My friend, the gloriously talented stylist Yohana Lebasi, texted me the other day and asked for a funny logo, merch-y hat to wear for vacation. I initially balked at giving any info. Usually, I advise against buying anything solely for a trip. To boot, I’d say to hold off on buying any form of merch.

After all, the idea of merch can feel fleeting and like too much of an expensive way to show allegiance to something, which you will end up not wearing. But the baseball cap lives in limbo. At its core, a hat is an item that can go with anything, whereas a shirt or sweatshirt is already the bulk of an outfit. In memorabilia form, the hat is a whisper of kitschy fun for the dome; a wink to the rest of the look! Plus, the baseball cap can add levity to even the most megawatt outfits. Look to the early ‘90s Carolyn Cerf de Dudzeele-styled Vogue editorials, where the models were drenched in fat furs with a humble baseball cap on top of their luscious blowouts.

Even the most ostentatiously embroidered cap can be a no-thoughts-necessary purchase: It typically runs anywhere from $15 to $150. On the lower price end, this sort of buy is more low-stakes than, say, coughing up for a designer bag that everyone already has. Plus, the fact that the hat’s design nods to something specific, like a film or a place, means that the accessory boasts a one-of-a-kind factor. It means something to you—and perhaps other people. A Ralph Lifshitz hat? That signals you know that Ralph Lauren’s surname was originally Lifshitz. A Madonna “Drowned World” cap? Hello, it’s the only hat from her Ray of Light era!

The merch-y baseball hat is also the way to get a subversive slice of the bigger, more expensive picture. It’s like getting a martini at a hotel bar instead of splurging for the suite. In quite literal terms, it’s like saying: No, I cannot afford to stay at The Ritz, but I can purchase a cheeky $18 “vintage Ritz Carlton South Beach” dad hat that has already been sun-bleached by a monied old geezer who laid out by the pool every Christmas. He put the work in for us!

As we delve deeper into the relentless argument of how doing things, being active, and having hobbies funnel into the idea of “good taste”, the merch-y baseball cap might have legs. It’s a nod to whatever the wearer is into. After all, more than ever, people are writing about where they are eating, what they are watching, and where they are going—or hope to be going. The days of people mindlessly droning on about what designer pieces they bought feel numbered. Even shopping for vintage feels like fast food; punch a term into the search bar and mindlessly tear open the package three days later. It’s times like these when an old Basic Instinct hat is invaluable; a little visual gesture that you know Catherine Tramell wore white slingbacks during her interrogation scene. An obsession is priceless.

Also, a pro search tip from the queen of eBay,

My list of sickeningly amazing merch-y baseball caps from mononym superstars, films, and a hint of fab NYC skylines…!