Get Oscar Ready: Our 25 Favorite Looks Ever

It’s that time of year again, and the Oscars are fast approaching. Preparations for one of the biggest nights in the film industry have begun, and the world is almost ready for more monumental moments from some of the biggest names in Hollywood.

Stars like Amy Adams, Emma Stone, Lady Gaga, and Rachel Weisz will be gracing the red carpet and taking center stage. The films being celebrated include A Star Is Born, Bohemian Rhapsody, Black Panther, Greenbook and Vice, among other hits that have had the world talking for months.

In 2019, the Oscars are set to take place on February 24 at Hollywood’s iconic Dolby Theatre, where the ceremony has been hosted since 2002. While we can’t wait to see who takes home the big awards, we’re even more excited about the fashion choices that we hope will make history.

Vogue has tapped Versace, Giambattista Valli, Christian Dior, and Chanel to create some of the most captivating looks of this year’s nominees and presenters, so it's bound to be amazing.

Before all is revealed, we thought we'd take a trip down memory lane and remember some of our favorite Oscar looks in history. Do any of these iconic gowns ring a bell?

25 Jennifer Lawrence In Christian Dior


Oh, be still our beating hearts! Jennifer Lawrence in this Dior gown is pure perfection. She wore this look to the Academy Awards in 2013 and we will probably never forget it (and neither will she).

Not only because it’s grand enough to double as a Disney princess ball gown, but also because while she was on her way up to receive her award, she took a stumble on the stairs in front of the whole world. It’s J-Law, though, so she gets away with it.

24 Julia Roberts In Valentino


Julia Roberts was one of the icons of the 1990s, but this vintage Valentino from 2001 shows that she was also winning right through to the new millennium. This piece was originally from 1982, so when Roberts showed up to the Oscars red carpet among custom, totally brand new dresses, she turned some heads.

This move ended up making vintage a more stylish choice, and Valentino later described Roberts in his dress as one of the highlights of his professional life.

23 Keira Knightley In Vera Wang


Keira Knightley in Vera Wang has to be one of the best combinations ever. When the Pirates of the Caribbean actress stepped onto the red carpet in this number in 2006, it was an iconic moment for fashion, and needless to say, waves were made.

And Knightley also proved that she’s as beautiful on the inside as she is on the outside just after the Oscars when she donated this gorgeous dress to Oxfam. The starlet ended up raising £4,301 for charity, which is pretty impressive.

22 Lupita Nyong'o In Versace


On every red carpet, there’s one star who shines a little more brightly than the rest. At the Academy Awards in 2018, that star was Lupita Nyong’o in this Versace gown. We have one word for it: regal.

The fierce gold dress was designed for the Blank Panther actress and featured chain-link details across the bodice and a show-stopping thigh split. Nyong’o completed her look with heels by Alexandre Birman, fine jewelry by Kiwaka, and a Versace clutch fit for a queen.

21 Nicole Kidman In Balenciaga


Brilliant red always impresses audiences, and that’s certainly what happened when Nicole Kidman showed up to the Academy Awards in 2007 in this Balenciaga masterpiece. But it wasn't just the color that was a show-stopper.

The traditional column silhouette suited the actress’s tall, lean figure, but what we really love about this dress is the trailing bow which tied at the back of her neck. This is the perfect example of mixing the modern with the classic, and as always, Kidman pulled it off like a total pro.

20 Anne Hathaway In Marchesa


We’re fans of red… can you tell? At the 2008 Oscars, Anne Hathaway turned up the wow factor by stepping onto the red carpet in this crimson gown by Marchesa. With the asymmetrical neckline and the drape, it had both hints of creativity and elegance, which is probably why we’re still drooling over it more than ten years later!

Marchesa has been one of the most talked about fashion houses in recent years when it comes to dressing A-listers, and we were certainly impressed this time.

19 Emma Stone In Elie Saab


Some would have thought that going for such a pale shade of green when you’ve got porcelain skin would end in disaster, but Emma Stone got this so right. She wore this Elie Saab gown to the Oscars in 2015, and it complemented her porcelain skin like nobody’s business.

This is why we should all take risks more often! Sometimes they turn out splendidly. That said, we can count on one hand the times Stone has gotten it wrong on the red carpet.

