Jessica Chastain & Billie Eilish: which Oscar winner had the best Gucci look?

Here are some photos of two of the Gucci-clad Oscar winners, Jessica Chastain and Billie Eilish. Jessica won Best Actress for The Eyes of Tammy Faye, and Billie won Best Song for her whisper-singing of a James Bond song. I tend to believe that Jess’s win was much more deserved. I’m tired of Billie winning awards? Especially when her competition was Lin Manuel Miranda AND Beyonce. It definitely felt like the Academy would rather award white mediocrity than Black or Latin excellence.

If this was a clash of who wore the better Gucci, I would be on Billie’s side though. I kind of loved her big, ruffled shower-curtain goth explosion. I like that she put together a real look with hair and makeup and Fred Leighton jewels and it felt authentic to her and she actually looked pretty cool.

As for Jessica… like, girl, can we not? This was so bad! The business at the bottom of the gown was awful. The ombre gold-into-purple was not great. The dress looked incredibly cheap and costume-y to me. It made her look like a worn-out showgirl, and I’ve always thought that Chastain has such a classic, regal kind of beauty. Her husband Gian Luca Passi de Preposulo looked great though!

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Photos courtesy of Avalon Red, Getty and Backgrid.

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49 Responses to “Jessica Chastain & Billie Eilish: which Oscar winner had the best Gucci look?”

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  1. minx says:

    If the top of Jessica’s gown had been continued, into a more form-fitting golden Oscar-y effect, it would have been fine. We’ve seen that look before at awards shows and she’s got the body for it. But looking on down it’s like, whaaa? The bottom is cheesy and doesn’t match at all.

    • Ana170 says:

      The design of the dress doesn’t bother me so much. I think the gold looks bad with her skin tone. It’s worse than the lavender. It should be an entirely different color and made with a much less cheap looking fabric.

      • minx says:

        See, I love the gold tone with her red hair. If I put my hand over the bottom of her dress, the whole look improves imo!

    • The Hench says:

      @Minx – ITA. The ruffle kills it for me and like your idea of more form-fitting gold. I also liked that rose gold colour on her – goes beautifully with her colouring. But, that lilac mess at the bottom – ugh.

    • May Bench says:

      Both gowns were bad, with Billie’s the worst I’ve ever seen. Horrible ugly and funky looking.

    • BudsBunny says:

      I think Jessica had the best look of the night. Hands down.

      Epic dress.

  2. Doublesteff says:

    I don’t know if it’s just the angle or the photos or what but why does Jessica look almost worried when she is smiling? Do I need new glasses? Did the photo agency only upload derpy photos? I’m not sure what I’m seeing but it is definitely not what we usually see with Ms Chastain.

  3. Normades says:

    I love Billie’s dress. It’s different yet on brand for her. Feminine, goth, oversized, fashion forward. A big yes in my book.

    Jessica’s, urgh no. You’re winning an Oscar and this is what you choose? Fugly!

  4. Norman Bates' Mother says:

    I’m very salty about Billie’s win. Dos Orugitas moved me deeply and I can’t believe they snubbed it to give an award to yet another boring Bond theme song. I have nothing against Billy but even in her catalog, there are many better songs than this one.

    • Kate says:

      The academy loves bond movie songs even when they’re not especially good. The last one that won (by Sam Smith), can’t remember the name, also shocked me that it beat out the much better and more moving competition.

    • minx says:

      I’m salty because it prevented Lin Manuel Miranda from an EGOT.

    • Becks1 says:

      I am not a Billie Eilish fan, I feel like she’s someone that the music industry has told us is talented so we are supposed to find her work amazing, but I just don’t like it, not for me. And the Bond song was so meh. SO MEH. Beyonce, Lin Manuel were up in that category, and they gave it to Eilish? Meh. MEH I SAY.

      • Jais says:

        Agree agree agree. To win over Lin and Beyoncé is absurd.

      • Mama says:

        She actually is talented… and it isn’t her fault the Academy picked a Bond song like they do every time a song is nominated from a Bond movie. Just because you don’t like something doesn’t make the person not talented. It doesn’t work that way.

