Hat tricks: how to look good in a hat

Brad Pitt in Thelma and Louise; Pharrell Williams wears Westwood; Mad Men's Don Draper (Jon Hamm); David Beckham

So you want to wear a hat but you’re worried about looking more ‘Bugsy Malone’ than ‘Don Draper’. Milliner Stephen Jones shares his tips with Stephen Doig

Brad Pitt in Thelma and Louise; Pharrell Williams wears Westwood; Mad Men's Don Draper (Jon Hamm); David Beckham
Brad Pitt in Thelma and Louise; Pharrell Williams wears Westwood; Mad Men’s Don Draper (Jon Hamm); David Beckham

David Beckham’s particular style panache hit headlines again this week, when he left the Arts Club after his wife’s 40th birthday in an elegant chocolate brown hat; not quite a trilby, not quite a fedora, a sort of Pharrell-lite, but handsome nonetheless.

It was a brave move, because hats can be cruel mistresses. It’s easy to be seduced by the sartorial connotations of hats – Don Draper in his fedora, tilted just so, Sean Connery posturing for Louis Vuitton in a crisp panama. Even Pharrell in his vintage Vivienne Westwood crown has a certain swagger. But all too easily the result looks more ‘regional amateur dramatics production of ‘Bugsy Malone’ than ‘Errol Flynn elan’.

It’s a predicament I’m all too familiar with, after an unfortunate debacle with a Marni cadet-style cap that I thought might – in my misguided youth – make me look faintly Soviet and cool, like I’d just founded a Berlin electronica movement. It didn’t. I looked like Blakey from On The Buses.

There was a time when a certain calibre of gentleman would know exactly what hat suited his social mores; the start of the ‘season’ would call for all manner of millinery musts, from stately top hats in glossiest black, handsome cathedrals of felt and ribbon, to regatta-ready boaters, as merrily English as Pimms and strawberries.

One man who’s watched the ebb and flow of hat trends come and go is Stephen Jones, the master milliner whose hats have adorned the heads of the world’s most stylish men, including Mick Jagger and Johnny Depp, and graced the catwalks of Christian Dior and Louis Vuitton. What are his tips on how to carry off the trickiest of head attire with aplomb?

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