18 Penelope Cruz In Versace


More is less on some occasions, but not at the biggest night in Hollywood. If you’re going to go all out with feathers, the Academy Awards is the time to do it.

Penelope Cruz didn’t pick up the Oscar for Best Actress in 2007, but she was all anybody could talk about after strutting down the red carpet in this blush-toned and extravagant Versace gown. Everything is perfect and glam, from the diamonds to the sleek pulled back hair style. We’re still in love!

17 Amy Adams In Versace


Amy Adams likes to rock a princess ball gown from time to time, but at the 2015 Oscar party held by Vanity Fair, she broke tradition and opted for this subtler Atelier Versace piece.

It fits her perfectly and we love the shimmery embroidered detail on the front, but what really draws the eye is the almost cornflower blue. Divine! With the addition of her wavy updo and jewels by Lorraine Schwartz, she was hands-down one of the best looks of the night.

16 Reese Witherspoon In Valentino


Reese Witherspoon has been owning red carpets since her Sweet Home Alabama days. This stunning black Valentino gown had all eyes on the star as she attended the 2002 Oscars to present an award with then-husband Ryan Phillippe.

With the intricate beading work and lace trim, what’s not to love about this dress? Witherspoon didn’t have any wins that night but fast forward to 2007, and she did win an Oscar for the film Walk the Line, in which she portrayed June Carter Cash.

15 Zendaya In Vivienne Westwood


This chic Vivienne Westwood frock marked Zendaya’s debut on the Oscars red carpet in 2015. It’s simple, elegant, and eye-catching, all at the same time, and suits Zendaya to a T. And as glorious as the dress is, Zendaya's hair kind of steals the spotlight.

There wasn’t as much talk about this gown afterward as there should have been because Zendaya’s style was overshadowed by the comments made about her look by a fashion critic. From the experience, however, Zendaya emerged as a strong and confident woman who stands up for herself. You go, girl!

14 Gwyneth Paltrow In Tom Ford


One of the standout looks of the Oscars red carpet in 2012 had to be Gwyneth Paltrow in this high-fashion white Tom Ford gown and matching cape. This was before the minimalist vibe was really in, so it was pretty brave of Paltrow to go down this path, but her daring paid off.

She looked incredible! In the past, the actress has worn a few pieces that have been challenged by critics and fans, but this dress seemed to please just about everybody.

13 Emily Blunt In Prada


Being pregnant is no reason to exclude yourself from the world’s most fabulous fashion. And at the Academy Awards in 2016, Emily Blunt shined in this Prada gown.

With embellishments on the dress itself and on the straps, we thought it was a wise move for the Mary Poppins Returns actress to leave her neck bare. We also loved the chic yet relaxed vibes of her waves and side part. The star never drops the ball when it comes to impressing critics on the red carpet!

12 Amy Adams In Oscar De La Renta


In 2013, Amy Adams went for a subtle style in Versace. But two years earlier in 2013, the American Hustle actress caught eyes and turned heads and she made her entrance in this Oscar De La Renta piece.

The feathered skirt made it seem like Adams was gliding down the red carpet with all the grace of a queen. The Daily Mail reported that Adams worked with the fashion house to get the dress just right, and they were still making changes up until forty-eight hours before show time.

11 Angelina Jolie In Versace


What turned out to be one of the most famous red carpet looks of all time started with Angelina Jolie choosing a Versace gown for the Oscars in 2012. The slit on the right side is what escalated this stunning dress to the next level and paved the way for the term that is now widely in use: the Angie leg.

Jolie popped her leg out through the slit for photos, which is what inspired the concept of posing with the Angie leg.

10 Cate Blanchett In Armani Prive


Not everyone could have pulled off this Armani Prive gown, but we think Cate Blanchett couldn’t have looked more beautiful if she tried. The 3D floral detailing certainly stood out on the Oscars red carpet in 2016, when Blanchett showed up resembling one of the more magical characters from the standard fairy tales.

Not a princess or queen, but a (stunning) fairy perhaps! Fashion commentators noted that this dress was like a tribute to the glamour of old Hollywood, but it also made headlines without looking too dated.

