THE JOURNAL
Mr Steven Spielberg in Beverly Hills, 1 May 1990. Photograph by Ron Galella Collection via Getty Images
Some years ago, I was late for the wedding of an old friend. Properly, panic-inducingly, palm-sweatingly late, for a service at which I was due to give a reading. Seconds after I rushed up the aisle, past a room full of tutting guests, the bride rounded the corner and made her procession. As she saw me, she smiled, and then scowled.
“What,” she hissed, “have you got on your head?”
And that’s how I learnt not to wear a baseball cap to a wedding.
For the past decade, I’ve worn a cap almost everywhere. At business meetings, dinner parties and to meet my boyfriend’s parents. Come rain or shine, in a suit or shorts. Over years of collecting, my inventory of headgear has expanded beyond a drawer, and now fills a trunk with some overspill.
I’m not sure where it began – certainly, not from any need for concealment. My head is mercifully free of lumps, bumps or anything to give pause to a phrenologist. And I have – so far, at least – no bald patches, and little recession in my hairline. In fact, for the past several years, I have bleached my hair with militant regularity, spending considerable time on achieving the perfect shade of blonde, before thrusting it unceremoniously beneath a cap.
It’s become a security blanket, of sorts: similar, I suppose, to women who don’t feel “dressed” without lipstick on. And, certainly, it eradicates any concerns about bad-hair days. But beyond that, it’s a balm to my persistent, low-burning anxiety about appearing overdressed, or – the eternal millennial concern – of “trying too hard”. I’ve lived most of my life with the recurrent fear that I’d turn up to work, or a social event, or a funeral, and look like I’ve put too much effort in. It takes little more than someone seeing what I’m wearing and saying, “Ooh, you’ve made an effort,” to bring me to collapse. Mentally, I never grew out of the hoodie-wearing, corner-skulking teenager of the early 2000s.
“It’s become a security blanket… It’s a balm to my persistent, low-burning anxiety about appearing overdressed, or – the eternal millennial concern – of ‘trying too hard’”
Needless to say, I’ve never subscribed to dandyism, or the TOM FORD ideal of dressing as a power flex. Frankly, I’m not cut out for it. So, for those of us who can’t manage the perfectly pressed, no-hair-out-of-place school of dressing, there’s a relief to be found in willingly looking a little scruffy, and in throwing an otherwise “proper” outfit into more louche territory. And there’s no easier way to do that than by chucking on a baseball cap.
Allow me to make my case: consider Mr Robin Williams, a long-time icon of charmingly dishevelled dressing, in a cap-and-cardigan combination in Good Will Hunting. Or Mr George Michael, in his early-1990s prime, in an LA Raiders cap and a biker jacket. Not to mention the king of “caps with everything”, Mr Steven Spielberg, who melds them so perfectly into his day-to-day style that he almost looks odd without one. True, they’re not classical style icons – but that’s the point. In their casual, thrown-together approach to dressing, they project an ease and confidence, which I find far more aspirational.
Mercifully, it’s backed up by what’s happening in fashion, too. Simple, wear-anywhere caps have cropped up in collections of brands at every end of the “smart” spectrum, from Brunello Cucinelli to Off-White. And at last week’s Pitti Uomo trade fair in Florence – usually an event dominated by a classically Italian sophistication – trucker caps emerged as an unlikely sensation, worn with everything from linen tailoring to breezily cut camp-collar shirts.
A few caveats: despite my belief that a cap can work anywhere, there is a spectrum of acceptability when it comes to style. The best caps should have unobtrusive branding, and are best in muted tones. But beyond colour, print or logos, the most important differentiator between a “smart” cap and an “unsmart” one is shape. Simply put, the safest bet is a more rounded style, in an unstructured fabric that won’t sit too high on your head. My current favourite, which has barely left my head in months, is a six-panel, curved-brim style from the Danish brand NN07, in a pleasingly minimal navy nylon. I’ve found that it works with scruffy and smart outfits alike.
Would I wear a cap to my own wedding? Most certainly. After all, dressing for those kinds of events works best when it feels like an expression of natural style. If that day comes around, I like to think I’d be in a loosely cut suit from Lemaire, topped with a borderline-ancient denim cap from A.P.C. that’s one of my most prized possessions. At the very least, on that occasion, no one will be able to tell me off for wearing it.