All-Time Best Oscar Beauty Moments

Back in 1994, Winona pulled off these ’20s-style waves without looking as if she were off to a costume party. Retro hair is never an easy task to pull off, but we think she was a winner that night.

At the time, Nicole Kidman was the lesser-known half of a Hollywood power couple, but she was always able to stand on her own, especially on the red carpet. Here, her deep-red lips were almost another accessory for her admired chartreuse Christian Dior gown, while her then-strawberry blond hair was pulled into a chic low bun.

We have to say that this look is one of our favorites because it was the year Courtney Love got it right: a sophisticated blond bob, luscious lashes and full red lips. It was a true Hollywood moment for the bad-girl rocker that everyone had been waiting for.

Minnie Driver wowed us in down-to-there tight curls and scarlet lips to match her burgundy dress. It was a matchy-matchy look we were able to get behind.

Drew Barrymore cemented herself into Hollywood hippiedom with her daisies-as-hair accessories and subtle body glitter in 1998. Luckily, she has the lovable personality with which to pull it off!

In our book, sunny Cameron Diaz doesn’t go wrong any year, but in 1998, she turned up in a chic platinum bob and a modern barrette. Her iridescent glow was in tune with her gorgeous white ensemble.

Kim Basinger is the ultimate grown-up Cali girl, and this look is clean, simple and elegant: pin-up girl hair, dewy golden skin, a soft eye and glossy pink lips. It’s a nod to ’50s glamour without looking too retro.

It’s rare to see pin-straight tresses for such a major event on the red carpet, but Helen Hunt looks sleek, modern and glamorous. Glossy lips and soft, smoky eyes take the relaxed look up a notch.

The princess of downtown cool rocked the red carpet in 2000 in a look that was pure Chloe: a short, imperfectly styled bob, bare, bronzed skin and fiery red lips. A plunging neckline and statement necklace completed the look that was, for us, the picture of indie star power.

There is something so cool about Hilary Swank’s overgrown shag at the Oscars in 2000. Her “undone” look looked breezy against her strapless taupe gown. And, of course, her famous pout was super-glossy for the big night.

Brown liquid liner on an otherwise-bare face made the already-perfect Penélope Cruz even more so on the red carpet in 2000. And with her thick mane elegantly pulled back into a bun, her natural beauty really shined.

Sandra Bullock graced the carpet in subtle streaks that were in style way before surfer girl highlights and ombre hair became so popular. We think her soft, tousled look will be in, no matter the year.

In 2002 Nicole stunned us again, but this time with soft, bouncy waves, raspberry lips and subtle eyes. There’s no denying that a simple, effortless look can mean true elegance.

Gwyneth got knocked for this edgy Oscar look, but we know now that she was way ahead of the trend. Try walking down the street without spotting a stylish side-braid!

The super-stylish Julianne Moore turned heads in this forest-green Yves Saint Laurent strapless dress in 2003. Her scarlet hair was swept into a chic side bun, while berry lips and porcelain skin set off the dramatic jewel tone.

We’re not always a fan of throwback waves, but here Charlize hits a home run. Coupled with a soft smoky eye and nude lip…it was a look deserving of a statue.

Though she was merely accompanying Leonardo DiCaprio to the big event in 2005, Gisele’s goddess ensemble dazzled on the red carpet. Her cascading hair and Grecian white dress combo became a look to emulate.

We love Kirsten Dunst for her quirky style choices. Here, her deeply parted platinum bob and charcoal eyes were a youthful way to play up a formal black gown.

Earthy makeup like coffee shadow and taupey gloss added sophistication to Halle Berry’s soft waves in 2005. Though we happen to think that when it comes to this natural beauty, the less makeup the better.

The always-ethereal Natalie Portman will no doubt be glowing on this year’s red carpet, but her 2005 look really wowed us. With hair pulled back into a jeweled headband, soft peach cheeks and honey gloss, she looked like a modern princess.

We’d say Michelle Williams’s show-stopping look, while a bit unexpected, was pretty close to perfection: rosy cheeks, bold red lips and an intentionally messy bun. And her fair skin even looked flawless in a mustard Vera Wang gown.

We loved how Amy Adams accented her gorgeous strawberry hair with bright coral gloss while her green eyes were emphasized with extra-long lashes. Shouldn’t every redhead take a makeup lesson from this starlet?

Voluminous styles can easily go wrong, but Charlize Theron nailed it (again) in 2006. Her teased chignon was offset by pink lips and a bit of liner. Now this is what a movie star should look like.

Cate Blanchett could wear a paper bag to the Oscars and we’d still sing her praises. In 2007 she sported subtle eyes, raspberry lips and soft waves pulled into a low bun. Pure perfection.

A repeat favorite, Cameron Diaz was the epitome of surfer-girl-gone-glam in a sparkly princess gown, side-swept hair, bright red lips and glowy bronze skin in 2010. We can’t wait to see how the blond beauty turns up this year.

Just last year, Zoe Saldana wowed us in this Givenchy couture confection. A subtle plum lip, radiant skin and hair that was effortlessly tossed into a high, loose bun made her an instant style-setter. Who will reign as the red-carpet queen this year?