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Top 20 Oscars Gowns Of All Time

Updated: May 1, 2020

Look guys, Ima let you finish...but Michelle Williams had the greatest Oscars gown of ALL. TIME!

We were lucky to get the Oscars this year and critique fashions from the comfort of our couches with popcorn and sweat pants a plenty. However, since Cannes and the MET are postponed, let's get our fashion fix with a gaze at, in no particular order, the Top 20 Oscars Gowns of All Time.

Note: Top 20 means the best looking dresses. Not the most controversial, memorable or award winning - just what looked 'bloody great'! (fashion term).

1. Michelle Williams in Vera Wang

Source: Vogue Australia

And in THIS picture in particularly, we easily know our #1, even though I just said there's no order. Whatever. That yellow Vera Wang, the dreamy look in her eye at Heath Ledger looked on adoringly. The dress, the lips, the jewellery that shouldn't work but does, and of course, the arm candy...ICONIC. I miss their love!

2. Mila Kunis in Elie Saab Couture

Source: Harper's Bazaar

I remember my jaw literally hitting the floor when I first saw this in 2011. She'd just done Black Swan, she came to win, and left giving us The Spy Who Dumped Me. I'm fine with it.

3. Marion Cottilard in Jean Paul Gautier

Source: Marie Claire

Never really heard much from her after she cruised into the Awards in this amazing gown and won, but that's cool. You just want to reach out and flip the scales up and down like the sequin tops all the youths are wearing these days. A fishy, fishy, fishy...

4. Lupita N'yongo in Calvin Klein

Source: Vanity Fair

Now, I've included this grid so you can see the workmanship on this amazing gown. Gosh I'd feel expensive in this. I wouldn't let anyone touch me. I'd never be allowed to wear it though, I'd mistakenly unravel the whole thing because I just had to touch every single pearl in the car on the way over.

5. Jennifer Lawrence in Dior

Source: Harper's Bazaar

Love her or hate her, this was the dress where she had The Dramatic Fall. A most spectacular gown to fall in Dior for, and the backwards necklace and dropped waist has a dreamy romantic feel that I appreciate and hasn't really been done since.

6. Sienna Miller in Matthew Williamson

Source: Marie Claire

K, hear me out. The bag is obviously hid, and the cheating partner has less to be desired. But this was Sienna's launch, and I like how she kept her gypsy-boho-2004 vibe thing going on the red carpet. Also, I remember seeing it in NW magazine when I was like 15 and declaring her beautiful, so basically deciding I had 'discovered' her before everyone else. It's like sexy red carpet wench, and I'm here for it.

7. Cate Blanchett in Armani

Source: Marie Claire

Cate loves herself a bit of 3D action on the red carpet, and this is no exception. I love an Oscar holder in the same hue. She dressed to win, and she looks like a spectacular shiny sparkly statue and I just want to touch everything.

8. Kate Hudson, designer unknown

Source: Glamour

If anyone knows the designer, let me know! This was early days Kate when she was being Penny Lane IRL, like SJP continues to do a la Carrie Bradshaw. I dug it, the whole thing felt different and cool and chic on Kate, and I wished she leaned into this hippie vibe more on the red carpet and in her movie roles. Don't get me wrong - Bride Wars is amaze. But more Almost Famous so we get dresses like this pls.

9. Halle Berry in Versace

Source: Vanity Fair

This was pretty OUT THERE in its heyday. Worn when she was the first African American to win, she also got #1 on the red carpet the world over for this intricate gown designed to perfectly fit that bod that DOES NOT BLOODY AGE. The bodice may fit my arm?

10. Sandra Bullock in Marchesa

Source: The Daily Mail

Who doesn't love themselves a bit of Sandy B? As I said, can't resist a winner in gold, and S.B is no exception. Even though that piece of sh*t she was married to got a free ride to the Oscars that night (Hi Sandy, I am available next time) she looked amazing, she won, and has continued to deliver her signature gold characteristics in classics like The Heat (solid) and (controversial opinion) - the best space film, Gravity. Piss off, Interstellar you LITERALLY DON'T MAKE SENSE.

