8 Menswear Moments From the 2025 Oscars You Don’t Want To Miss
Build tradition or break a taboo? At the 97th Academy Awards, this was the question of the night.
On one hand, Anora— a genre-bending independent film that stumbles between strip clubs and bounces across Brighton Beach (a Russian enclave in Brooklyn, NY) — took home a staggering five trophies at the 2025 Oscars: Best Actress for Mikey Madison, as well as Best Picture, Best Director, Best Original Screenplay, and Best Editing for director Sean Baker. “Usually subjects like sex work that have a stigma applied to them, and the way it’s been portrayed, hasn’t helped remove that stigma,” Baker told SHARP in November. “I’m looking to make films that help humanize, help bring empathy towards characters that normally don’t have them.” Recognizing Anora, the Academy endorsed original, subversive storytelling from independent filmmakers — a reassuring message, given the onslaught of big-budget remakes and sequels in recent years.
The show itself, however, was curiously tame: boundary-pushing films clashed with a rather strait-laced ceremony. Hosted by Conan O’Brien, the 2025 Oscars took an almost apolitical approach, which drew criticism from outlets like The New York Times and The Guardian, with the latter noting that: “silence can still be pretty deafening.” Others called the Oscars’ fashion evidence of “America’s conservative sweep,” citing an abundance of high collars and lace gloves.
On the menswear side, stars turned up to the red carpet on both sides of the issue. Some embodied tradition — The Brutalist’s Guy Pearce donned a dashing tux — while others broke the dress code with abandon (Adam Sandler’s basketball shorts will surely keep clickbait sites in business). We’ve rounded up a few of our favourite menswear moments at the 97th Academy Awards, from cutting-edge to classic: see the best-dressed men at the Oscars below.
Jeremy Pope
Pose alum Jeremy Pope sported a shimmering ensemble in black satin. Elegant bow button closures and a pair of sparkling rings add intrigue to the understated look. The American singer and actor coupled these chic details with a 40mm IWC Portofino Automatic, complete with a white dial and stainless-steel case.
Andrew Garfield
Andrew Garfield has been at the top of his game this award season, and his look for the 2025 Oscars was no exception. Orange-tinted lenses complement his rich, golden-brown look by Gucci. A silky button-up and sleek shawl collars elevate the edgy colour choice, while a David Yurman necklace and Jaeger-LeCoultre timepiece — the Reverso Tribute Duoface Calendar in pink gold — keep it appropriately elegant.
Matt Bomer
People with blue eyes always know how to accessorize, no? At least, Matt Bomer makes it seem that way. Turning up to the 2025 Vanity Fair Oscar Party, Bomer sported a stunning Reverso Tribute Small Seconds by Jaeger-LeCoultre. He doubled down on the mid-century aesthetic with a dazzling deep blue scarf, high-waisted pants, and a chic brooch pinned to the left peaked lapel.
Jeff Goldblum
Draped in custom Prada, Wicked‘s Jeff Goldblum made us yearn for spring. The SHARP cover alum wore a chic, ivory wool jacket, paired with classic black wool trousers and silky satin bow tie to frame a stunning, polychromatic jacquard shirt. Meanwhile, fresh florals and a lilac crepe de chine scarf recall the botanical accessories of last year’s Met Gala look.
Rege-Jean Page
Arriving to the legendary Vanity Fair Oscar Party, SHARP December cover star Regé-Jean Page stunned in a cotton-silk blend by Brunello Cucinelli. Cast in a captivating brown velvet (did he have a chat with Andrew Garfield?), Page’s tuxedo was a contemporary take on Hollywood glamour, with peak lapels and black wool silk twill trousers to boot.
Sebastian Stan
Though he didn’t manage to snag Best Actor, Sebastian Stan’s pale-yellow silk poplin shirt and custom black wool tuxedo make a compelling case for best-dressed. A gold pin catches the eye, gleaming against the shawl collar, while black patent leather boots and a silk bow tie round out the elegant look.
Colman Domingo
It’s not an awards show roundup without a Colman Domingo mention, and for good reason: the man has been killing it. Nominated for Sing Sing, the Book For Men cover star turned heads with a custom shantung silk jacket by Maison Valentino and an OMEGA Speedmaster Moonwatch in 18K Canopus Gold (with baguette-cut diamonds, no less). The star says his electric red ensemble has a deeper meaning: “I wanted to be the colour of love tonight, so I wore red,” Domingo told ET. “I feel good. I have love around me and I wanted to be love and I feel very blessed and just grounded in what this is. Tonight is just a win already, I’m here.”
Guy Pearce
Earning a Best Supporting Actor nod for his work in The Brutalist, Guy Pearce donned a custom Brunello Cucinelli tuxedo jacket, spun from a velvet cotton silk blend. Striking shawl lapels and understated black trousers create an excellent old-Hollywood look. Accessories are sophisticated and stylish, including an OMEGA De Ville Prestige in stainless steel and a pair of chic glasses with frames in grey mélange.
