When most men find out they are having a son, they look forward to the day they'll teach him to set the hook on a fish, grill a perfect steak, or box a trifecta at the track. I imagined doing all those things, but I also flash-forwarded to introducing Nicholas to my tailor.
During my own childhood, I spent summer vacations watching my maternal grandfather select his suit, tie, and chunky cufflinks before heading off to the morning train and his job in Manhattan's Garment District. As a teenager, I logged time in Paris with a doting aunt who ran the buying offices for Bergdorf Goodman and spoiled me with Charvet shirts. I know my fondness for clothes is a vice, but I blame genetics.
Teaching my son, Nicholas, who's now three, how to dress strikes me as part of raising a good guy — like drilling "please" and "thank you" into his head. It is an open question whether these lessons will have any lasting effect on him. Regardless, I know the process has changed me. What once was my library in our Manhattan apartment is now his room. My closet has become a lair where silk neckties are appropriated for pirate scarves and then left balled up on the floor. The costs of raising him have also put my own wardrobe into remission. Thanks to his school tuition, I no longer buy bespoke from the United Kingdom but off-the-rack from the Republic of Banana.
As I've been downscaling for myself, I've been upscaling for him — toddler-size moleskin trousers, Hackett tweeds, cashmere sweaters — an indulgence I did not experience until I started banking my own paychecks. And if I'm being totally honest, my competitive streak is partly to blame. My wife and I represent the diversity in his nursery school class: We both work. We are not blond, and we still fly commercial. But when Nicholas rolls into school, Daddy wants him looking like a million bucks — even if shortly after he arrives he's covered in finger paint or apple juice. In the early innings of his development, I seldom exercised my veto power even as my wife carted him off to Christmas parties in velvet knee breeches and footwear suitable for a courtier to the Duke of Urbino. Around the time he started walking, however, I began a series of interventions: Pro-Keds sneakers, khakis, a Patagonia fleece. His transformation from doll to dude had begun.
One of the things you realize pretty quickly upon entering the boys department is that most of what's available falls into two camps — faux athletic gear that presumes your son will be spending his days attending Tae Bo classes, or what I call Lil' Hipster — vintage concert T-shirts, fatigues, and everything you'd need for a 24-inch-tall Joe Strummer. I have sought out more traditional options like Crewcuts (J. Crew's excellent kids' line), Polo, and Best & Co. — companies that make boys' clothes that even a man might envy.
