The biggest menswear moments in Oscars history

On paper the Oscars is, to put it simply, the most play it safe of awards ceremonies. The end note of a noisy awards season, it's the most prestigious of all the ceremonies and therefore has historically called for the most elegant of dress, which traditionally means (and as stated by the official dress code) black tie.

And when done right, black tie is always a winner at the Academy Awards. But, among the sea of black tuxedos, there have been some guys who have strayed and come out on top. Look back at the Academy Awards' 95-year history and you'll see a slew of men doing things a little differently. From Prince in bold purple at the 77th Annual Academy Awards in 2005 to the late Chadwick Boseman in glitzy Givenchy in 2019, the Oscars have long been a playground for very subtle menswear moves.

Below are our favourite suited-up men from nearly 100 years of the Oscars...

Sidney Poitier, the Hollywood legend, first African American Best Actor Oscar winner, diplomat and activist, was a master of understated, simply stylish dressing. Case in point: at the 1964 Oscars, where he scooped the award for Best Actor Oscar for his role in director Ralph Nelson's film Lilies of The Field, he wore a subtly cropped tuxedo that's set in motion years of similar tuxedo offsprings on other guys.

Fred Astaire's Oscars dress was consistently classic, and he almost always opted for a one-button black tuxedo, but there was more to it in the finer details His bow tie? Perfectly tied and a little oversized as a marque of the fashion at the time. His trousers featured a silk galon down each side seam and were slightly flared. As much pizzazz as his dancing.

The Chinatown actor wore velvet to the 1971 Oscars in one memorable look, and then a tuxedo, beret and sunglasses to the 1975 ceremony in another. In 1990, pictured here, he took his oversized tuxedo, with which he paird a velvet bow tie, from the Oscars to Swifty Lazar's late night Oscar Party.

In 1981 Robert Redford was named the recipient of the Best Director award for Ordinary People. His golden quaff of hair was brushed back, while his traditional tuxedo was pressed in all the right places.

In 1973 Sonny and Cher, the then-husband-and-wife duo and music partners, matched one another's style power immaculately. With Cher in custom Bob Mackie, Sonny came out with a velvet peak lapel tuxedo, handlebar moustache and that scissor-cut barnet.

Leonardo Dicaprio was nominated for an Academy Award for Best Supporting Actor for his role in What's Eating Gilbert Grape at the 1995 Oscars. He had the guts to rock no bow tie, setting the stage for countless tieless get ups for years after.

Case in point: at the Oscars in 1996 Brad Pitt went tieless in a dagger-point collared shirt, black suit and Neo-esque specs. So very Nineties darling.

In 2005 Prince brought Purple Rain to life as he presented on stage during the 77th Annual Academy Awards. His Seventies-vibing violet jacket was scissor sharp in construction, drawing in his waist and enhancing his shoulders, while his crisp white flares were a nod to his disco era days.

The late Chadwick Boseman came into his own when it came to red carpet dressing. At the 2019 Oscars he wore Givenchy Couture, which consisted of an embroidered jacket that was elongated cape-like at the back and a blouse that featured am elongated chiffon neck tie. In short, the Oscars had never seen anything like it.

A Saint Laurent boy at heart, Lakeith Stanfield rocked up to the 2021 Oscars in a jumpsuit via the Gallic brand that featured an oversized collar in a nod to the French great Serge Gainsbourg.

At his first Oscars in 2023, Paul Mescal, who was nominated for the best actor award for his lead role in Aftersun, wore full Gucci white tie. It had all the movie-star magnetism, bolstered by a custom Cartier diamond floral brooch (and earring).

The slight kick-flare, the lack of tie, the Roystone turquoise buttoned DB. It's the (Louis Vuitton) perfect suit for a guy who has trod many red carpets.

The new star of the red carpet, it was only apt that Colman Domingo shone on the Oscars red carpet in 2024. Custom Louis Vuitton, a smashing bow tie, and lots and lots of jewellery.

Now take a look at the best-dressed men at the SAG Awards 2025

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