A New Essay Over at GQ
Plus a mini-Walk-It-Off with milliner and fashion icon extraordinaire, Maxwell Newman.
Team!
A quick note to say that I published an essay over at GQ. It's about scouring London to find the perfect flat cap, but really it’s about grappling with personal style while trying to mature.
Here's a short excerpt:
“I dressed like a skater throughout my teen years and into my 20s. When I worked at a motorcycle metal bar in San Francisco, my outfits remained the same, only blacker. Eventually, I took to wearing a flipped-brim baseball hat—West Coast punk style—which was a questionable fashion choice (especially for someone who grew up in New England) at 24, let alone at 28, or 31 when I moved back East and continued dressing like a Tony Hawk’s Pro Skater NPC well into my mid-30s.”
Click here to read the entire piece.
In the GQ essay, I’m assisted by a man named Maxwell Newman, who works at Lock & Co. Hatters at 6 St. James's Street in London.
I asked Maxwell a few questions that didn’t make it into the piece, so I figured I’d share our conversation with y’all here. A mini-Walk-It-Off, if you will. Picture us meandering around an extremely stylish hat shop.
Isaac: How did you get into hat selling?
Maxwell: I was very lucky to get into Lock’s. I used to sell vintage menswear in Camden Market, which is where I developed a love for heritage style—hats included. I was already a bit of a hat-wearer myself and had become friends with one of the milliners at Lock & Co. I mentioned I was interested; she helped me get an interview, and the rest is history. It felt like a natural progression, moving from vintage to one of the oldest hatters in the world."
I: What do you look for when matching a hat to a customer?
M: I look for a few key things: face shape, sense of style, and what they’re hoping to express. A great hat should complement their aesthetic and enhance their look. It’s about balance—the hat should never overwhelm. It should feel like it belongs, as if they walked in already wearing it.
I: Are flat caps having a moment right now? Or would you say they aren’t currently in fashion?
M: Flat caps are definitely having a resurgence. They’ve never really gone out of style, but there’s a renewed appreciation for their versatility. They bridge the gap between casual and smart-casual. With the rise of vintage and heritage fashion, we’re seeing them styled in fresh ways—with suits, separates, or everyday wear. It’s a style enjoying its moment again.
I: What about hats in general? How would you say the hat market for men is doing at the moment?
M: The men’s hat market is thriving. There’s been a shift towards personal expression, and hats offer a subtle but strong way to show individual style. From trilby’s to beanies to bowler hats, men are choosing pieces that reflect their mood and personality. The renewed interest in craftsmanship and sustainable, slow fashion has given hats—and heritage brands—a real boost.
Large, heartfelt thanks to Maxwell—seen below—for all of his assistance.
In other news, I appeared on The Today Show recently recommending books—alongside Jasmine Guillory—to fabulous host Craig Melvin.
Click here to watch the segment—and here’s a photo of me on set thanks to Nathan Congleton (a fantastic photographer):
You can click here to see more of Nate’s photos from my Today Show visit—and feel free to keep up with my more frequent adventures by following me on Instagram.
Lastly, we’ve got some exciting walks coming up with V. E. Schwab(!!!) and Debbie Millman(!!!). I’m working on edits now, and should have ‘em to y’all soon(ish).
In the meantime, keep walking. ❤️
Looking for another way to support me? Consider picking up a paperback copy of Dirtbag, Massachusetts for yourself or a pal. Thank you!
Isaac, Linda Summersea here. Sorry to intrude. I sent you a message on X, so I'm not revealing content here. Cheers! (P.S. Hats! Gotta wear cool hats!)