Throughout your life, you’ll have a lot of favorites. Then, like most things, your favorites will change.
As most young boys do, I defaulted to red as my favorite color. That changed to blue. Maybe now it would be brown. The whole idea feels a little sophomoric. I’ve moved on to more important favorites. Lightweight outerwear doesn’t rank itself.
Most of the pants, shirts, and shoes that were once my favorites, I look at now and wonder why the fuck I was so obsessed with them.
My longest-running favorite… is my hat.
Hats are hard. Harder than you think.
What looks good on me might not look good on you, and vice versa. Head shape, like most things, is not a universal truth. The wrong hat can make you look like a chud even if everything else is put together perfectly.
I was never able to rock a Supreme five-panel, something that shattered high school me.
Hats get played out—or just become corny—at an astonishing rate.
Outside of the classics—Yankees, Dodgers, and, for my sake, I’ll put the Mets in there; the black Mets fitted is on the Mount Rushmore—it sucks to see someone out in the same hat as you.
Your oddly niche pull from a brand you thought only you knew is suddenly sitting on the head of some guy in a trash fit.
If you see it on a “hats you should buy” list, just know it’s already too late.
And then there’s the other problem: most hats are just logo slop. Some company charging you for the privilege of walking around with its logo on prime real estate.
Let’s talk about my hat.
It’s an Outdoor Cap GL-555—or at least that’s its government name. It’s from Turkey and the Wolf, a sandwich shop in New Orleans.
Let’s get this out of the way: I’m not saying my hat from a Bib Gourmand sandwich shop is some super-niche, unbelievable pull.
But I am saying it is better than your best hat.
I bought this hat on August 5, 2023, on a trip to New Orleans—the same trip I proposed.
If you’re brave enough to brave the August heat in NOLA and get down on one knee, you deserve a little treat.
Turkey and the Wolf lives up to the hype. The food is merch-worthy.
As a sign of respect, I brought the hat back north as proof of a successful meal.
But also, I needed a hat.
I’d spent the whole trip wearing my Wythe hat, leaving the white to wilt in the New Orleans heat. I picked this navy one, figuring it would fit into the rotation better year-round.
I never really wore hats as an adult when I was still doing my hair every day. But as the need for daily styling—and the threat of scalp sunburn—became more of a reality than a bit, I transitioned.
After a rain-delayed flight back from New Orleans, I came home engaged and ready for the rest of my life.
But something of roughly the same tier was brewing in my wife’s giant pink luggage: my new hat.
This hat has developed from a high-crowned shield against a bad hair day into a Linus blanket. It’s the first thing packed in almost any situation.
It has more frequent flyer miles on it than anything else I own.
It’s gotten some walking-around money in its time. It made it to Magic City for my bachelor party—I’m pretty sure I’m the only person to ever wear Bode shorts and Birks there—then got its passport stamped across Europe on my honeymoon, always landing safely back at either JFK or Newark.
Never LGA.
It’s frayed, discolored, slightly stinky at times, but somehow no worse for wear. It feels like slipping your hand into your dad’s baseball glove—the one you wish you still had.
Then it disappeared.
I was last pictured in it on November 15, 2025—the day I went ring shopping with Frank.
After that came the stretch of the year when most things get lost: somewhere between Thanksgiving and the Kentucky Derby.
Somewhere during Arsenal’s 2026 race for the Premiership, their hat sat atop my table.
But when you’re traveling for an occasion like your best friend’s bachelor party, you need your best hat.
Panic set in on April 29. Somewhere between swapping my wife’s car and packing for Frank’s bachelor party, I realized the hat was actually gone.
I like to operate in a contained mess.
My mess.
Most of the time, I know where my shit is.
So I started retracing my steps. I left it here, so it’s gotta be there. No, the last time I saw it, I was in that car. Maybe I left it—
Nothing.
I was Gatsby staring at the green light.
How could something I loved so much not want me? Not come back to me? Did it not see how much I’d organized? How many other clothes I’d donated?
I deserved my hat back. I’m a good person.
Monday, May 18, was the day I officially gave up hope.
It had to be in my car. I knew when I cleaned it out to trade it in, it would be there waiting for me.
It was not.
At least the hope was gone.
It’s the hope that kills you, you know.
Arsenal beat Burnley 1–0 that day.
I love my Arsenal hat.
But goddamn, did I miss her.
Then, on September 24, inside a neglected dry-cleaning bag buried under my dad’s tattered dictionaries that I’ve driven around with since he passed, was my hat.
Sometimes hope doesn’t leave you floating in the pool.
My favorite hat.
-SP
Beautifully written FF