The Most Stylish Men in Oscar History

On March 10, the Dolby Theatre will once again become the epicentre of the cinematic world, hosting the 96th Oscars. Actors, producers, directors and more will congregate to celebrate the best of film, and better yet, attendees and viewers at home will also get a screening of some incredible red-carpet outfits.

Among the notable nominees are style icons like Bradley Cooper, Colman Domingo, Cillian Murphy, Robert Downey Jr., and Ryan Gosling, each bringing their unique sartorial flair to the red carpet. This occasion offers a prime opportunity for these leading men to solidify their status as fashion trendsetters, following in the footsteps of past menswear icons from the Golden Age of Hollywood to today….

Brando, known for his method acting and intense screen presence, often showcased an unconventional yet captivating style. He won Best Actor Oscars for his powerful performances in On the Waterfront (1954), portraying a troubled ex-boxer, and in The Godfather (1972) as the iconic Vito Corleone. His red-carpet appearances were marked by a unique, sometimes casual approach that set him apart.

Eastwood, a symbol of rugged American cinema, displayed a classic and enduring style. He won Best Director and Best Picture for Unforgiven (1992), a revisionist Western, and Million Dollar Baby (2004), a poignant boxing drama. His red carpet looks often reflected his straightforward, no-nonsense approach to filmmaking and acting.

Renowned for his velvety voice and charm, Sinatra brought an effortless elegance to the Oscars. He won Best Supporting Actor for his role in From Here to Eternity (1953), a film about soldiers in Hawaii leading up to the Pearl Harbor attack. His style was as smooth and charismatic as his performances, often seen in sharp suits that matched his legendary status.

Redford, known for his all-American good looks and serious acting chops, often opted for a blend of traditional elegance and a touch of casual style. He won the Oscar for Best Director with Ordinary People (1980), a family drama exploring the themes of loss and emotional turmoil. His red carpet-fashion often mirrored the grace and depth of his films.

A Hollywood legend, Cary Grant epitomised the epitome of classic style. His tailored suits and debonair demeanor set a standard for red-carpet fashion. Though never winning a competitive Oscar, Grant was awarded an Honorary Oscar in 1970 in recognition of his unmatched persona and body of work that had charmed audiences for decades.

Known for his bold characters and equally striking style, Nicholson’s Oscar wins include Best Actor for the unforgettable One Flew Over the Cuckoo's Nest (1975) and As Good as It Gets (1997), and Best Supporting Actor for Terms of Endearment (1983). His style often included his trademark sunglasses, lending an air of mystery and nonchalance.

Revered for his dancing prowess, Astaire brought the same elegance to his fashion. His Oscars attire was consistently classic, reflecting the grace and precision he exhibited on the dance floor.

Peck's distinguished appearance was a perfect match for his commanding on-screen presence. He won Best Actor for his iconic role in To Kill a Mockingbird (1962), and his style at the Oscars was always the epitome of classic Hollywood elegance.

With a career that spans diverse genres, Jackson's red carpet style is as vibrant and distinctive as his film roles. Though an Oscar win has eluded him, his nominations are testament to his enduring talent.

The quintessential James Bond, Connery's style was effortlessly suave and sophisticated. He won Best Supporting Actor for The Untouchables (1987), and his Oscars appearances were always marked by his debonair charm.

Known for his versatility as an actor, Hoffman's fashion is equally eclectic. He won Best Actor for his roles in Kramer vs. Kramer (1979) and Rain Man (1988), and his Oscars style often reflected his personal quirkiness.

A symbol of British cinema, Caine's elegant style complements his distinguished acting career. He won Best Supporting Actor for Hannah and Her Sisters (1986) and The Cider House Rules (1999), and his appearances at the Oscars were always marked by classic elegance.