The defining icons of gentlemanly style

Somewhat ironically, achieving timelessness takes time. Some of the most stylish gentlemen came to prominence before the advent of technicolour, yet they seem to step from the celluloid on to the pavements of today, their influential dress-sense still emulated after 50 or 60 years. From Cary Grant to James Dean – the golden boy to the broody countercultural icon – these are the men still emulated around the world today.

Cary Grant


Born Archibald Leach, Grant offset the difficulties of his childhood with a little blind faith in the American dream. Indeed, he was one of the precious few for whom it was not hollow: crossing the Atlantic to make his way in America, Grant became one of the greatest leading men the film industry has ever seen. Many men still look towards Grant for suiting inspiration, yet it may come as a surprise to discover that many of his suits were in fact ready made, and often 10 or 20 years old. Even in his prime, Grant stood as proof that style remains distinct from fashion and its fickle trends.

Alain Delon

alain delon

One of the great stars of 1960s European cinema, the youthful Delon cultivated a broody and troubled persona that led to him being hailed as the French James Dean. Famously rejecting an offer from Hollwood in favour of the French film industry, Delon nevertheless achieved international renown, gaining a distinct following as far afield as Japan. Perhaps most at home in a neutral toned blazer, pale trousers and loafers, Delon had a profound influence on men’s Riviera style.

Sean Connery


Snagging the leading role in one of the most successful film franchises of all time has endowed Connery with a certain mythic quality. If the stories are to be believed, it was Dana Broccoli, wife of Dr. No. producer Albert Broccoli, that convinced her husband that Connery was the man he was looking for, stating as her argument that Connery moved “like a panther”. Connery excelled at wearing the refined menswear staples with confidence – outfits in which very detail works towards the overall impression. Here, for example, it is the length of his shirt cuff showing beneath a turned-back satin sleeve.

Michael Caine

English actor Michael Caine, originally Maurice Micklewhite, the star of films like 'Alfie' and 'The Ipcress File'. (Photo by Stephan C Archetti/Getty Images)

Image: Getty Images

Like lifelong friend Sean Connery, Caine came from a working class background, growing up in the London Borough of Southwark. Coming to prominence at a time when cinema was dominated by actors with the even-toned elocution of public schoolboys, his trademark cockney accent made him a somewhat controversial figure. Caine, however, made this his own; always sharply turned-out but with a hint of rakishness, he retained an aura of one who exists beyond stuffy establishment rules.

Steve McQueen


Taking aim at stardom: Steve McQueen in 1962. Image: John Dominis 

His eyes hidden by his trademark Persol sunglasses as he cradles a cocked .44 Magnum, the McQueen of Dominis photograph seems the archetypal anti-hero. With an anti-authoritarianism that extended beyond his screen roles, The King of Cool was famed for wearing denim, t-shirts and Harrington jackets – the key pieces of off-duty style that still make up men’s wardrobes today.


Dean, the broody poster boy of 1950’s. Image: Getty Images

James Dean was only 24 when he smashed headlong in to a swerving car while driving his beloved Porsche Spyder. The fatal accident cut short a deeply promising career, yet Dean achieved a form of immortality as the poster-boy of teen rebellion – one who would remain ever-young. Famous for his subversive 50’s countercultural dressing, Dean replaced suits and collared shirts with t-shirts, leather biker jackets and his trademark red Harrington jacket.

Salvador Dali


Salvador Dali and David Bailey in 1972. Image: David Bailey

A man who basked in sensationalism, Dali had a self-professed love for “everything that is gilded and excessive”. With his elongated moustache-tips tuned like antennae to the world around him, Dali had a bold and fittingly eccentric sense of style. He would mix thickly striped suits with wild, kaleidoscopic ties and a long cape – choices that bespoke of a man distinctly aware of the power of image.

David Bowie

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David Bowie photographed by Helmut Newton. Image: Helmut Newton

Moving through styles with encyclopaedic self-reinvention, Bowie’s used style as a form of raw self-expression. Ziggy Stardust, Aladdin Sane, The Thin White Duke – Bowie seemed to treat himself like a shop-front mannequin, a vessel to be stripped and re-clothed with each new persona. Risqué and androgynous, it was a style that could only be achieved by someone with the charisma of Bowie, but remains as an important reminder that men too can subvert the norms of dressing.

The Duke of Windsor


A controversial but eminently stylish Royal, the Duke of Windsor was renowned for his modern, even avant-garde approach to dress. While his position called for the stiffest formality, The Duke believed that smartness should  should not be worn at the expense of comfort, favouring soft-collared shirts at a time when the stiff, starched collar reigned supreme. A man of short stature, he nevertheless wore large checked suits with aplomb, making good use of his tailor in order to give the impression of an elongated frame. With a reign that lasted less than a year, he may have had little effect on the politics that shaped his country, but he had an undeniable influence on the way his one-time subjects dressed.

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