Why *DID* That Look Work?

Academy Museum Gala edition — and just the crème de la crème

On October 18, celebrities reunited for the Academy Museum Gala. To the fashion-savvy people, the event was less about celebration of cinema and the Academy Museum’s exhibitions, and more about our shared passion: fashion.

With many celebrities pulling looks fresh off the runway, others further cementing their deals, and some sporting debut designs, it was hard not to talk about it. And surprisingly, the conversation leaned more love than loathe. So, instead of making a-not-so-big roast of the two or three not-very-pleasant-to-the-eye looks, this week I turned my attention to the brighter side.

I know. The Devil Writes Fashion looking on the bright side? Well, we all have our moments of softness. My moment of weakness involved chatting with some of fashion’s sharpest minds to uncover why their favorite looks truly worked. Don’t worry, you can balance it out by dropping your own roasts in the comments. Or, if you are more into being soft, drop your favorite too.

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ Antonio Padilla AKA @immaculate.style

Chali XCX, Jenna Ortega, and Tom Blyth

“My favorite women’s looks were Charli xcx in Saint aurent and Jenna Ortega in Grace Ling. I love the silhouette of the Saint Laurent gown Charli wore and it looks so elegant in all black. I like how Jenna is taking more risks with her looks this year and it’s paid off. For men since most of them were wearing suits, I really liked Tom Blyth. His Saint Laurent suit looked so clean and the cummerbund around the waist with an unbutton shirt was good styling. A juxtaposition since cummerbunds are meant to be worn with a tux.”

@immaculate.style

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ Molly Elizabeth

Demi Moore, Kaia Gerber, Jenna Ortega

“Ohhh!!!!! I thought the structure on Demi Moore’s gown was one of the finest examples of gown tailoring I’ve seen in a long while. It’s a very simple gown at first glance, but definitely not easy to create. Kaia Gerber in custom Givenchy was a real standout moment for me, and for the trajectory of Sarah Burton’s vision at the house. An all lace gown with integrated lace cape? Sign me up. Finally, Jenna Ortega has been on a complete high fashion roll the past few months, and her Grace Ling ensemble is yet another in her growing repertoire. From hair and makeup to how she poses, she’s a real asset to the red carpet.”

@ladymollyelizabeth

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ Hanan Besovic AKA @ideservecouture

“That stole my heart. I made a video about this dress when it first appeared on the runway. The color, the technique, the flowers, the length… it just works so well and she is wearing it beautifully.”

@ideservecouture

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎@malbwgaf

“Rebecca Hall in Thom Browne Ss26 was definitely one of my favorite looks of the night. The bodysuit immediately caught my eye when it was presented during the last Paris fashion week and I was eager to see it on a red carpet!”

@malbwgaf

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ @jacquemusx

“Crown has to go to Jeff Goldblum. His outfit would have been a hard sell on anyone else but it felt so quintessentially Jeff. Pieces were a crazy combo but it worked surprisingly well. A fresh breeze on the carpet.”

@jacquemusx

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ @italybutoncrack

“Not to be too obvious, but I’d say Kim Kardashian’s look was the most memorable to me. Don’t get me wrong, I loved other looks (like Jenna Ortega, Kaia Gerber looked very classy and so did Chase Infiniti. I also loved Rachel Ziegler’s nod to Marilyn Monroe’s look in Gentlemen Prefer Blondes) but the hint of drama that was delivered through the Maison Margiela look was something I quite liked. I think, when it comes to events and galas that do with museums (yes, even the academy) going a bit out of your comfort zone to match or blend in with what is being exhibited is quite nice. I’m also a sucker for Maison Margiela,so. Oh, also, there was a Thom Browne look that I liked! Forgot who wore it, but the top look like it was a metallic bustier but it was drawn/painted in a way similar to that of Van Gogh’s brush strokes.”

@italybutoncrack

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ Chloe Kennedy

“I loved Jenna Ortega’s Grace Ling ss26 look! I think Enrique Melendez is doing a great job at crafting a style that is unique to her and her body of work that also doesn’t feel like pure costume. my biggest styling critique of the past few years were press tours where celebrities were pigeonholed into these redundant costumes, intended to be referential callbacks (ie. Margot Robbie for Barbie). not only were they lazy, but they stripped the actors of a personal identity outside of the film they were promoting. Jenna, whose catalogue includes several reboots of older films, could’ve easily been the next victim of this, but Melendez styling is guided by semiotics, taking from the themes of her work, which give her these fresh and unique style moments rather than recreations of others’ moments.”

@chloeikennedy

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ @imthespecialk

“I think my favourite one was Brenda Song’s dress! I mean we often think black is a bit traditional but it was just so glamourous and well styled that I was thinking of it hours after the event.”

@imthespecialk

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎@blondiejgp

“Absolutely, Hailey and Kim stole the show! Even though I would have loved to see Hailey with a sleek ponytail or bun because it would’ve really highlighted her features, she’s still one of my top favorites. Plus, her nails perfectly matching the color of her dress was the perfect finishing touch. As for Kim, she completely blew me away! She went all in with a full glam look underneath the veil. There’s something fascinating about one of the most photographed women fully covering herself, yet people can still instantly recognize her just by her silhouette. The corset situation looked kinda uncomfortable, but Kim is not the type to complain because she will always commit!”

@blondiejgp

‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ ‎ Keicia Shanta

Greta Lee, Elle Fanning, and Jenna Ortega

‘‘Greta looked polished, sophisticated and effortlessly chic. Her Dior piece felt like a perfect match for her with sharp tailoring, refined luxe, and just enough edge. Elle gave us something fresh, she stepped into the new era of Balenciaga (under Piccioli) with a playful yet couture-worthy look. The oversized blush top paired with a red feather-skirt from Balenciaga’s Spring/Summer 2026 collection made the moment. I loved the color contrast, the texture mix (feathers + structured top) It was really modern and fresh. Jenna’s appearance felt like a fully formed style moment. The metal breastplate top from Grace Ling paired with a satin skirt turned the traditional gown on its head. It was daring, sculptural and she looked amazing. Jenna has been associated with a more gothic-edged aesthetic, and this felt like a refined version of that world. She leaned into architecture, metallics, and silhouettes in a way that stood out.’’

@keiciashantajenkins