11. Charlize Theron in Dior

Source: Marie Claire

I would give my right arm to look this hot in this dress. On most, it would look like a nude body stocking, but on Charlize, simple, elegant and sparkly. She looks divine.

12. Nicole Kidman in Armani

Source: Marie Claire

Yes, THIS is the best Nicky Kidman, not that hideous bird green dress thing everyone yaps on about. Yuck, so 90's. Go get a choker and listen to some Teen Spirit while you're at it. I'm a sucker for kitsch, so the slinky royal hue with a fun bow in the middle took this from boring to cutesy, while the jewels keep it elegant and on brand. I dig it.

13. Jennifer Lopez in Valentino

Source: LA Times

Back in her Bennifer days, this was a more demure look for the usual slender sparkly LOOK AT MY INSANELY HOT GLITTERING BOD J.Lo, inspired by a sari once worn by Ms. Jackie O. Whilst the tiger hair streaks have something to be desired (we all did it, we forgive you) the elegant detail on the gown made her look like royalty.

14. Angelina Jolie in Elie Saab

Source: Just Jared

Okay, let's call a spade a spade. Is the dress that great? No. Is it memorable, or even nice? Who knows! I've forgotten it already. All I can say is, with that face, and those earrings, this look became iconic (in the right way, and not the wrong way like she did with the leg fiasco...we won't be including that).

15. Penelope Cruz in Pierre Balmain

Source: Harper's Bazaar

I've always appreciated Pene on the red carpet, cos she brings it 110%. Hair, jewels, make-up, dress, none of this scaled back, naturale garbage. I look at this and think, 'Yes. THAT is what you wear to the Oscars' while I shove another Tim-Tam into my mouth. Or it could be worn to your own royal wedding, covering those provocative shoulders. It's timeless, and elegant, and basically, I'm fomo it's not me wearing the whole thing. Can someone invite me to an Awards show ASAP? I'll bring the snacks!

16. Cameron Diaz in Oscar de la Renta

Source: Red Carpet Fashion Awards

Cammy!! Gosh I loved her on the big screen. COME BACK!! You can't watch The Mask or The Holiday with me, I spend the whole time saying, 'Gosh she's so pretty...gee she's pretty...she's just so pretty!' and in this, you get it. She's normally pretty laid back, but it was great to see her truly bring it in this beautiful creation from ODR. We miss you Cam!

17. Charlize Theron in Dior Haute Couture by John Galliano

Source: The Daily Mail

Now, this was controversial and made it onto many Best and Worst lists in 2006, but I loved it then and I loved it now. The Bridgette Bardot sexy hair, the slink of the waist, the bow for LOOK AT MOI WOW FACTOR, all over it. The best part was her losing it when Crash beat Brokeback Mountain to Best Picture, she couldn't help it and starting pissing herself laughing. Loved it.

18. Halle Berry in Versace

Source: Vogue

I don't feel I need to write anything. Lady is over 50. Just...LOOK at her.

19. Brie Larson in Celine

Source: Popsugar

While the shoes aren't to my personal taste (bit of Bat Mitzvah vibe) and I don't dig shower hair on the red carpet (slicked back bun is what we do in iso hun, not outside) I'd encourage you to look at this dress in movement. Sparkles + shiny + cape = happiness. Brie's come a long way since her handkerchief top over white pants days, and she deserves the credit.

20. Kate Hudson in Atelier Versace

Source: Harper's Bazaar

We end with Kate hitting double points, in what I always deem a winner: gold, sparkly, well-fitted, and well styled. 10/10, Golden Girl. Now, do a movie with your mum about First Wives Loosing a Guy in Ten Days Before Their Bride Wars. We're all counting on you.


Disagree? Let me know your (incorrect) opinions below!

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