9 Sandra Bullock In Marchesa


Sandra Bullock was the epitome of elegance and style in this Marchesa dress at the Academy Awards in 2010. The metallic gown that skimmed the floor was finished off with glossy locks swept to the side and hot pink lips that added a fun pop of color.

In the end, the actress actually resembled the little gold statue that she won for Best Actress that night for her blockbuster hit The Blind Side. Both Bullock and the dress were winners, but is that really a surprise?

8 Zoe Saldana In Givenchy


Zoe Saldana is another actress who likes to play around on the red carpet, and more often than not, she couldn’t get it more right. 2010 was one such year when she took a fashion risk that totally paid off.

This ruffled gown in shades of purple was by Riccardo Tisci for Givenchy Haute Couture and had people twittering for months afterward. A star with a less bold personality wouldn’t have been able to pull this off, but Saldana looked simply magnificent as she rocked the edgy look with confidence.

7 Grace Kelly In Edith Head


This icy-blue Edith Head gown still gives us all the feels to this day. Grace Kelly wore it to the Academy Awards back in 1955, but before that, she also wore it to the premiere of her film Country Girl in 1954.

When you have a floor-length duchess satin gown like this, though, who wouldn’t outfit-repeat? Kelly paired it with a matching Edith Head shawl, her own jewelry pieces, and white opera gloves, just in case it wasn’t glam enough on its own.

6 Marion Cotillard In Jean Paul Gaultier


This is probably the closest a woman will ever come to transforming into a real mermaid. Marion Cotillard sported this figure-hugging gown by Jean Paul Gaultier at the Oscars in 2008. It may have been because the dress looked like it was made from fish scales, but the actress definitely had people talking.

We think the draping necklaces and side-swept locks were perfect added touches that turned up the magic of the sea vibe. This look is still simply divine, plus it's totally chic in today's times, too.

5 Naomi Watts In Versace


Versace makes miracles happen on the Oscars red carpet, and this Naomi Watts moment is no exception. The actress wore the glitzy dress to the Academy Awards in 2004 and made red carpet history.

The embellishments, column silhouette, and floor-skimming hemline were all traditional touches, but on this gown, at this moment, they looked exquisite. Watts matched the dress with a classic updo and kept it simple with the jewelry, allowing the dress to speak for itself. It worked—we can't stop looking at it!

4 Anna Kendrick In Elie Saab


The blushing pink of this dress seems made for Anna Kendrick’s peaches-and-cream skin tone. This Elie Saab Haute Couture gown, which she wore to the Academy Awards in 2010, made the A Simple Favor actress a winner in fashion, even if she didn’t win any Oscars that night.

She just missed out on Best Supporting Actress, losing to Mo’nique, but we have a feeling the star won’t forget this night anytime soon. How could anyone forget the beauty of a dress like that?

3 Octavia Spencer In Tadashi Shoji


In 2012, Octavia Spencer dazzled at the Oscars and was one of the best-dressed on the red carpet, hands down. This Tadashi Shoji gown fit her like a dream, and is an ode to the true glamour that the Academy Awards are all about!

That night, Spencer was a winner in more ways than one. Not only did she make waves on the red carpet, but she also picked up an Oscar for Best Supporting Actress for her role in The Help.

2 Charlize Theron In Christian Dior


Like we said, there are few places in this world where one can get away with wearing a four-foot train. But the Oscars is definitely the time to be as extra as possible! Charlize Theron stunned in this duck-egg blue Christian Dior Haute Couture gown by John Galliano in 2005.

The actress was there to present the award for Best Actor, but she picked up her own Oscar the year before for her portrayal of Aileen Wuornos in the film Monster.

1 Jennifer Aniston In Valentino


Though she’s one of the most famous and successful actresses of her generation, Jennifer Aniston isn’t one to be dramatic on the red carpet. She tends to go for looks that are simple and elegant.

But in 2013, it seemed that Jen had turned over a new leaf when she swapped her usual safe gowns for this magnificent crimson Valentino Haute Couture number. The Friends star was just there to present an award, but she was the talk of the night.

Sources: Vanity Fair, Marie Claire, Harpers Bazaar, Pop Sugar

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