Graham Williams, a 41-year-old solicitor from Hertfordshire, has made hats his signature — not only in his private life but in his professional one, too.
“I work as a lawyer, and the stereotype is that we wear grey suits which are sort of devoid of personality,” Williams says. “One of the things I learned early on in my career is that if I turn up looking like a lawyer, my clients will be scared, clam up and just not speak to me. If I wear something that’s got more personality it breaks down the barriers.”
Williams’ outfits are bold, and the jazziness of his footwear — think zebra-print espadrilles from Dolce & Gabbana and Paul Smith snakeskin winklepicker boots — is surpassed only by the drama unfolding on his head. His hat collection consists of some 20 pieces, including a panama with an embroidered band by defunct hat maker Nadia C, a dark teal fedora finished with a peacock feather pin from British brand Pachacuti and his current favourite, a leopard-print fedora sourced from a stall on Spitalfields Market.
Williams has been qualified for a decade and is circumspect about whether he would have had the confidence to wear hats when he was a fledgling paralegal. “I feel like I’ve proved myself,” he says. “I’ve worked on some big cases over the years, and I’ve established a senior role for myself so I’ve earned the right to wear what I like.”
The popularity of traditional hats such as fedoras, homburgs and trilbies has declined dramatically over the decades. When once any stylish man would have worn a hat out in public, now the act of wearing anything that isn’t a baseball cap, bucket hat or beanie is seen at best as a sartorial affectation, at worst 1950s cosplay. But some men have persisted in wearing classic hats, with a valiant few even managing to make them their signature.
Gareth Scourfield is one such man. The stylist favours neat little skipper caps and trapper hats, which both tie his looks together and, more importantly, keep his head warm when it’s cold. “I started wearing hats in my mid-thirties when I began losing my hair,” he recalls. “At first, caps and hats were a bit like a security blanket — a confidence-boosting accessory — but I soon started to wear them as a style choice as much as a functional one.”
His collection includes a Connolly cord trapper hat with sheepskin side flaps and a waxed broad-brim gamer hat from Barbour, “though I feel a little Countryfile in the latter,” he admits.
Hats can be divisive. Personally, I struggle with baker boys and have a fear of trilbies. Perhaps it’s because such hats are often worn in situations when they’re entirely superfluous; or maybe it’s because the kind of people who wear said hats in 2023 don’t really do so with the conviction or care of their mid-century forebears, which in turn makes them look self-regarding and silly. Either way, hats are challenging to get right.
“Hats are an affectation, and not a good one,” says Alex Bilmes, editor in chief of Esquire. “People who wear them are annoying. I particularly loathe trilbys and fedoras, on men and women. It’s cosplay. You don’t look like Humphrey Bogart. You look like a horse trainer. As for the most commonly worn hat, I’m with The Libertines: ‘There’s fewer more distressing sights than that / Of an Englishman in a baseball cap.’”
Of course, it’s easier to get away with a personality hat if you’re wealthy, handsome and famous, but even then these accessories have the power to divide, as Justin Bieber’s curiously inspired decision to layer a pink trucker cap over the top of his hoodie did last summer. Pharrell Williams’ voluminous Mountain hats are not universally beloved, nor are Brad Pitt’s preferred trilbies.
David Beckham is famously passionate about hats. The footballer is regularly pictured both in the press and on his own social media accounts wearing flat caps, fedoras and baker boys. His success has been mixed. A brown fedora teamed with navy blue separates and a pair of Rayban Wayfarers at the Queen’s tennis tournament in 2017 made him look cool and understated. The voluminous herringbone baker boy he wore for a walk in mid-2020, on the other hand, looked like he’d dressed as the bastard lovechild of Tommy Shelby and a leprechaun for a costume party. A picture Beckham posted of himself on Instagram in May 2020 wearing a wide-brimmed country hat had a comment from his wife stating “the hat looked ok before someone ran it over.”
As challenging as hats can be to get right, some men manage to look elegant in the extreme while wearing them. Veteran restaurateur Jeremy King is the mastermind behind The Wolseley and one of the most beautifully turned-out men in London. He’s also an avid hat wearer, with an array of homburgs, fedoras and panamas in his 21-piece collection.
“My love of hats started in the ’80s when I spent a lot of time in St James and became beguiled by hatmakers like Lock & Co, Bates and Herbert Johnson,” King tells me on Zoom. “I started out wearing trilbies and panama hats. When my wife moved over from America she was incredulous to discover that I owned more hats than her. She kept opening boxes and asking what was in them. One had a homburg, the other had a bowler hat and then another concealed a top hat.”
On the subject of how he manages to wear a hat without looking like Porchie, the late Queen’s favourite horse trainer, King is poetic. “I think it’s the same as when customers get stood up in restaurants. They’re left at the table, they’re by themselves, they’re immensely self-conscious and so they think that others are looking over thinking ‘who’s that poor old Sally-no-friends over there?’. Whereas in fact, people are looking over and saying, ‘that’s so cool, that’s so elegant, that’s so dignified.’” He smiles. “The same applies sartorially, when wearing hats. If you wear a hat today, you need to do so with confidence.”
Another man who makes hat-wearing look effortless is William Gilchrist, a stylist who has worked with the Rolling Stones and Jude Law. Gilchrist can often be seen lounging in a classic panama during the summer months (he is a fan of Yosuzi), and a charcoal grey or midnight blue felt fedora during fashion weeks. His hats work in tandem with the hues present in his outfits, holding the resulting look together with a deftness only a stylist could muster.
“I had my grandfather’s Lock & Co Homburg refurbished,” says Gilchrist, for whom a family member first stirred his hat passion. “I was lucky that we both had rather large heads, so the hat passed on to me. But, like many things in life, it was David Bowie who first turned me on to hat-wearing, and like most things with David Bowie, his look was unattainable.”
In his hats, Bowie looked self-assured and urbane, a serious artist in command of his audience. But how do the rest of us pull them off?
“It’s important to make sure your hats are the right size,” offers Williams, the solicitor. “When I was young, the hats I was picking up and trying on were too small and therefore they perched too high on my head. It just looked a bit ridiculous. Also, if you’re going to wear a hat, you just have to wear the one you want to wear. You can’t care what anyone else thinks.”
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