Top 20 Oscars Gowns Of All Time

While many Academy Awards moments can go viral – some for the right reasons, and some for the wrong ones – one thing we can always count on is an entertaining red carpet from the biggest actors of the moment.

From Jennifer Lawrence falling in Dior to Michelle Williams in that yellow dress, waiting anxiously for Zendaya to arrive to loudly declaring your own fashion winners from the comfort of your couch, for fashion and movie lovers, the Oscars are akin to our Superbowl or Grand Final.

And so, in a category that may be more contentious than the Oscars themselves, I present – in no particular order – the best ever dresses from the Academy Awards Red Carpet.

A quick note: Here, 'best' means the best looking dresses. Not the most controversial, memorable or award winning –just what looked what I refer to as ''gorj af' (High Fashion term).

Best Oscars dresses on the Red Carpet

1. Michelle Williams in Vera Wang, 2006

Source: Vogue Australia.

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.

2. Mila Kunis in Elie Saab Couture, 2011

Source: Harper's Bazaar.

I remember my jaw literally hitting the floor when I first saw this in motion (well, saw it on the telly). 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, 2008

Source: Marie Claire.

Never really heard much from her after she cruised into the Awards in this amazing gown and won (well, except for her popping up in Morning Wars season 4 where she's so unbelievably hot it's like, I'm not gay but also am I?), 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, 2015

Source: Vanity Fair.

I know many articles praise her 2024 blue Prada as her best, but I much prefer this exquisite creation. 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. Runner up: her gold Prada from 2022. It's giving sexy minx and I'm here for it.

5. Jennifer Lawrence in Dior, 2013

Source: Getty.

She fell. She fell in Dior.

Love her or hate her, this was a most spectacular gown to fall in Dior for en route to accept her Oscar for Silver Linings Playbook. The backwards necklace and dropped waist has a dreamy romantic feel that I appreciate and hasn't really been done since. Beautiful.

6. Sienna Miller in Matthew Williamson, 2004

Source: Marie Claire.

K, hear me out. The bag is obviously awful, 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 (2016, 2014)

Source: Getty.

Both are allowed! Cate loves herself a bit of 3D action on the red carpet, and these are no exception. I love an Oscar holder in the same hue as the award itself (She won in the 2014 gown). She dressed to win, and she looks like a spectacular shiny sparkly statue and I just want to touch everything.

8. Emma Stone in Givenchy Haute Couture, 2017

Source: Getty.

I feel like this dress never really got the full attention it deserved when Emma won in it for the travesty that was La La Land. This could be due to a few things, number one being the absolute catastrophe that was La La Land ACCIDENTALLY being read out as Best Picture. With that extraodinary gaffe making headlines, it made it hard for anything else to take the spotlight. But my hot take for number two? She never twisted in it – come on Emma, we needed a photo of you having fun in the fringe!

That said, it's a stunningly made, timeless and sophisticated gown made for an Oscar winner and she absolutely glowed in it.

9. Halle Berry in Versace, 2002

Source: Vanity Fair.

Holy smokes, this was over 20 years ago and it's still as striking as it was in 2002. While not considering particularly risque now, 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, 2009

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 for The Blind Side, 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.

You can come at me if you want, but I'm in a prayer group with the DA, I'm a member of the NRA, and I'm always packin'!

11. Charlize Theron in Dior, 2004

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. Worn for her Best Actress win for Monster's Ball, she looks absolutely divine.

12. Nicole Kidman in Armani, 2018

Source: Marie Claire.

Yes, THIS is the best Nicky Kidman, not that hideous bird green dress thing everyone yaps on about.

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, with her 2009 L'Wren Scott a fun vintage runner up.

13. Jennifer Lopez in Valentino, 2003

Source: LA Times.

Ah, back in her OG Bennifer days! (Not to be confused with her will-they-won't-they-actually-we-don't-care modern 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, so J.Lo, we forgive you) the elegant detail on the gown made her look less Jenny from the Block and more like royalty.

14. Angelina Jolie in Elie Saab, 2009

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, 2009

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.

