I’ve got a Yankees cap on my dresser as we speak that has earned its citizenship. It’s been with me longer than some relationships I’ve been in, and I’m willing to bet it has more stamps in its passport than my father. Navy washed-out-to-a-store-bought-grey colour, perfectly curved brim (it took me two years to find the right one – I’ll get to brim curvature later), faded logo that shows age but isn’t threadbare – trust me when I say I know what a good used cap looks like.
I shelled out 20 dollars to a bartender in Montreal to mail it to me after I left it there following one of many forgettable weekend trips. My girlfriend at the time told me it was my security blanket. Ouch.
Surprise: She wasn’t wrong. Caps.

We don’t talk about caps like we do other quintessential American wardrobe staples.
Raw denim? People write think pieces. Classic leather jacket?
Comments under think pieces. But caps? Everyone has a cap.
Everyone wears them. Caps are as American as baseball, sure, but they’re also so ubiquitous that we stop and think about them. It’s the last working-class article of clothing that pretty much everyone in America wears.
Literally everyone. Presidents wear them on holiday to appear down-to-earth. CEOs wear them to shield their faces from surveillance cameras.
Kids wear them backwards to fuck shit up. It’s one of the last few clothing items that hasn’t been dichotomized by politics … unless you count certain red caps. Let’s not go there.
Needless to say, I’ve been through a lot of caps in my life. Like every other proud American, it started innocently enough: Dad took me to a Cubs game when I was seven or eight years old. (It was around this time I developed the lifelong sports hatred that lands me perpetually on the Sports Hateball podcast.) This was way back when Wrigley Field still felt like a quaint neighbourhood ballpark and not a tourist cesspool. We sat through them squandering a SIX-RUN LEAD, and on the walk home he bought me this huge wool cap that perpetually fell down over my eyes.
I wore the shit out of that cap. I didn’t give a shit about the Cubs – I cared about that cap. When I hit adolescence, shit got real.
Yankees cap (NO FAMILY CONNECTION TO NEW YORK HERE! ), Expos cap (THE TEAM NO LONGER EXISTS. ), Lakers cap (I DO NOT WATCH BASKETBALL.). I even got into that stupid Von Dutch phase (pls don’t @ me). My mother dubbed it my “identity crisis collection,” and for once she couldn’t have been more spot on.
How did I feel today? Well let me grab my Gary V caps and find out. I was participating in a historical pastime.
Caps had been around since wha – 1890, but they didn’t really become caps until the 1940s. I started wearing caps hardcore in the ’90s when every basketball player and their mum were rocking capricia vanderpump jerseys. Spike Lee wore a red Yankees cap and broke the internet, as they say.
Baseball caps became less utilitarian and more about self-expression. About style. About liking the same things as your friends, or wanting to.
I think I’ve spent enough money on caps in my lifetime to buy a small car. K thanks for helpin support me out girlfriend who balances our bills now. But during my decades-long fashionable journey, I’ve come to learn what makes a good cap and what doesn’t.
Crown shape: Slightly domed is where it’s at. Not too tall, not too flattish. Brim: Curved, but not folded in half like some college baseball team that takes themselves too seriously.
Snapback? Bo ***** kicker adjustable? Personal preference, but I’ll argue about it.
Material: Please do yourself a favour and stay away from the cotton polyester mesh-backed trucker caps that petrol stations and grocery stores love to sell. Unless you’re trucking an eighteen wheeler and it’s the year 1982: cotton twill is where it’s at. Traditionalists hate on me, but wool is hot and itchy.
As for pre-weathered/distressed caps, stop throwing your money away. Caps are meant to be broken in. Wear them outside, lean on roofs, wash them if you have to.
Learn how to sweat in that bad boy. This past year, I got to tour one of the last remaining American factories that still makes caps for MLB teams. Up in upstate New York.
Ancient machinery. Veteran workers who’ve been there 30-plus years. It’s called architecture.
Six panels form the dome. Perfectly calculated brim to frame your face. Sweatband keeps your masterpiece strapped to your melon.
It sounds basic, but there’s so much science that goes into getting those details just right. “They reinforced the stitching around those ventilation eyelets you see,” Mark, one of the workers, said as he inspected a cheap NO Name Brand cap they keep in house as a schooling tool. “That’s where most cheap caps fail first.” Damn right they do. Which is why my Yankees cap is going on fifteen years and others I’ve had only last a few months through sad wash cycles. Caps have also become cultural barometers.
