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7 of the Best-Dressed Men in Oscars History

Here are our picks for the best Academy Award style for men of all time.

By: Harry Rosen StaffDate: 2024-03-08

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 their impeccable style, setting the standard for elegance and sophistication. Among the countless looks, here are a few legendary 'fits we think truly stand out.

Brad Pitt in a tuxedo standing on the 2020 Oscars red carpet

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 impressively elegant Brioni shawl collar tuxedo, which adds just enough of a twist to a classic ensemble.

Sonny Bono and Cher standing next to each other in front of an oscar statue

Sonny Bono, 1973

Sonny Bono's 1973 ensemble boasted an eye-catching patterned velvet tuxedo jacket, complemented by his iconic statement moustache (a moustache that could be ripped from one’s 2024 Instagram explore page). Known for his daring fashion choices, Bono embraced boldness with confidence. However, let's admit it, with Cher by his side, all eyes were inevitably drawn to her.

Sidney Poitier in a tuxedo holding an oscar statue

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 classic black tuxedo tailored to perfection, complete with a white bow tie, he accepted his award with grace and not only redefined Hollywood but also set a timeless example of style and grace on the red carpet.

Daniel Day in a suit and tie holding a folder

Daniel Day-Lewis, 1990

Daniel Day-Lewis, renowned for his transformative performances on screen, also knows how to command attention with his impeccable fashion sense. While he has often embraced old Hollywood glamour in classic ensembles, in 1990, he dared to play with unconventional patterns and colors, opting for a brown polka-dot shirt under a rakish black suit.

Mahershala Ali in a suit holding an oscar award

Mahershala Ali, 2019

Mahershala Ali's 2019 Zegna look at the Oscars was a masterclass in modern elegance and was unanimously declared one of the best outfits of the year. Wearing a sleek black Zegna tuxedo with a refined and subtle paisley pattern, an eggshell mandarin-collar shirt, and a damn cool hat that brought a personal touch to his look, it achieved a near perfect balance of timelessness and modern flair.

Jack Nicolson in a tuxedo holding an oscar statue

Jack Nicholson, 1976

Few can do it like Jack. With his iconic sunglasses and irreverent charm, Nicholson epitomized the spirit of Hollywood rebellion, in a time when films were breaking away from old Hollywood. What we love about his look here is the larger, more playful bow tie that puts an exclamation point on a standard black tuxedo.

Timothée Chalamet in a white suit standing on a blue carpet

Timothée Chalamet, 2018

Timothée Chalamet's 2018 Oscars look was a bold departure from tradition. Sporting a sleek white Berluti tuxedo adorned with a striking black bow tie, Chalamet exuded charm at his first Oscar appearance. He effortlessly captured the attention of fashion enthusiasts worldwide. He’s no stranger to killing it on the red carpet; his 2022 ensemble was a favourite as well.

TAGS:#Fashion,#Events,#Suits,#Tuxedos,#Dress Shoes,#Sport Jackets,