This is what she wore when she became the first Spanish actor to win an Oscar for Vicky Cristina Barcelona. 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, 2010

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 on red carpets, 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, 2006

Source: Getty.

Now, this was controversial and made it onto many Best and Worst lists in 2006, but I loved it then and I love it now.

The Brigette 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 Atelier Versace, 2013

Source: Vogue.

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

19. Brie Larson in Celine, 2020

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. Plus, y'all know I'm a sucker for Oscar winners dressing like the statue. it's a shame she didn't wear it when she won in 2016 for Room. (Arguably, this was really Jacob Tremblay's Oscar to win, but I digress).

But hey. Sparkles + shiny + cape = happiness. Brie's come a long way since her handkerchief top over white pants days, and she deserves the credit.

20. Madonna in Bob Mackie, 1991

Source: Getty.

Back before her main thing was using AI filters on Instagram, the legend of Madonna catapulted this glorious Bob Mackie creation into fashion stardom. Channelling her inner Marilyn Monroe, the ensemble went on to be worn by Fran Fine on The Nanny, and most recently, by Sabrina Carpenter at The Grammys. Iconic.

21. Selena Gomez in Ralph Lauren, 2025

Source: Getty.

If ever there was a moment that transformed her from your kid's favourite Disney to starlet to bona fide red carpet glamour, it was this bespoke Ralph Lauren creation featuring over 16,000 drops of glass that made us all take notice of her new style status.

After a string of misfires, Selena's new stylish Erin Walsh decided to put her in old Hollywood glamour looks that made for a stunning red carpet season, cumulating in this custom gown designed as an ode to Italian actress Sophia Loren.

22. Emma Stone in Elie Saab, 2015

Source: Getty.

Worn for her first Oscar nomination for Birdman, this was one of the first films that had audiences consider her a 'serious' actress, with a more adult gown to go with it.

While the chartreuse may not be to everyone's taste, it's a tricky colour to pull off, and I admire that she went for something different (while still sparkly, obv) that was still striking, sophisticated, stylish and sexy.

23. Carey Mulligan in Balenciaga, 2024

Source: Getty.

Oh gosh, get a fan, because this is HOT. Honestly in my personal top five, this Balenciaga dress was like my original wedding dress vision embodying slinky velvet over a tulle mermaid. The flattering shape, the old Hollywood glamour, the classic yet dramatic silhouette, the classic colour combinations – what's not to love?

The Balenciaga design was actually a recreation of the 1951 original, with Mulligan stating that it is the best dress she has ever worn. Agreed!

24. Angela Bassett in Moschino, 2023

Source: Fashionista.

What a saucy broad, amiright? Angela was in her mid 60s in this striking purple ensemble, showing elegance, sexiness and iconic looks can be done at any age and in any colour.

25. Anne Hathaway in Armani Privé, 2009

Source: FashInMosh.

A classically beautiful dress on a classically beautiful actress. I always thought she got an unfair amount of backlash during the 2010s, and I'm loving seeing her in her confident, hot, cool girl era now we're in the 2020s.

Back back to the dress. With both showcasing an ode to old Hollywood, the elegant gown that was covered in silver, pale-lilac Swarovski crystals and sequins was a return to form after the less-than-favourable dress she won the Oscar in for Les Miserables in 2013. Stick to the classics and win.

26. Demi Moore in Armani Prive, 2025

Source: WMag.

Although many thought Demi had the Oscar in the bag for this round, unfortunately she left empty handed when the gong instead went to Mikey Madison for Anora (I have THOUGHTS about all the awards laid on that film, but that's for another time). Even though The Substance literally made me want to throw up in my own mouth by the end, when Demi did win was on the red carpet.

Whether she was in her early 20s or 60s, this was a smashing bejewelled look from head to toe. The custom Armani gown was apparently decorated with 70,000 crystals and 150,000 paillettes (sparkling shiny thingies) allowing Demi her moment to truly shine.

27. Kate Hudson in Atelier Versace, 2003

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.

Anyone that was missed, that you love or hate?

And will anyone join the list for 2026? We'll just have to wait and see...