For men, summer hats are a tricky thing

Among the things I have inherited from my late father is a robust attitude to hats. He wore them only under very special circumstances, and those circumstances were two: fishing — in which a lichen-green number adorned with the odd fly was both handy and fitting — and going away for your summer holidays.

The hat on a man, in civilian life, is usually a thing to be regarded with suspicion. Bowlers have gone the way of the waistcoat fob watch. Flat caps are for farmers and hipsters. The extravagantly brimmed felt fedora, as worn by would-be raffish literary men in late middle age, tends to reek of vulgar self-advertisement. And hats while driving a car — accompanied, perhaps, by leather driving gloves on a Sunday-afternoon “spin” — are the grossest affectation. “Prat in a hat,” my old man would mutter when he found himself stuck behind one on the summer lanes of my childhood.

That rhyme is to be borne in mind. Few are the men who can consistently carry off a hat in civilian life. The list is limited, as far as I’m concerned, to Indiana Jones (fedora), Del Boy Trotter (flat cap), Malcolm McDowell in A Clockwork Orange (bowler) and Benny from Crossroads (beanie) — and be it noted that all of these are fictional characters.

My austerity on this front is in part the result of an early humiliation. Inspired by the first of these exemplars, I asked for a fedora for one birthday as a pre-teen, was given one, and still now blush to imagine how a scrawny 11-year-old wandering through Dorking town centre in the late 1980s in a fedora would have looked.

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But a straw hat for summer, paired with a clean open-collared white shirt, knee-length shorts and flip-flops, is a pleasing thing. For those of us with the sort of optician’s prescription that prevents us wearing contact lenses — and who neither want the expense of prescription sunglasses, the creepy look of photochromatic lenses (the sort that darken in the sunshine) or the unsatisfactory clip-on, flip-down types — a broad-brimmed hat is essential in bright sun.

Endless Joy floral-print Tencel-blend twill bucket hat, £120,
New Era 9forty New York Yankees woven cap, £30,
New Era 9FORTY New York Yankees woven cap, £30,

For the past several years in my house, it has been the infallible sign of summer that I reach down from the top of the wardrobe the straw hat that I bought from a street market in Cuba in, gosh, 2009. It cost me $5, has travelled all over the world and — though the black fabric hatband is frayed and faded, and the salt-tides of sweat have made little maps on the inner rim — is in astoundingly good shape.

It’s the sort of hat that people will tend to refer to as a Panama, though my old dad insisted that a proper Panama hat should, like his, have a seam on top and be rollable so that you can put it in a suitcase. Mine never goes in a suitcase — but it has perched happily atop my carry-on baggage in countless overhead luggage compartments and sailed through customs aboard many a trolley.

It not only signals summer but it participates in all sorts of summer activities. You can take pleasure in the affectation of raising and lowering it slightly in greeting. You can practise the Michael Jackson-style rolling-up-your-arm manoeuvre to put it on your head in order to impress your children (angle hat downward, grasp the rear side of the brim lightly in your fingers, roll and flip). It makes a handy repository for keys and wallet when you go swimming. And, of course, it covers your whole face more comfortably and airily than anything else when you have in mind an afternoon snooze on a sun lounger.

Warnings against male hat-wearing notwithstanding, my more style-minded colleagues inform me that hats are very much galloping back into fashion for the male of the species — and doing so just in time for the summer. Selfridges reports that hat sales are up 80 per cent from 2019. If you don’t want to look like Holiday Dad, in other words, there are acceptable alternatives.

Oddly, the hottest item du jour — or, as fashion folk put it, “the key shape” — is actually the good old bucket hat, which, to those of us of a certain vintage inescapably connotes Mani (or Reni or Stimpi or whatever he was called) from the Stone Roses and takes us back to a blur of wide trousers and blissed-out vibes and pretending to have been at the Spike Island gig.

Judging by the selection on Mr Porter these days, the bucket hat has come on since I was a lad. I was rather taken, for instance, by a black bucket hat from Endless Joy (slogan: “Free your mind and your ass will follow”) splashed with cream and yellow blooms of epiphyllum, and the Pop Trading Company’s natty and understated take on the style in dark blue corduroy. One’s ravey, one’s navy. Both will roll up and fit handily in your back pocket. Isabel Marant’s mauve-and-lilac Chapeau Haleyh is a handsome thing, I thought — but a little too outré for me to get away with. Fortunately, the admirably unisex nature of the bucket hat means that my 12-year-old daughter will look great in it.

Palm Angels logo-embroidered cotton-twill baseball cap, £155,
Palm Angels logo-embroidered cotton-twill baseball cap, £155,
Pop Trading Company logo-embroidered cotton-corduroy hat, £55,
Pop Trading Company logo-embroidered cotton-corduroy hat, £55,

And then, of course, there’s baseball caps — which come in a dizzying number of varieties, from the practically disposable to something north of £500 (thank you Brunello Cucinelli). And, fashion being what it is, if you’re taken with Celine Homme’s mesh trucker cap you can spend £335 to look like Cletus the Slack-Jawed Yokel from The Simpsons.

For those of us past the first flush of youth, I should say, baseball caps are to be worn, if at all, forwards. Backwards says beef-fed American youth or, worse, Steve Buscemi saying “How do you do, fellow kids?” There’s a definite semiotic divide between the adjustable baseball cap, the non-adjustable baseball cap (cloth all the way round, brim to be bent into an arch) and the mesh-crowned type which says you aspire either to be driving an 18-wheeler through the Nevada desert or opening a cereal café in Hoxton Square. If you don’t bend the brim into an arch, by the way, you’re looking like either a rapper or a South Korean pro video-gamer, both of which are hard looks for middle-aged Anglo dudes to pull off.

For the likes of me, a classic style is, I think, the way to go. I have a proper Yankees cap, non-adjustable, which has had the odd non-baseball-game outing. Palm Angels and Folk clothing, for instance, both do a nice understated one-colour fabric hat without a plastic fastener and with a pleasant curve to the brim. If you’re under 30, though, you can go wild with gaudy ironic appliqué logos and bright colours (example: Central Bookings International’s fun Toytown range).

Still, if all else fails — and, for instance, you leave your beloved straw hat in the overhead compartment when you leave the plane — there’s always ye olde knotted handkerchief.

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