Attempts to get him to wear shirts without writing on them–nice, simple, collared shirts from the Gap, for example–are all for naught. They remain neatly folded in his top drawer. Nice, khaki pants remain untouched for weeks, then months, until, one morning after the usual struggle, he pulls them out and triumphantly announces, “Dad, they don’t fit anymore. They’re too tight!” (Time is on his side.)

The struggle, I realize, is an ancient one, and I am surprised to find myself cast in the role of a doughty Ward Cleaver to the rebellious young Beaver. It’s odd, as I’ve never been held up as a paragon of fashion myself. As a child I tended toward the conservative, and I remember a couple of titanic struggles with my parents over a pair of pants that seemed to me a half inch too short. And I was heartbroken to discover that the blue camping shorts and plaid shirt that I begged my mother to order out of a catalog did not turn me into the cherubic blond boy in the photograph. In college I grew my hair long and took on a look that now I recognize as a precursor to grunge–baggy polyester work pants and ill-fitting coats that I bought at the old-men’s store.

My wife does not fully share my anxieties about our son’s clothes. It was she who caved in and bought him the Iverson sneakers ($69.99) and, in a moment of weakness and flagging judgment, succumbed to the camouflage hat. She is less bothered by the sight of him playing basketball with his hat on sideways, one pants leg halfway up his shin, Iversons barely attached to his feet. But she was on the front lines of a struggle the other day at the mall, where the only coats for sale featured, in large, bold letters, the name of their manufacturer: Adidas, Nike or Hilfiger.

Am I actually a cultural conservative dressed in liberal tweed, out of step with the times, nervous that my son is affecting the style of a hip-hop culture that makes me nervous? Is there a racial aspect to my ambivalence? Am I overly sensitive to the remarks of the playground moms who, as we watch our children play basketball, observe, “He’s really changed!” followed by meaningful silence? Am I fearful of his going the way of the shy, smiling boys I knew when they were children, and have watched slowly turn into cigarette-smoking teenagers who glower at me? When I say hello, sometimes, they look up, surprised, and the shy smile of their childhood briefly returns.

But what I once took as a largely urban phenomenon clearly is not: we went out to the small town where I grew up, the other day, an hour from the city, and as we played in the yard three or four boys strolled by, their enormous pants billowing like sails in the warm spring wind. I don’t want to be an old stick-in-the-mud, but I draw the line at pants trying to slide down the backside. “Dad,” he protests, “I have no belt!” Nor do I want my good-looking son turned into an unpaid walking billboard for Nike, or Adidas or Hilfiger. Beyond that, I’ve probably got some work to do myself, updating my own antiquated and overly mythologized sense of fashion and cultural iconography.

The baseball hat, after all, is as American as apple pie, emblematic of virility and a peculiar brand of American male self-satisfaction. The fact that he likes to wear his sideways shouldn’t send shivers of dread and alarm down my spine, should it? I was driven from the sport myself in the late 1960s by an overzealous coach who thought he was going to save America from communists by making me get my hair cut. When I did, finally, he said “shorter,” and I quit instead.

Baseball catchers wear their hats backward, and football players in postgame interviews, and half the male college students in America, drifting around in their smug little packs, looking for a woman or a beer. But sideways? What does it mean? Why does it bother me?

“Dad!” my son asks during one of our morning skirmishes, rejected garments strewn around the floor, his hands raised and shoulders shrugged in an eternal gesture of astonishment and dismay. “What’s your problem?”