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The Best Oscar Looks Of All Time

10. Best Color



Nicole Kidman in Balenciaga

Nicole is not the most consistently best dressed actress in the world. But when she steps out for a major red carpet event — no one does it better. When I saw her for the first time in this, I came in my pants and burst into one gargantuan fashion orgasm. With that eye-poppong red, she's saying: "Look at me bitches! See how it's done!" And name any other woman in Hollywood who can pull off that severe bow and cape combo? Charlize tried it once and ended up looking like Quazimodo in drag. Bonus points for not going with an otherwise expected updo. Any neophtye would have with this dress.


9. Most Regal



Jennifer Garner in Valentino

Jennifer Garner is regal? Cute, sweet, and built like a teenage boy — maybe. But regal? That is the genius of this vintage Valentino look that launched stylist Rachel Zoe's career. To say that it was well put together is a grave understatement. This is the best that Jen has ever looked...or ever will for that matter. Marvel at how the exquisite rouching in the bodice hugs her curves and eventually spreads out into a dramatic train. When she walked out on stage, the back skirt flowed so beautifully, like an exotic bird spreading its wings. I nearly crapped my pants. The oversized drop earrings were just the perfect exclamation point to this glorious orange extravaganza.


8. The Sexiest



Charlize Theron in Vera Wang

Speaking of orange — this one takes the cake for the the most jaw-droppingly scintillating orange dress ever hemmed up. As a matter of fact, this girl's career can be summed up in two parts: before and after this dress. This glorious confection, made from layers and layers of paper-thin fabric to achieve its airy feel, literally made Charlize a household name. The styling and silhouette recall Hollywood's Golden Age. When it comes to poise, confidence, and allure, Charlize is truly the gold standard. Bitch.
Kudos to Vera Wang for adding those antique brooches that add character and credibility to the look.


7. Most Chic



Susan Sarandon in Dolce & Gabbana

This bold, fashion-forward, copper number that Susan wore to pick up her Oscar counts as one of the most memorable of all time. From the in-your-face messy do; the naked ears and neck; and the modern ball gown sillhouete — this is self-assured dressing at its best. She outshone every hag half-her age that night. Tres chic!

6. Most Personal


Photo: Evan Agostini, Getty Images

Cate Blanchett in Galliano

If I went to the Oscars for the first time, I think this is exactly what I would want to wear too. Simple, sweet, but with an edge. I love how she downplayed the intricate, whimsical detailing by casually wearing her hair down. It didn't look too "precious" on her. Cate didn't win that night (Gwyneth and her pink, prom vomit of a gown did), but it was her dress was lauded by all the fashion critics the next day. It brought even more glory to the genius that is John Galliano, who reportedly designed the dress with Blanchett over dinner.


5. Most Event-Appropriate



Jessica Alba in Versace

Okay, so "event-appropriate" sounds a little like "Sunday best" or "PTA meeting outfit", but if one were to dress properly for the Oscars, she should look like this. Jessica looked like the Oscar, and that's not a bad thing. The look is glamour personified — perfect hair, perfect bling, perfect dress. Perfect, perfect, perfect. Too perfect, anyone? It looks as if (crazy old) Donatella poured this gold gown directly on to her.


4. Most Ethereal



Charlize Theron in Dior

Nicole Kidman wore a similar dress with the exact same color the year before, right after she had worn another similar dress (in pink) with the same frothy feel for a Chanel No.5 commercial. So you can almost picture Charlize's inner monologue that year: "I'm gonna show that tight-faced hanger who's queen of the red flipping carpet!"
I salivated over this dress for weeks after I saw it. There's only two places you can wear something like this, the Oscars and your wedding. But you'll run the risk of looking like the cake. Cue Enya.

3. Best Winner's Look



Julia Roberts in Valentino

Everybody and their dog's hump buddy knew that Julia Roberts was going to win for Erin Brokovich that night. Julia Roberts knew she was going to win that night — and she made sure she looked every bit the winner. As it turns out, no has ever looked better while picking up an Oscar...ever. As America's biggest movie star, she was very smart to stay away from the princess/debutante route that everyone was going for at that time. Her look was sophisticated, classy — befitting of an accomplished actress whose stardom was on a different plain. But then she came back looking like a poodle the year after to present the Best Actor Award to Denzel. Oh, well.

2. Most Dramatic



Catherine Zeta Jones in Versace

This is the first look that comes to mind when someone mentions "Oscar fashion." For me, it epitomizes how every movie star should look on Hollywood's biggest night. Set against Catherine's raven hair and fair skin, this crimson gown could not have looked better on any actress — living, dead, or thought dead but really living. This is Versace's biggest red carpet home run to date.

1. Most Elegant


Photo: AMPAS

Nicole Kidman in Dior

This dress cemented Kidman's place as the undisputed Oscar red carpet heavy weight champion. It has been for over a decade now and here's why: 1.) It heralded the eventual trend of actresses wearing couture on the carpet. 2. With her tall frame, statuesque figure, and fair complexion, I don't think anyone else could have pulled this dress off the way kidman did. 3.) Does anyone accessorize better? The Indian earrings and East-Asian bracelets? All this without a stylist. Now there's a reason to really hate her!