One quiet afternoon a few weeks ago, I was jogging along the water in Bay Ridge when I spotted someone in front of me calmly clicking down the path in a belted overcoat and brown wingtip shoes.
Conjure in your mind “a man commuting home in New York City in 1990 … or 1970 … or 1920,” and it was him, but a live 2026 version.
The Ghost of Footwear Past, but with AirPods. I had two thoughts: This guy looks great, like how I’d always imagined I would dress as a working adult. And his feet must be killing him.
But when I pulled up next to him, there was no grimace in sight. I stopped him to compliment his shoes and ask if his toes were crushed, and learned that his name is Jaques Anthony Bettig, he’s a 26-year-old lawyer, and the answer was no.
Breaking them in “was really painful,” he admitted, but now he was sailing.
Jaques Anthony Bettig
“I try to walk 10,000 steps a day,” he said, showing me an app on his phone to prove it. “I walked 19,000 steps on Monday, and I don’t have blisters or anything like that. It’s manageable.”
As Bettig shuffled off towards the Verrazzano Bridge, I was inspired. If he could be that athletic in a pair of hard leather shoes, I should at least try.
“Who cares?!” the crowd jeers. “Just go to work looking like a camp counselor, it’s fine.”
That’s fair. But when I moved to New York City 15 years ago, I had an inspired vision of what my life would look like. And in that vision, I’m wearing loafers.
As I saw it, good hard-soled dress shoes were an essential part of the New York uniform because they’re serious, and this is a serious town. When I was a kid living in San Diego, California, I had a Sunday school teacher who wore flip-flops — and we were Presbyterian. I wanted something a little more dignified for my future.
A proper dress shoe, in my mind, is timeless, even modest.
They’re less “look at me” and more, “I’m but one humble cog in the 400-year-old project called New York City.” People wore these things to watch baseball games and to fight the British. My great-grandpa danced in Lindy Hop competitions in Queens in the 1920s, and he didn’t have high-performance sneakers.
But then another thought took over: Bettig belongs in those shoes, but do I? He’s an attorney. I write a daily newsletter that’s also a TikTok series, and I’ve spent 15 years thinking about this while failing to move on from Vans. Maybe dress shoes simply aren’t me.
I asked Ian Bradley, a stylist who’s worked on covers for T Magazine and campaigns for Thom Browne, whether it’s worth fighting to be a dress shoe guy or if, even in New York City, we’re headed towards a future of all sneakers, all the time.
His take: Now is the time to break in some leather.
“I think there’s a shift now where people want to be more formal,” he said, even if “athleisure is here to stay.”
He sympathized with my journey. He said he grew up a sneaker enthusiast and only came to the hard-soled life at 34, when he found a pair of second-hand Prada loafers that felt just right. But he cautioned against waiting to magically age into your dress shoe phase.
“I would see a 20-year-old [in Oxfords] and think, ‘he looks cool,’” he said of his early days in the city. “It’s a self-inflicted thing — ‘I’m not a fancy pants, I don’t feel comfortable in this shoe’ — that mentality, that’s the challenge.”
He said some New Yorkers are just natural dress shoe wearers — former Doc Marten teens, for example, tend to make the transition easily. For the rest of us, he had some practical advice: Get your shoes half a size too big, slip an insole in there, and “commit to the bit.”
For whatever my hang-ups have been about dress shoes, specifically, I’ve never been afraid of buying myself a present. So I went to a shop I like called Cueva, where the look is elegant for the heck of it, and tried on a deeply discounted pair of brown loafers.
As I was standing around, trying to become one with the leather, I asked the store’s owner, Justin Felizzari, if he thinks there’s a shift toward formality underway. He said his dress shoe sales are “easily double” what they were the previous year, but he said it’s more about people experimenting rather than customers trying to adopt a certain uniform.
“New York City is the best dressed place in the world,” he said, “and I’d like to think it’s a very judgement-free city, which ultimately creates this feeling of, ‘I’m going to wake up and put something together that in another city wouldn’t necessarily work.’ People try things.”
He said on Saturday mornings, for example, a lot of people come into his shop in Greenpoint wearing loafers with sweatpants.
As for my loafers, there was no happy ending. My heels kept slipping out, and to Felizzari’s credit, he didn’t advise trying to force it.
“There’s different types of leathers and different types of cuts, so sometimes a shoe might not work for you from the beginning and wearing it every day isn’t going to change that,” he said.
But I think I’ll try some lace-ups. And not because I should, or because it’ll make me a better New Yorker or more of a grown-up. (I’ll be 23 forever.) I’ll try them because I want to, and truly no else cares. Or, I’ll try them once this slush clears.
For now, I’m wearing Bean Boots.