      • TigerMcQueen says:

        This is how I feel. I’ve tried to listen to her work, but the whisper ‘singing’ got old fast. And the win last night once again reminded me why I stopped watching this popularity contest disguised as something special (voted on by lazy people who don’t watch half the movies whose categories they’re voting on).

      • Becks1 says:

        @Mama I didn’t say she wasn’t talented. I said “we are supposed to find her work amazing, but I just don’t like it, not for me.” Others clearly disagree and like her music and that’s fine, but I don’t think think she deserved the win. I understand how things “work.” 🤷‍♀️

      • nutella toast says:

        I have a super broad taste in music (from opera to Patsy Cline to my childhood bossa nova to absolute bliss watching the super bowl halftime this year to pretty much anything on top 40 radio right now) and…I’ve REALLY tried to like B.E. and it’s just not for me. I don’t get it. Not denying she’s talented, but there were much better songs nominated this year.

  5. Pix says:

    I love Jessica and I’m so happy she won. The dress is…fine. She looks amazing and she’s positively glowing. As for Billie, she is mediocre and certainly did not deserve to win. Ugh.

  6. Browniecakes says:

    Jess’ dress had a nightgown bottom ruffle. Maybe if it was more of a column? The top doesn’t look very ‘supportive’ . Can we talk about all the boob baring dresses?

  7. Loco Moco says:

    Both dresses are butt ugly. Not sure what Jessica was thinking. Billie’s fits Billie but still not a fan of it.

  8. Southern Fried says:

    Billie was Billie. Runway look not my favorite but her performance two piece was perfect for her imo. Her hair and makeup is a Yes yes yes! Jessica’s is a nope. Disappointing considering she mostly looks so elegant.

  9. Trina says:

    I thought Jessica had one of the best looks of the night.

  10. MsIam says:

    The skirt of Jessica’s dress kinda ruined it. That ruffle at the bottom did the dress no favors but on film it looked better overall.

  11. Case says:

    Jessica was easily my best dressed of the night. She looked like a winner. Gorgeous dress and loved the styling.

  12. nutella toast says:

    I have a super broad taste in music (from opera to Patsy Cline to my childhood bossa nova to absolute bliss watching the super bowl halftime this year to pretty much anything on top 40 radio right now) and…I’ve REALLY tried to like B.E. and it’s just not for me. I don’t get it. Not denying she’s talented, but there were much better songs nominated this year.

    Also, vaguely remember being forced to watch Jim & Tammy growing up and Jessica NAILED it. Every single bit of it. The only problem is that I now have those songs stuck in my head, and they’re definitely NOT in my internal preferred playlist (“We’re blessed, we’re blessed, we’re blessed….we are bleeeeeeeessssssed”).

  13. lucy2 says:

    I love the top of Jessica’s gown, the copper color on her is great, and it would have been nice if that had been the color the whole way. Blending to that light purple is an odd choice.
    Don’t care for Billie’s look, but it’s hers, for sure.
    I haven’t listened to the nominated songs yet (didn’t watch). I like Billie’s music a lot, but I can’t picture it winning an Oscar.

  14. Cat says:

    Love Jessica’s dress and styling! The bottom of the dress flows nicely imo. Love that shade of purple with her red hair and the shimmering. I dont like Billie’s dress or music, but love her makeup here.

  15. Grant says:

    I kind of liked Jessica’s dress. It looked gorgeous in motion, the fabric had a really lovely sheen.

    I’m over Billie too. The only Bond song that should have won was Skyfall IMO.

  16. Huckle says:

    I think Jessica Chastain looks terrific. Very glamorous and kind of modern retro I think.

  17. Otaku fairy says:

    I love Jessica Chastain’s dress.

  18. L4Frimaire says:

    I prefer Billie Eilish’s gown. She looks like a deadpan crow or that she’s a Christo art installation. It more interesting and very much her. Chastain’s dress is pretty but conventional and that giant ruffle at the hem is swallowing her.

  19. Sara says:

    Jessica’s gown is beautiful but the lights hit the top of it weird almost making it disappear.
    Unpopular opinion: I don’t get the hype over Billie Eilish. She seems cool but the whisper singing isn’t impressive. Maybe I’m just sour that Lin-Manuel didn’t EGOT.

