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The best dressed men in Britain 

29 August 2018

When it comes to the best dressed men in Britain, competition is fierce. Year after year, a new icon graces us with his presence and we’re forced to decide who most appropriately fits the bill. We’ve drafted in menswear style writer, Josh Sims, to teach us the ropes when it comes to Britain’s most dapper.  


Anthony Eden 

It’s not often that one associates a British politician with stylish dressing. That wasn’t the case for Anthony Eden, who became Prime Minister in 1955, whose snappy style provoked no shortage of sniping. Mussolini would call him “the best-dressed fool in Europe”, with the Earl of Crawford saying that he was “as vain as a peacock”. Regardless of those who didn’t want to believe it, he was influential in matters of national policy and style alike. Apparel Arts, a style magazine of the time, noted how his love of a signature white linen waistcoat “makes it assume importance as a distinctly promising item for the summer months”. His preference for a black homburg hat even saw the style renamed ‘the Eden’. And it’s still called that today.

Michael Caine

Caine’s reputation for style was arguably founded in one photo: the black and white David Bailey portrait that, in part, defined the 1960s. Here was a leading man despite, for the first time, being blonde, a wearer of spectacles and working class. “I created my own image - and it worked,” he said. It was his background, however, that made him stylish in a way that didn’t feel part of the conservative establishment. It was still suited –  but cool and continental. In film after film; ‘The Ipcress File’, ‘Get Carter’ and ‘The Italian Job’, to name a few, the influence of a good tailor was never far away.

George Best

The association between footballers and fashion is often thought of as being a modern phenomena. But George Best invented it, half a century ago. The man dubbed ‘the fifth Beatle’ for his influence on pop culture, Best not only loved fashion, he opened his own chain of menswear shops and hair salons, and was recruited for football’s first ever fashion-related endorsement deal. Fashion was, of course, all all part of his high living. “In 1969 I gave up women and alcohol - it was the worst 20 minutes of my life,” he once quipped. Best could even start trends on the pitch: he is said to have been the first footballer to wear his shirt hanging outside of his shorts.

Cary Grant

The Hollywood star often proclaimed his puzzlement as to why “well-meaning” groups often voted him the best-dressed man of the year, because, he said, he never considered himself well-dressed, never made any effort to ensure he was wearing fashionable clothes and was most typically seen in a role. “Everybody wants to be Cary Grant,” he noted. “Even I want to be Cary Grant”. But that was his secret: he was a die-hard fan of classic clothes such as the likes of dark, slimline suits, white shirts and knitted ties.

The Duke of Windsor

 There was a time when the clothes that royalty wore defined fashion: all trends filtered down from the very top of society. At the top was once Edward VIII, later the Duke of Windsor, a man who loved clothes to the point that he worried the public would consider him no more than “a glorified clothes-peg”, as he put it. He effectively invented the modern dinner suit ; made midnight blue its classier choice of colour; he re-invented tartan; he wore pastels when most men considered colour to be feminine. Being King, briefly, made him a unique individual – but he was that via his wardrobe, too.

Words by Josh Sims, images by Getty

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