7 of the Best-Dressed Men in Oscars History
We round up our top picks of all time for the best men at the Academy Awards.
By: Harry Rosen StaffDate: 2026-03-06
When it comes to red carpet fashion, the Academy Awards represent the pinnacle of sartorial excellence. Over the years, Hollywood’s leading men have graced the Oscars with impeccable style — no matter if theirs leans more toward timeless elegance and sophistication or bold, cutting-edge creativity.
Whether classic or contemporary, the most memorable red carpet looks rarely rely on form or flash alone. Instead, they challenge our expectations of traditional black-tie dressing, surprising us with an original twist — exceptional tailoring, refined fabrics, or a thoughtfully considered detail — proving that true style often lies in the nuances.
Brad Pitt, 2020
Brad Pitt, the epitome of effortless cool, has consistently impressed on the red carpet with his understated yet refined style. In 2020, he opted for an elegant Brioni shawl collar tuxedo, which adds a tasteful twist to a classic ensemble — your reminder that you don't always need to opt for peak lapels when wearing black-tie.
Sonny Bono, 1973
Sonny Bono’s 1973 look featured an eye-catching patterned velvet tuxedo jacket, complemented by his iconic statement moustache. Known for his daring fashion choices, Bono embraced boldness with confidence, sporting an outfit worthy of having Cher on his arm and inspiring us to bring a little more flair to formalwear.
Sidney Poitier, 1964
In 1964, Sidney Poitier made history at the Oscars not only with his groundbreaking win as the first African American to receive the Academy Award for Best Actor but also with his impeccable sense of style. Opting for a traditional morning suit, complete with full coat tails and white bow tie, he accepted his award with the utmost style and grace.
Daniel Day-Lewis, 1990
Daniel Day-Lewis, renowned for his transformative performances on screen, also knows how to command attention with his fashion sense. While he often embraces old Hollywood glamour, in 1990, he dared to play with unconventional patterns and colours, opting for a brown polka-dot shirt under a classic black suit — proving brown and black can go together.
Mahershala Ali, 2019
Mahershala Ali's 2019 Oscars look was a masterclass in modern elegance. Wearing a sleek black ZEGNA tuxedo with a subtle paisley pattern, an eggshell mandarin-collar shirt, and a hat that underscored his personal flair, it achieved a near perfect balance of timelessness and modernity. Let this be a lesson to never forget the power of headwear, even on the red carpet.
Jack Nicholson, 1976
With his iconic sunglasses and irreverent charm, Jack Nicholson epitomized the spirit of Hollywood rebellion at a time when films were breaking away tradition. Here, we love Nicholson's larger, more playful bow tie — an old-school look that never truly goes out of style. Try one yourself the next time you want to shake up a standard black tux.
Colman Domingo, 2025
Colman Domingo is consistently one of the best-dressed men in Hollywood, though this is easily our favourite 'fit of his. Somehow through his sartorial prowess, he made a bright red, double-breasted, self-belted cocktail jacket look elegantly sophisticated. If you were afraid to incorporate more colour into your black-tie attire, look no further for inspiration.
Shop EventwearShop All
Win the award for Best-Dressed Lead at your next event — with us today.