Best and Worst Oscars Fashion of the Last Decade

Michelle Williams, Halle Berry and Hilary Swank wowed on the Oscars red carpet. Angelina? Not so much.
Actress Michelle Williams arrives to the 78th Annual Academy Awards. March 5, 2006.
Actress Michelle Williams arrives to the 78th Annual Academy Awards. March 5, 2006. - Getty Images
Stacey Wilson

Watching red-carpet arrivals at the Oscars is the closest thing football-hating ladies like me (and a few select intelligent men) have to a Super Bowl. There are shouts of glee ("She looks amazing!"), groans of pain ("Oh my God, what was she thinking?") and moments of utter disbelief ("Holy sh--. Is she wearing a swan?).

heroes photosSee our Best and Worst Oscars fashion looks

Here is a breakdown of Oscar's most memorable fashion moments. These selections prove you can never spend too much on the perfect dress or, more importantly, a decent stylist.

heroes photosSee the 2009 Oscar nominees

The Best

Halle Berry in Ellie Saab, 2002: The teary Best Actress winner for Monster's Ball stunned us with a rare display of raw emotion in her acceptance speech. But it was her floral-appointed, deep-brown dress -- whose sheer sleeves had been removed just moments before the show -- that blew our minds.

Keira Knightley in Vera Wang, 2006: I'm generally not a huge fan of the droll, wispy Brit's sartorial choices, but this plum-colored, one-sleeved creation was so lush, expertly fitted and flattering, I barely recognized Knightley. Which I'd say is a very good thing.

Hilary Swank in Guy Laroche, 2005: Good Lord, does this two-time Best Actress winner have a body. And what better showcase for it than this second-skin navy dress, whose near-bottom plunging backline turned the long-sleeved gown into the sexiest piece of Oscar fashion I'd ever seen.

Michelle Williams in Vera Wang, 2006: I get a little weepy when I see photos of the Best Supporting Actress nominee and Brokeback Mountain co-star Heath Ledger together on the red carpet, totally in love. Her mustard-yellow dress with the Victorian neckline, accented by red lips, added a sweet dose of romance to the red carpet. If only for a short time, they were the darlings of the ball.

Julia Roberts in Valentino Couture, 2001: This choice surprised me. Roberts has always been a bit erratic and sloppy fashion-wise, so it was fun to see her do old-school glam in a floor-length, only slightly detailed vintage Valentino the night she nabbed a Best Actress Oscar for Erin Brockovich. She'd never looked better, nor has she since.

Penelope Cruz in Chanel Haute Couture, 2008: I couldn't have imagined "navy" and "feather-trimmed" could look so smoldering, but Cruz can turn pretty much any risk into a slam-dunk. The Spanish actress was muy caliente in this full-length couture piece by Chanel, further cementing her place in the annals of the World's Most Ridiculously Beautiful Women.

Charlize Theron in Vera Wang, 2000: No one does 1930s glamour like Theron. Her first major red carpet moment had her slinking into an orange low-back Vera Wang dress, personalized with diamond clips on the straps. Paired with a short auburn 'do, the dress signaled a return to old-school class among Hollywood's hot young things.

Gwyneth Paltrowin Ralph Lauren, 1999: Aw, remember when we used to care about what Paltrow wore? I kid, I kid. Despite being a tad too skinny to make it sexy, the Best Actress winner exuded such a youthful glow in her sweet pink gown, you almost forgot the utter silliness that was Shakespeare in Love.

Rachel Weisz in Vera Wang, 2007: Sometimes, when I pretend I'm a celebrity, I imagine I'm Weisz. (Not in a creepy way, really!) So when I saw her lovely frame draped in this champagne silk gown, appointed by Cartier jewels, I realized ... wow, I'll never be Weisz and then I got sad. But gosh, she looked a might gorgeous that night.

Jennifer Lopezin Valentino, 2003: Oh, J-Lo. If only your aptitude for picking movies in which to star matched your fashion sense. The lovely Latina channeled her inner Jackie O in a 1960s one-shoulder, sea-foam-green gown (it was originally designed for the former First Lady), which was selected by the former Fly Girl just hours before the Oscars.

Worst

Angelina Jolie in Donatella Versace, 2000: The night Jolie won her Best Supporting Actress Oscar for Girl Interrupted is probably most memorable for the, um, special kiss she shared with her brother James. This is probably for the best: her hideous drapey-goth getup was not only a drag, it was downright scary.

Bjork in Marjan Pejoski, 2001: What is there left to say about the most famous fashion misstep in Oscar history? The white tulle swan dress was all Bjork -- silly, impish, slightly insane -- and perfect for a Mother Goose parade float.

Diane Keaton in Ralph Lauren, 2004: Paging Charlie Chaplin! My favorite Hollywood dame of all time, Keaton, has never played it safe. But her multi-layered suit-and-hat ensemble took her 1970s Annie Hall sensibility to an utterly embarrassing level.

Kirsten Dunst in Chanel Couture, 2007: This was a case of a pretty dress -- if a bit busy -- on absolutely the wrong person. The long beaded gown with feather detailing and a sheer collar overpowered Dunst's tiny frame, making her look like a little girl dressing up in a drag queen's cabaret costume.

Celine Dion in John Galliano for Dior, 1999: Ten years later, I'm still recovering from Dion's Kriss-Kross-meets-The Mask getup. The backward white suit jacket paired with an over-sized white fedora proved again there is a fine line between "risk" and "disaster."

Jada Pinkett in Lanvin-Castillo, 2002: The vintage white-and-yellow gown just didn't work on Pinkett. She is too tiny, too chiseled, and overall not girlie enough to pull off such a vintage-princess look. And she scares me a little.

Uma Thurman in Christian Lacroix, 2004: Was it pirate costume? An homage to Heidi of the Alps? Evidence that Thurman had been kidnapped and dressed by folk dancers from the Norweigan consulate? Whatever it was, this layered, gold-accented costume was the usually flawless Thurman's worst red-carpet moment. Ever.

Gwyneth Paltrow in Alexander McQueen, 2002: Oh, how the mighty fell the day Paltrow debuted a most terrible attempt at "edgy." From her bizarre braided 'do, sheer tank (barely containing her small droopy breasts), and thoroughly frumpy black skirt, Paltrow was a hot goth mess.

Faith Hill in Versace, 2002: The rainbow mermaid look is impossible, even on the lovely Hill. This is probably why the singer changed out of her sherbet catastrophe into a simple black dress moments after she left the red carpet.

Tyra Banks in Vera Wang, 2000: Banks' frou-frou lavender puff-dress made quite a statement, which was: "I'm here for the prom, ya'll!" Actually, even by prom standards, this dress was overdoing it, which is something.

Who did we miss? Sound off in the comments!


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