The 20 greatest style icons of the 20th Century

From world leaders to movie stars, meet the men whose inimitable style lives on today

Throughout the generations there have been who have perfected timeless style like no others. Whether it be their impeccable tailoring, their choice of separates or the attitude with which they wore them, some men just had it. If you’re looking for some inspiration for your new season style, you could do far worse than take a lead from our pick of the 20th Century’s most stylish men…

Gianni Agnelli

Businessman and Fiat boss Gianni Agnelli perfected the art of imperfections, bringing his Italian effortlessness to the rest of the world. Famed for his eccentric look, he created his own style by slowly and meticulously breaking the rules until he found what worked best for him. A true original.

Gregory Peck

Not only was he enviably good looking, but Peck also showed the world how to wear off-white three-piece suits, which is no mean feat. A firm believer in a good tailor, Peck defines the 50s style of the silver screen like no other.

Sean Connery

Everything about Sean Connery is iconic – from his famed film roles to that incredibly mimicable voice. But it wasn’t just what he wore that makes Connery one of the greatest style icons in history, it’s also the way he wore it – with grace and that panther-like walk.

Cary Grant

Throughout his life Anglo-American actor Cary Grant stayed true to his British roots, seemingly determined to prove that there was no better tailoring than that on Savile Row. His dedication to the world of tailoring – plus his penchant for sporting covetable off-duty separates – only enhanced his style icon status.

Steve McQueen

The 20 greatest style icons of the 20th Century

We can think of few men throughout history who have done more in the promotion of jeans, cable-knit sweaters and leather jackets than this man, the King of Cool. In fact, so great is his style status, that we’re still keen to dress like Steve McQueen now.

Paul Newman

Having said that… maybe Newman could give McQueen a run for his money. While McQueen found his niche in hard-edged casualwear, Newman’s style covered the whole spectrum. From classic black tie to versatile weekend looks, there are few Newman outfits we’re not still coveting decades on.

Aristotle Onassis

Aristotle Onassis

Greek shipping magnate Aristotle Onassis showed the world the importance of great taste combined with a good tailor (Caraceni of Milan, since you asked) – and just how vital this combination can be to hiding a multitude of sins. He debunked the rumour that larger men shouldn’t wear double-breasted suits and was beaten only by his world-famous wife in the style stakes.

Serge Gainsbourg

One of very few men who could pull off a three-piece suit without a tie or socks, all-round genius creative Serge Gainsbourg made it all look so easy. His bad living – just look at his nonchalant way with a cigarette – only compounded the coolness of his style.

Jack Kerouac

jack kerouac

Embracing workwear as both a functional uniform and a sly two fingers to nonconformity, American writer Jack Kerouac epitomises the understated, unquestionably cool and endlessly imitated style of the Beat Generation. the essential summer style icon.

Peter Beard

peter beard

The sadly recently passed Peter Beard perfected the rugged look like no man before or since. Whether chasing elephants in Kenya or photographing monkeys on his East African ranch, Beard never looked anything less than suave. The epitome of safari-chic.

Robert Redford

Redford did what so many have tried and failed to do. He took casual basics (think khakis, jeans and loafers) and found his own way to dress them up or down – but always look like the best-dressed man in the room. He also had quite the way with a three-piece suit.

Marlon Brando

Brando wore the clothes, he never let the clothes wear him. Whether it was a plain white T-shirt – which he wore to global fame – or a traditional suit and tie, everything Brando put on was instantly imbued with his inner cool. And for that, we salute him.

Clint Eastwood

Legendary American actor Clint Eastwood’s attitude has always been his best accessory. As well as proving that tweed jackets could be worn with almost anything, as long as the cloth is good enough, he has also showed that age doesn’t need to be a defining factor when it comes to style. His later life penchant for patterned shirts and tailored chinos have resulted in some of his best looks.

John F. Kennedy

American president JFK was unapologetically preppy and we loved him for it. While always strictly in a suit for formal work occasions, his off-duty wardrobe of G.H. Bass loafers, cashmere sweaters and pastel shirts is a lesson in casual spring dressing. If ever at a loss for what to wear when at sea, we look to him.

Marcello Mastroianni

Actor Marcello Mastroianni -widely regarded as the country;s biggest star of all time – brought the master craftsmanship of Italian tailors to the masses. Along with his British and American silver screen counterparts, he set the tone for mid-century men’s style and the pure white suit he sports in the closing scene of La Dolce Vita lives on as one of the finest pieces of tailoring in film history.

Michael Caine

One of Britain’s greatest rages to riches stories, Michael Caine has always showed the power of a great wardrobe and well-chosen accessories for transforming a person. Widely regarded as one of the best-dressed men of 1960s London, his style continues to inspire today.

Yves Saint Laurent

Before Karl Lagerfeld’s leather gloves and Anna Wintour’s bob, it was Yves Saint Laurent’s thick framed glasses and pin sharp suit that formed the first fashion uniform. Looking back at the style of the legendary fashion designer reminds us there was a time when it was the French (not the Italians) who had the whole relaxed elegance thing so sartorially spot on.

Duke of Windsor

The British royal family has long been known for their sartorial flair and the Duke of Windsor (formerly King Edward VIII) was no different. Savile Row’s Frederick Scholte was his tailor of choice and, whether holidaying in glamorous locations or on official royal duties, his style can only be described as immaculate.

James Dean

The original rebel without a cause, Dean was able to add an effortless cool factor to anything he laid his hands on, from a leather jacket to a plain white T-shirt. And how could the man that turned blue denim jeans into an American style icon not make this list?

Alain Delon

Alain Delon showed the rest of the world exactly what French tailoring could do for a man back in the 50s and 60s. And we can think of few men who have ever looked better in a trench coat.

Inspired? Here’s how to dress like Steve McQueen…

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The Gentleman

The Gentleman

The Gentleman is the mercurial editor-at-large of the Gentleman's Journal.

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