarier and, well, hot.

KEEP READING: Miss J-anky? [PAGEBREAK]

Worst Dressed!
America’s Next Top Model
Miss J Alexander

The expanding bow ties, the horrid bowl cut — Miss J’s outfits get more clownish with each new cycle. Sure, he (er, she?) has to do something to compete with Tyra’s self-obsessed yakking, but ugly ain’t pretty — like Tyra wants us to believe.
 

KEEP READING:We’re Mad about it! [PAGEBREAK]

Best Dressed!
Mad Men

The entire cast

Mad Men’s impeccable style makes us yearn for the old-school propriety of the ’50s-era elite. From cardigans to cuff links, every single perfectly coiffed secretary nails the boardroom-to-bedroom look. Don Draper makes us swoon, and Betty Draper has us wishing that laundry-doing — while clad in a big-skirted frock — was our career, too.

MORE: Wait, What’s the Age Diff?

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