The 15 Most Iconic Oscars Red Carpet Looks

by Kali Borovic

The Academy Awards is the biggest awards show of the year, which means it brings out some of the fabulous outfits. From big ball gowns to tight-fitting dresses, this red capet has it all. The most iconic Oscar dresses of all time all have one thing in common — they're major stand-outs. Whether they're on the best or worst-dressed list doesn't matter, because these dresses deserve a category all of their own.

In the past 88 years of Oscars history, some seriously stunning looks have graced the red carpet. Short, long, colorful, muted — nothing is off limits at the Oscars. Each actor embraces their own personality with their style, making for an always entertaining show. Sure, the night might be all about the awards, but the style is always a really fun bonus — and just as important as who takes home a golden statue, in my opinion.

From Angelina Jolie's silk slip dress to Lupita Nyong'o's pale blue twirls, the most iconic moments are the ones you never expect, but can't seem to get them out of your head once your see them. I can't wait to see which outfits from this year's ceremony earn a place on this list, but for now, here are the 15 most memorable fashion moments in Oscars history.

1. Kate Hudson In 2014

Jason Merritt/Getty Images Entertainment/Getty Images

Does it get any more stunning than this? Hudson came out of nowhere in this caped Atelier Versace gown that completely stole the show.

2. Sandra Bullock In 2010

Alberto E. Rodriguez/Getty Images Entertainment/Getty Images

Bullock wowed and won Best Actress for The Blind Side in this golden-hued gown.

3. Lupita Nyong'o In 2014

Christopher Polk/Getty Images Entertainment/Getty Images

Not only is this dress iconic for the way it twirled down the carpet, but it was the first look Nyong'o wore to the Oscars.


Her pearl Calvin Klein gown, which was apparently stolen from her dressing room, also deserves an honorable mention for most iconic of all time.

4. Sarah Jessica Parker In 2010

Frazer Harrison/Getty Images Entertainment/Getty Images

The Sex and the City star looked fabulous in the Chanel pale yellow gown. This wasn't your typical strapless gown and the choker-styled scarf definitely gave it a timeless feel.

5. Jennifer Aniston In 2015

Jason Merritt/Getty Images Entertainment/Getty Images

Even though this dress was nude, it was definitely a stand-out.


Aniston's Atelier Versace gown got more beautiful with every close-up shot.

6. Björk In 2001


Björk's swan dress didn't exactly get her on the best dressed list in 2001 — or ever, for that matter — but it's iconic for sure.

7. Gwyneth Paltrow In 1999

Vince Bucci/AFP/Getty Images

This puffy pink princess dress was the star of the late '90s Oscars.

8. Emma Stone In 2015

Jason Merritt/Getty Images Entertainment/Getty Images

Stone's high-slitted Elie Saab dress was such a different pattern and color than anything she'd worn before.

Kevork Djansezian/Getty Images Entertainment/Getty Images

What was really incredibly about this look was how great it was from every angle.

9. Angelina Jolie In 2004

Vince Bucci/Getty Images Entertainment/Getty Images

Channeling her inner Marilyn Monroe, Jolie's simple silk dress was timeless and elegant.

10. Halle Berry In 2002


Berry brought a start to the barely-there dress trend with her Elie Saab half mesh gown.

11. Cate Blanchett In 2011

John Shearer/Getty Images Entertainment/Getty Images

This Givenchy Couture gown combined beading and soft, flowing fabric for one of the most stunning looks of all time.

Frazer Harrison/Getty Images Entertainment/Getty Images

Just look at the back!

12. Sharon Stone In 1998

Evan Agostini/Hulton Archive/Getty Images

This menswear meets feminine look is so memorable.

13. Michelle Williams In 2006

L. Cohen/WireImage/Getty Images

Williams brightened up the entire red carpet with her mustard yellow Vera Wang dress. Who says the early 2000s weren't stylish?!

14. Reese Witherspoon In 2015

Jason Merritt/Getty Images Entertainment/Getty Images

Witherspoon has had a lot of fabulous looks at the Oscars, but this was by far her most timeless.

15. Barbara Streisand In 1969

ABC Photo Archives/Disney ABC Television Group/Getty Images

Streisand rocked the heck out of this mesh pantsuit, making it one for the books.

I can't wait to see how this year's fashions will compare!