A few years ago, I was late for an old friend's wedding. Late, so late that it caused me to panic and sweat, for a service where I was to do a reading. Seconds after I rushed down the aisle, past a roomful of grumbling guests, the bride turned the corner and made her way through the procession. When she saw me, she smiled, then scowled.
"What's on your head?"
And that's how I learned not to wear a baseball cap to a wedding.
For the past ten years, I've worn a cap almost everywhere. To business meetings, to dinner parties, and to meet my girlfriend's parents. Rain or shine, with a suit or shorts. Over the years of collecting, my headwear inventory has grown beyond a drawer and now fills a trunk, with a few overflowing.
I'm not sure where this collection came from—certainly not from any need for concealment. My head is mercifully free of lumps, bumps, or anything that might give a phrenologist pause. And I have—so far, at least—no bald spots, nor any recession in my hairline. In fact, for the past few years, I've bleached my hair with militant regularity, spending considerable time achieving the perfect shade of blonde, before unceremoniously burying it under a cap.
It's become a kind of security blanket, much like women who don't feel "dressed up" without lipstick. And, of course, it eliminates any worries about moody days. But beyond that, it's a balm for my persistent, low-intensity anxiety about looking overdressed, or—perennial millennial preoccupation—"overdoing it." I've lived most of my life with the recurring fear of arriving at work, a social event, or a funeral and looking like I've tried too hard. All it takes is someone to see what I'm wearing and say, "Ooh, you made an effort," for me to collapse. Mentally, I've never moved beyond the hoodie-wearing teenager lurking in corners in the early 2000s.
Needless to say, I've never subscribed to dandyism, nor to the TOM FORD ideal of dressing like a power flex. Frankly, I'm not cut out for it. So, for those of us who can't dress perfectly pressed and hair-free, it's reassuring to purposefully look a little scruffy, and throw an otherwise "okay" outfit into more sleazy territory. And there's no easier way to achieve this than by donning a baseball cap.
Let me make my case: Consider Mr. Robin Williams , a longtime icon of charmingly disheveled dressing, in a cap-cardigan combination in Good Will Hunting . Or Mr. George Michael , in the early '90s, in an LA Raiders cap and biker jacket. And then there's the "cap-with-everything" king, Mr. Steven Spielberg , who incorporates them so seamlessly into his everyday style that he almost looks odd without them. Granted, these aren't classic style icons, but that's the point. In their casual, off-the-cuff approach to dressing, they project an ease and confidence that I find far more inspiring.
Fortunately, this is confirmed by what's happening in fashion, too. Simple, wear-anywhere caps have been popping up in the collections of brands at all ends of the "smart" spectrum, from Brunello Cucinelli to Off-White . And a few weeks ago, at the Pitti Uomo trade show in Florence—an event usually dominated by classic Italian sophistication—trucker caps made an unexpected splash, worn with everything from linen suits to casually tailored camp-collar shirts.
A few caveats : While I'm a firm believer that a cap can be used anywhere, there's a spectrum of acceptability when it comes to style. The best caps should have discreet branding and are ideal in neutral tones. But beyond color, print, or logos, the biggest differentiator between a "smart" and a "not-so-smart" cap 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 favorite, which has barely left my head in months, is a six-panel, curved-brim design from Danish brand NN07 , in a pleasingly minimal navy nylon. I've found it pairs just as well with scruffy outfits as it does with smart ones.
Would I wear a cap to my own wedding? Most definitely. After all, dressing for this kind of event is most effective when it's about expressing effortless style. If that day ever comes, I like to think I'd wear a loose-fitting Lemaire suit, topped with a denim cap from APC , which is one of my most prized possessions. At least on this occasion, no one will be able to criticize me for wearing it.
Text by Mr. Rob Nowill
Photo of Mr. Steven Spielberg in Beverly Hills, May 1, 1990. Photograph by Ron Galella via Getty Images.