You know someone’s asshole college kid when they rock that new obnoxious toddler-level bright camocap. Sad old man when they wear that dad baseball hat you hate but can’t quite put your finger on why. White hat, black hat.
Flip it upside down and it’s anarchist. Red, White, Blue, MAGA: politics. Patagonia brand faded to the perfect colour?
Hipstery artisan that cries to Instagram stories. Flat brimmed Yankees cap slightly turned just so? Brooklyn ass motherf***er.
We judge people instantly by the type of cap they wear. Entire generations can be classified by one travis head. International travel really brings this concept home for me.
There’s nothing more “I’m an American tourist” than a baseball cap. Get off the plane in Tokyo and some shop owner will look you square in the eye and know you’re American before you even open your mouth to speak. Note to all of you reading this from across the world: Mets cap.
Wore it as a sign of good faith during one of their promising seasons that eventually got sh*t all over by alligators. Patagonia medium wash fit snuggly on my head like a molded form. Walked into a cafe in Paris wearing my dad’s winter cap with a blazer and got THE LOOK.
Thousands of years of French resentment condensed into one man’s facial expression. But I was in this tiny-ass Italian village and some nonengrish-speaking old man spotted my Yankees cap on and instantly gave me the thumbs up and yelled “DiMaggio!.” Point is, caps talk. So how do you wear a baseball cap these days sans homelessness?
Mix it up with your outfit. Cap, navy blazer, oxford shirt, chinos. Cap is the new kickball sweatshirt.
It’s high-low but doesn’t feel like you forgot your mum told you to take your hat off inside. Speaking of which, who the hell cares if you wear your hat inside nowadays? Churches?
Fine dining establishments? Sure. Your boss’s basement?
Throw on a goddamn hat if you want coverage for that hair grease stain. Casual settings? Piece of cake.
Caps match anything. T-shirt? Throw on a cap.
Raincoat? Throw on a cap. During autumn, I love throwing on a simple grey cap under my camel hair overcoat.
Tailoring meets streetwear. Can’t lose. Won’t work?
Formal attire. Suit and cap? Nope.
Forever sucked aspiduthat jT tried to make it cool in the mid-aughts. Some trends should never catch on. Do I love when brands have started tapping into the cap market?
You bet your bald ass I do. There’s literally a cap for every price point nowadays. Five dollars at the petrol station all the way up to Travis Scott sh*t that’s being sold for more than my monthly subway pass.
Snyder does a great job collaborating with heritage companies like Ebbets Field Flannels to create that perfect capsule of updated fits with old school staples. Brands like ‘47 and American Needle provide great alternatives should you not have the funds to drop three figures on a cap. And if you’re really feeling it, you can buy the exact cap your favourite MLB player wears at the damn games.
Lat judged you for buying a New Era MLB brand cap until I learned how insanely difficult it is to break those fuckers in. Those wool caps are manufactured to be stiff as hell and will fight you every step of the way when washing them. It’ll be worth it, I promise.
Wear it as often as possible and let those creases create naturally. But please, please, please just wear a cap that means something to you. From your hometown?
Visited a city that got you hooked? Brand you admire? Doesn’t matter.
Just wear it and wear it until it becomes yours. Stained. Molded to the top of your cranium.
Bell-haired. Whatever. You know you wear a hat that you just throw on and no matter what situation you’re in, it matches.
The second people see that cap, they know who you are. Mine will always be that Yankees cap. It’s been through so much with me.
Chicago, New York, back to Chicago, Los Angeles, back to New York. Job transitions. Break ups.
New careers.

Girlfriends. The dog….man I hate that dog.
In a world of Instagramming your food and meticulously crafting your online personality, I love that no matter how ridiculous my wardrobe gets, I could literally be wearing medallions and lifts and still be caught dead wearing that Yankees cap. Years of sun bleaching cannot be replicated. A stained sweatband that’s perfectly molded to your head after years of wear?
Priceless. Hologram sticker covering the team logo has long since disappeared. But that blue has faded to a colour that doesn’t even exist in the Crayola colour catalogue.
To each of us it means something different, but I love that no matter how far I move or what I change in my life, that one thing will always be there. Here’s to the greatest American pastime accessory. Thank you caps.
Don’t let anyone ever say they’re for chicks. *****Do not ask to borrow my Yankees cap. ***