  20. Original penguin. says:

    This is a winner’s dress. She looked the part. You can see the difference when you look at what Nicole and Penelope wore.

    I have to say though I preferred her in green (as always) the colour of the after party dress is gorgeous for her

  21. Twinkle says:

    Jessica’s dress looks like an upcycle from Zsa Zsa Gabor’s costumes from Green Acres. Alessandro Michele should be forbidden to design anything while high.

    Dozens of Hefty bags gave up their life for Billie Eillish.

  22. Janet DR says:

    I think Billie had the best of the dust ruffle looks. Not saying it’s good, but the best 😄

  23. AKA says:

    Wasn’t there a big hoopla about Jessica possibly skipping the red carpet in support of her makeup team who wouldn’t be a part of the televised nominees? Yeah, actors be actors and not miss a chance for attention.
    This is a good dress on her but still have seen her do better. Jewel tones look absolutely stunning on her so wish that’s what she wore for her winning moment. I wish this wasn’t the movie she won for, but the Academy sure loves their prosthetics. She is deserving of an Oscar for her myriad other roles so I’ll consider this as a win for her career.

  24. KG says:

    Jessica’s gown looked really pretty in motion. It doesn’t translate in a photograph quite as well as it did seeing her move in it.

  25. Courtney says:

    I think Chastain’s dress was meant to be a nod to Tammy Faye. The pastels, the ruffles, the sparkle.

  26. Misha Nova says:

    I think I would have liked Jessica’s dress a little more if it was all lavender. The bronze to lavender ombre is a little strange. It has a 60s nightgown vibe that I like, though. At least, it wasn’t another boring Oscar winner dress. She took a risk and I like that.

    I hate Eilish’s EMO outfit and dour face. SO ART-IS-TIC! SO Edgy! Maybe, I’m mad because I don’t think she deserved an Oscar for that awful song. Certainly not over Lin Manuel Miranda. The entire Academy should do a walk of shame for that terrible choice.

  27. Matilda says:

    I hate Jessica’s dress, it looks like a costume from the Love Boat and there are the skins of dead muppets at the hem. Her after party dress, look and makeup was KILLER!!!! I don’t know why she didn’t go with that dress. This girl has it all, handsome aristocratic husband, two kids, beauty, talent, riches and now an Oscar. She has a charmed life for sure.

  28. Colleen says:

    Gold and purple are my favorite colors so honestly, I loved Jessica’s dress.

    Count me among the list of Millennials who don’t get Billie Elish. And honestly, I get generational gaps but the dress was ugly.

  29. Maryscott OConnor says:

    Uh… Chastain’s win was marred SOLELY by the fact her dress looked like a mermaid met a drag queen and they collaborated on the thing Jessica Chastain will now FOREVER be wearing in picture of her Oscar win.

    Her speech was equally as touching and articulate and meaningful as those of DeBose and Kotsur; what a night for great, non-laundry list speeches from the acting winners! I wish we could include Smith in that list, and that’s yet another disappointment about his heinous act: he probably had a terrific (albeit equally disingenunous) speech planned, and instead he had to use that historic moment to do a desperate, massive piece of damage control.

    (If Will Smith didn’t deserve the Best Actor Oscar for playing Richard Williams, he sure as HELL earned it with that buIIshit speech.

    I didn’t buy a second of it, but MAN, now THAT was some stellar acting. Dude worked his ASS off doing some desperate damage control.

    Please note, however, the blatant refusal to apologise to the one person who was OWED an apology.

    Fukc this guy. He’s always been an asshoIe; he’s just been REALLY vigilant about maintaining his jovial, hail fellow well met image. Sure blasted all that PR straight to hell in 45 seconds flat, eh?

    So, yeah. A lot to unpack, but I’m so exhausted by the baffling discussions and arguments I’ve had about te assault that I’ve simply no ENERGY left to give a proper reaction to the Oscars, which I felt was one of the better broadcast in years – until Smith ruined it. Even Amy Schumer killed it (aside from the seat-filler/disrespecting Kirsten Dunst clunker).