With the 98th Academy Awards ceremony just around the corner, the question on everyone’s minds, beyond who will take home each award, is who will wear what on one of the world’s most scrutinized carpets. Before the latest wave of sartorial triumphs (and inevitable blunders) hits our screens, CULTURED turned to 14 opinionated authors, actors, and critics to revisit the Oscars ensembles they’d award a golden statue of their own.
Rob Franklin, author
The Look: LaKeith Stanfield’s Saint Laurent jumpsuit
The Year: 2021
Why It Matters: “Scrolling red carpet pics, I often lament the limitations of menswear, until I see a look that revitalizes the whole concept. LaKeith Stanfield’s Saint Laurent jumpsuit was one such look. Sleek and ’70s sexy, it accentuates that snatched little waist of his while still offering a contemporary take on black tie, sufficiently formal for the Oscars. To me, it’s perfection.”
Maya Golyshkina, artist
The Look: Gwyneth Paltrow’s Ralph Lauren dress
The Year: 1999
Why It Matters: “She looked so stunning and ethereal in that soft pink gown, effortlessly glamorous!”
Katey Rich, awards editor at The Ankler
The Look: Michelle Williams’s yellow Vera Wang gown
The Year: 2006
Why It Matters: “It was both wonderfully simple and sneakily daring—that color and fabric can go so wrong on red carpets, but every detail of her gown was perfect, including the red lipstick that went with it. It was her first nomination for what’s turned out to be a stellar career. The fact that it was the only time she ever attended the awards with her then-partner Heath Ledger adds a bittersweet touch of Hollywood myth and tragedy to the whole thing.”
Ivy Wolk, actor
The Look: Liza Minelli in vintage Halston
The Year: 2014
Why It Matters: “She was feeling puss as fuck with a little blue streak in her bangs, flashing a peace sign with one hand and a palm-sized pearl-encrusted clutch in the other. She is wearing non-slip shoes you’d see in a McDonald’s kitchen. Looking a damn mess and so happy to be out of the house!”
Timothy Chernayev, stylist and fashion critic
The Look: Faye Dunaway in Theadora Van Runkle
The Year: 1968
Why It Matters: “I love the shoe, I love the aura, and I love the tension of the hair and makeup against the dress. It was so ahead of its time—a 27-year-old could wear this today exactly as it’s styled and turn heads.”
Biz Sherbert, editor and podcaster of Nymphet Alumni
The Look: Jennifer Connelly in her Balenciaga scarf
The Year: 2002
Why It Matters: “Her flattering ruffles and gauzy neutrals continue to inspire.”
Thor Shannon, art dealer
The Look: Trey Parker and Matthew Stone dressed as Jennifer Lopez and Gwyneth Paltrow
The Year: 2000
Why It Matters: “When they showed up to the Oscars high on acid, it was the most beautiful anyone has ever looked on the red carpet.”
Rian Phin, fashion critic
The Look: Whoopi Goldberg‘s Bob Mackie-designed Queen Elizabeth costume
The Year: 1999
Why It Matters: “It was the same year as Celine Dion’s iconic backwards suit and Gwyneth Paltrow’s pink gown. This costume change was so elaborate, and such a funny contrast against the ’90s red carpet gowns.”
Chris Black, creative director and podcaster of How Long Gone
The Look: Jack Nicholson in a black tuxedo and sunglasses
The Year: 1976
Why It Matters: “Classic in every way, with a slightly floppy bow tie and aviators that fit his face perfectly.”
Aaron Levine, designer
The Look: Robert Redford in a black tuxedo
The Year: 1981
Why It Matters: “Clothing is the canvas, and the individual is the artwork. The coolest in the room is the quietest. Not the loudest clamoring for attention. Quiet, intelligent, confident. That, to me, is individual and special.”
Amy Odell, writer of Back Row
The Look: Björk’s Marjan Pejoski swan dress
The Year: 2001
Why It Matters: “I recall her being pilloried for making that choice because everyone else was basically playing it safe in mermaid gowns, and people weren’t as exposed to fashion as they are today with social media. I think if someone wore that today, it would be much differently received. If you look at it now, it doesn’t even look that crazy.”
Anastasia Vartanian, fashion critic
The Look: Cher’s custom Bob Mackie ensemble
The Year: 1986
Why It Matters: “Bob Mackie and Cher had worked together extensively before this moment, but on this occasion he was initially reluctant. He thought that [the look] wasn’t something you should wear to the Oscars, but Cher didn’t care. She’d been snubbed that year and felt that the Academy didn’t take her seriously because of the way she dressed—so she went all in. I love this look not only because it is fabulous, but the petty and rebellious story behind it makes it even better. The all-black is so perfect because it makes this crazy look work. The headdress looks like it could actually be her hair— it’s just so cool. Today, we’re used to celebrities pulling a look and competing for virality with fashion, but at the time it wasn’t like that. This story is an interesting window into how celebrity culture has evolved.”
Angelica Hicks, fashion tastemaker and performer
The Look: Cher’s custom Bob Mackie ensemble
The Year: 1986
Why It Matters: “Not only because I have recreated it, but has anyone ever looked more fabulous or toned?”
Declan Chan, stylist and creative consultant
The Look: Jennifer Lawrence’s Spring/Summer 2013 Dior Haute Couture gown
The Year: 2013
Why It Matters: “I love the moment that she fell and rose again—it was a fashion moment and so unserious. This Dior Haute Couture gown has the perfect silhouette and fabric. It’s simple yet dramatic, but not screaming for attention. It fits her character perfectly.”
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