How I Learned to Wear a Baseball Hat

Like most things that I take seriously in life, my novelty-baseball-cap collection started out as a joke. In 2019, a friend and I went to see the Broadway revival of Harold Pinter’s 1978 play, “Betrayal,” about a trio of friends caught in a brutal love triangle. The play is an acidic bummer, where everyone swills chilly drinks and spits out chilly lines and nobody ends up happier than when they started. As we shuffled out of the theatre afterward, my friend let out an audible “Oof.” Then she added, “How hilarious would it be, though, if you bought the hat?” The hat in question was a souvenir item for sale at the back of the theatre. Go to “Hamilton” or “Lion King,” and you’ll find mugs and pennants and pins and tees and totes. Not at “Betrayal.” Perhaps in keeping with the spare devastation of Pinter’s writing, and also with its inherent absurdity, the merchandise here consisted only of a black baseball cap with the word “Betrayal” printed on the front in white embroidery. It was a ridiculous hat—someone probably designed it in an afternoon, perhaps in ten minutes, maybe even in ten seconds. Best twenty dollars I spent that year.

At first, I wore the “Betrayal” hat solely on bad-hair days, when my bangs just wouldn’t lay right. But soon I started putting it on most days. The hat became a small conversation piece, a wee wearable icebreaker. Strangers would say, “So, who did you betray?” or ask whether I was sporting the name of a cheeky new fashion line they had never heard of. Nobody ever brought up the Broadway show, because, well, why would they? The revival was more or less a splashy excuse to let Tom Hiddleston ooze gravitas in between Marvel movie gigs. It barely had fans, let alone stans.

Inspired by the bizarre power of the hat, I bought another one, from the cult-popular online store Super Yaki—a blue denim number that reads “A Film by Nora Ephron” in typewriter font. Where the “Betrayal” hat makes people confused, the Ephron one makes them rhapsodic. People love to talk about Ephron movies, and the hat serves as an open invitation for them to do so. Ephron herself preferred floppy, formless fisherman’s caps to match her baggy tailored pants and crisp, white poplin shirts. Her look was always polished but comfortable, a little bit Diane Keaton and a little bit Katharine Hepburn; she left the baseball-cap wearing to colleagues such as Steven Spielberg, who seems to never set foot on a set without one. Yet, strangely, wearing the Ephron hat made me feel as if I’d inherited a bit of her pulled-together sparkle. There is something about topping off a blah jeans-and-sweater combo with a well-fitting, well-loved cap that makes you instantly feel adventurous and ready for the day, like you’re a tourist in your own neighborhood.

I know I probably sound like the last person on Earth to discover fun baseball hats. Sports fans know this. Anyone who has been to a Lids store in a mall knows this. Anyone whose uncle went on a trip and brought home a silly souvenir hat that says something like “Rhode Island Hot Weiners!” knows this. Judah Friedlander on “30 Rock” knew this. But I was a late bloomer to ballgame-related millinery. In my youth, my mother used to tell me that I had a knack for pulling off hats. As a result, I lost a lot of my best years trying to make doofy and unflattering headgear work—felted fedoras, vinyl visors, bucket hats with giant fake sunflowers on them à la Blossom, overly formal cloches that were more suited to a minor British royal, pastel cowboy hats, twee berets, terrible neoprene trucker hats with mesh backs that made my head look eight feet tall. In my adult years, I’ve retained an affection for certain ostentatious hats deployed in moderation—a faux-fur Cossack-style cloud puff on the coldest day of the year, or a big-brimmed sun hat at the beach. But it’s the ball caps that have worked their way into my daily routine. Pulling one on in the morning feels strangely comforting. It conforms to your scalp, and, when you cinch the back strap tight, it gives your skull a warm embrace. With all due respect to flat-brim devotees, I like my brims deeply bent so that they resemble the dreamy arch of a rainbow. Good ball caps are one of those rare articles of clothing which get better and better over time. They turn buttery and soft in your hands. They fray a bit at the edges and look all the better for it.

The Internet is awash in novelty baseball hats. A Babar cap from the preppy brand Rowing Blazers. A one-off neon collaboration between the sporting brand Champion and the chic-purse designer Susan Alexandra. A hat festooned with cherubic Fiorucci angels. An on-the-nose hat for bad-hair days. A hat that reminds you to hydrate. A hat that says “For Your Eyes Only,” from a buzzy eyelashes brand. A cap that tells your friends that you are a bit emotional this week. A French hat with a bunny on it, which has the slick European feel of Formula 1 racing. A hand-painted Balenciaga cap, which is so ugly that it comes around the horn again and becomes almost glorious. A hat that proclaims, à la Nicole Kidman before every AMC film, “Somehow Heartbreak Feels Good in a Place Like This.” Practically every museum and literary magazine now hawks a Dad Cap as merch for the kind of people who don’t think of themselves as buying merch: there’s The Drift hat, the Met hat, The Paris Review hat, and, yes, even this magazine’s yearly softball hat. But the joy of being a Hat Person lies not in buying the It Hat of the moment but in seeking out strange, defunct caps on eBay when you can’t sleep, guided by whatever keywords spring to your mind. It lies in finding the caps that give you and you alone pleasure, and then sharing that pleasure with anyone who cares to glance at your head.

In the past year or two, I’ve racked up a number of new specimens to hang beside my “Betrayal” and Ephron caps. I was thrilled recently to find a colorful hat covered in hot-air balloons, commemorating the Albuquerque International Balloon Fiesta, an event I attended yearly as a child. But most of my picks are pop-culture references, mostly from the nineties, a kind of Dadcore nostalgia that just feels right to me at the moment. I found an official “Seinfeld” hat that still had a sales tag from the NBC store. I found a hat that simply says “Friends” in the font of the TV-series logo. I found a hat with a brown-suede brim from the original run of “Les Misérables” on Broadway. In perhaps the nadir of my frenzy, after realizing that the 1995 rom-com “French Kiss” was not available to stream, I had a custom hat made through an online printer, reading “Let Us Stream French Kiss.” My favorite hat might be a cream-colored vintage one from the storied Upper West Side grocery store Zabar’s, which I paid far too much for on the online secondhand marketplace Poshmark. I don’t live on the Upper West Side, or even get up to Zabar’s that often, but it gives me joy to chat with strangers about the quality and affordability of the store’s coffee beans. Last month, I bought another exquisitely inane hat inside a theatre lobby, at the troubled Broadway revival of “Funny Girl.” It says “Hello Gorgeous” in a banana-yellow font, and I wear it on the days I feel most unkempt. I didn’t love the show, but the hat? It’s a star. ♦