I imagine my father at Sperrys. He’s not a hard-core blue blood like some of his Main Line friends outside of Philly. But he certainly dressed the role at the time. Brooks Brothers to marry my mother. Stonewashed jeans and LLBean buff shirts to confuse the kids. And, of course, boat shoes. Practice. Sure. Modest. The first pair of “dad shoes” in my life.

I was appalled by them. Dads are not cool! So I got into sneakers: Vans, Chucks, Nikes. Then, in the mid-2010s in New York, a few of my best-dressed friends started wearing New Balance 990v4s. Even though these aren’t the dad shoes I grew up with, they were still dad shoes. Practice. Sure. Modest. And . . . cool? Maybe I was just following the trend, but I got my own pair and loved them. A few years later when I went to the hospital for my son’s arrival, they were up. For one thing, I couldn’t pass up the opportunity to wear dad shoes while becoming a dad (the very act of which, I realize, is a dad joke). But on the other hand, I expected to stay by the bed, run for the essentials, and do all the other things expectant dads do while their partner does the real work. I knew my 990 was up to the task.

New Balance Made in USA 990v5 Core

There’s a theory, often proven, that men freeze up when it comes to wardrobe when they have kids. My son just turned three and my closet looks considerably different now than it looked the day he came home from the hospital. But my 990s remain. Maybe it’s their comfort, or their infinitely malleable aesthetic. Maybe I was indeed frozen in place, just a little. Maybe the same thing happened to my dad – he found a choice shoe, then I came, then my sister, and, boomdad’s shoes.

For my son, the 990 will be the first dad shoes in his life. And if he’s like me, he’ll reject them. His loss. But maybe in 30 years he’ll find himself with a pair of 990v13s and think, Man, dad actually understood a thing or two. I mean, damn it, I love LL Bean chamois shirts and stonewashed jeans now.


Is it time to get a pair of boat shoes?

This article originally appeared in the SEPTEMBER 2022 issue of Esquire