I have lots and lots of dad caps — dozens, perhaps 60 — which is funny, really, because I’m not a dad and I’ve always had a famously good hairline. But where some men would like to be defined by their shoes, their watch, their surname, their school, their degree, their job, their backhand, their bank balance, their abs, or their Instagram following, I’d like to be judged by all of these things, and also my caps. A cap is whimsy without wackiness. It is understatement without slovenliness. It is referential but never gimmicky. It is preppy but inclusive. It says sportiness, but — and this is crucial — it isn’t made of Lycra.
With the right sunglasses, you look like you might be famous in an airport. With the right tennis racket, you look like you might be about to play tennis (which is never not chic.) I hoard them, prize them, seek them out, pinch them, bid them up on eBay, and weep over them when they are lost (somewhere, in the Gare de Bordeaux lost property bin, there is a gorgeous vintage Rolex sailing cap with my sweat forever inside it.) The peach of my collection — or the top hat, if you will — is a green-and-white number from a Bear Stearns golf day in 2007, just a few months before the investment bank got significantly fubar’d by its own folly. The back of the cap reads ‘ABOVE PAR’, which Bear demonstrably wasn’t. You couldn’t make this stuff up, but you can wear it to the pub.
Which brings me to the great irony here. You never really want a new cap, because a second-hand cap — ideally one produced for some esoteric, niche event and sponsored by a defunct aperitif maker, perhaps — always tells a much better story. But if you have to start afresh, you should plump for one of these, which are delicious in their own right. Hats off.
For collegiate irreverence...
Hark at the bottle green hue of this proud, preppy corduroy number from Rowing Blazers, who seem, sometimes, to be single handedly keeping this fine art alive. Timothée Chalamet’s been spotted stateside in this puppy, which you may or may not want to hear. We just like the detailing — specifically that hand-embroidered wire bullion badge.
Rowing Blazers Derry Bones Corduroy Dad Cap, £60, rowingblazers.com
For some nantucket nattiness...
A pale, sun-faded yellow number here, which speaks of the East Coast, the sea air — and grilled meats in the evening breeze, for some reason. A sunny delight — which isn’t a reference Sir Ralph Lauren is likely to understand, and quite right too.
Polo Ralph Lauren Stretch-cotton twill ball cap, £49, ralphlauren.co.uk
For sun-kissed simplicity...
The Australians are about 15,000 miles closer to the sun, by all accounts, than any other nation on earth. So it’s only natural that their very finest tailor (and one of the best over here, too, if you ask me) should make a sun cap of such simple, sportif beauty. Glorious.
P Johnson White dad cap, £POA, pjt.com
For peak 1980s prep...
Are You A Preppie? Well, are you? That’s what the famous poster — produced in 1979 for college campuses up and down the East Coast, and now the inspiration for this jaunty headpiece — asked of those around it. The Preppie Scourge was upon them then — a romping, chortling, ruddy-cheeked, green-polo’d, moth-eaten, old-moneyed set, complete with premature gout, questionable trousers and plenty of sporting war stories. Simpler times. (And better caps, too.)
Rowing Blazers Are You A Preppie cap, £40, rowingblazers.com
For tennis-inflected fun...
Prince was once the prince of tennis brands — a stately stalwart of 1980s court style, and the purveyors of some bloody useful tennis rackets on the North Oxford mixed doubles scene in the late nineties, if memory (and all those framed photographs above my mantelpiece) serve me correctly. Then the brand fell out of favour for a while. But now it’s making its way back — and this collaboration with Zara, of all people, is some understated, thickly-embroidered tennis club chic of the highest order.
PRINCE VS Zara cap, £17.99, zara.com