The men whose suits, sweaters and small eccentricities still shape menswear.
By Shreya S · Last reviewed 15 November 2026
Who was the first modern menswear icon?
Many would say Edward, Prince of Wales, later the Duke of Windsor. In the 1920s and 1930s he relaxed royal dress with soft-collared shirts, Fair Isle sweaters, suede shoes with suits and bold checks, and the “Prince of Wales” check still carries his family’s name. Fred Astaire, who threaded neckties through his trouser loops as belts, made the same ease look effortless on screen.
Which film stars defined men’s style?
Cary Grant, whose grey suit in North by Northwest (1959) is often called the greatest suit in film. Steve McQueen, with his Harrington jackets, roll-necks, chinos and sunglasses in Bullitt (1968) and The Thomas Crown Affair. Marcello Mastroianni and Alain Delon gave European tailoring its sex appeal.
Why do people talk about Gianni Agnelli?
The head of Fiat was famous for perfect Italian tailoring worn with deliberate imperfections: his watch strapped over his shirt cuff, his tie slightly askew, hiking boots with a suit. The Italians call that studied carelessness sprezzatura. Miles Davis, who moved from sharp Ivy League suits to flamboyant 1970s and 1980s looks, proved that reinvention is a style too.
Who are the menswear icons now?
Musicians and actors who break the old rules: Harry Styles in pearls and gowns, A$AP Rocky and Pharrell Williams, now Louis Vuitton’s men’s creative director, and stars like Timothée Chalamet who treat the red carpet as a playground. In India, Ranveer Singh has done the same. The thread linking old and new icons is confidence. See tailoring explained.
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