Four tips to help men find the perfect holiday hat

Certain evocative vignettes are sealed in the annals of men’s style for eternity; Cary Grant, devilishly handsome and impeccable as he exits Claridges, Jude Law as the raffish Dickie Greenleaf in the 1999 film The Talented Mr Ripley, Robert Redford in the 1970s and just about any image or film still of the endlessly debonair Alain Delon in his heyday. And somewhere in their wardrobe arsenal is a hat, a crowning glory to their look. Time was when a gentleman wouldn’t dream of stepping out the door without his hat, whether a fedora tilted just so or a jaunty Panama, but with the increasing casualisation of how men dress the faithful hat has been relegated somewhat.

This is ever more apparent in summer, a time when once cheerful boaters and sweeping trilbys were a prerequisite of “doing the season”, ubiquitous from Wimbledon to Henley. There’s been a curious revival of the bucket hat in recent years amongst Gen Z; the style codes of the OG (that’s “original”, in Zedder speak) 90s festival goers re-imagined by today’s youth. But for a man over 35, they’re a little tricky. Then there’s the dreaded Peaky Blinders aesthetic, with men up and down the country emulating a 1920s Brummie gangster in a flat cap. Baseball caps are obviously ever-present – and handy as a quick fix in the glaring sun – but they can also be rather youth-centric and casual.

So it’s fair to say that all hats are not created equal, but I’ve long admired men who can pull off a great one, gazing longingly at the stylish Pitti Peacocks on trips to Florence’s biannual menswear fair Pitti Uomo as they offset their plumage with an excellent hat. Being a not-exactly statuesque 5ft 10, I’ve tended to steer clear for fear of looking somewhat squat and shortened, especially after an ill-fated foray with a cadet cap in my youth resulted in me looking like Blakey from On The Buses. But there’s something right and proper about a hat that’s appealing, particularly against a holiday backdrop where it acts as a cooling wingman, perhaps alongside an Aperol Spritz and a warm breeze. How do you choose the right one for you though?

Consider the shape of your head

The venerable Lock & Co Hatters – the oldest hatmakers in the world, and a charming in-store experience if you happen to find yourself in London’s St James’ – advises that oval faces are a general everyman shape for a hat, whilst longer faces suit wide-brimmed hats like Panamas to lend a bit of balance. Rounder faces do well to add a hat with definition and structure, by comparison – a pork pie or fedora, for example.

Picking the right one for summer

Tom Stubbs, a men’s fashion veteran who styles the dashing Dermot O’Leary and Greg James, and who tends to wear a chic little beret on occasion, has some advice on hat etiquette (hatiquette?) for men. “I’m convinced that a good Panama hat is an essential protective and stylistic accessory for time in the hot sun,” he said. They tend to look a little incongruous once the sun has gone in though, let alone the twilight gloom of Stansted airport car park once the holiday is over.” Alongside the everyman Panama – which if from a traditional hatmaker is also just a marvellous thing of beauty in its own right – a boater’s a go-to in summer, although it can look a little twee so avoid the full Henley regatta kit and caboodle if you’re wearing it. Flat caps are by no means out but stick to lighter linen variants to avoid the Peaky Blinders connotations.

How to travel with a hat

Be wary of travelling with one, says Stubbs, because wearing it on the plane can seem a little look-at-me; he advises packing your hat and embracing the wear and tear as characterful. “I have also just acquired a Christie’s rollable number for ease,” says Stubbs. My gentlemanly father-in-law tends to travel with his under the arm until his destination side when it gets its moment in the (literal) sun on the tarmac; it’s a rather wonderfully ceremonial way to start the holiday. One general rule of thumb is to avoid versions tied with string under your chin whilst on the go; too much like you’ve taken a wrong turn on your Duke of Edinburgh.

Fine-tune the rest of your look

A hat’s a statement of intent, so a same-same old T-shirt and shorts aren’t going to cut it. Dress up to meet the standards of your hat, even by small degrees; a fresh linen shirt, perhaps with the addition of a foulard if cocktails on the terrazza are calling, and a jacket if you go for a particularly formal trilby or fedora. Stubbs even customises his with VV Rouleaux ribbon; ‘I’ve added a more tonal, wider grosgrain ribbon, tied in a more flamboyant manner than traditional bands.”

As for the cowboy Stetson; it’s a look best reserved for the plains of Wyoming or dive bars of Texas rather than suburban Tamworth. Best leave it to Willie Nelson.

Try these...

Straw Panama hat, £295, Lock Hatters

Bailey Pork Pie hat, £64.95, Hats and Caps 

Sammy linen flat cap, £39.95, Borges and Scott

Boater, £33.95, Jaxon & James