My eldest child, 17-year-old H. favors a sartorial style heavy on hemp necklaces (which he creates), tie-dye shirts and flip flops. I'd love to see him in snappier attire - because he's so handsome - but I assume he'll eventually retire the tie-dye, just as the rest of us did.

Since I know that the faux-hippie garb is just a phase, I mostly leave the issue of how H. dresses alone. It's his business, and even if I wanted to, changing how a teenager clothes himself would be an exercise in parental futility. I know this. I get this.
But there are two pieces of H's dresscode about which I seem unable to keep my mouth shut. You see, he has this hat that is completely NOT in keeping with the rest of his relatively acceptable yuppie Deadhead look. I like to call it his Kevin Federline hat. I don't know where he got it, but it's awful. It's a trucker cap of garish kelly green and white, with a perfectly flat bill. It's very thuggy looking, especially since he only wears it backwards. And he wears it often.
When I see my son in this hat, I feel the hairs on the back of my neck start to prickle, as I fight the urge to comment yet again on how much I hate that damn hat. I've explained to him that it ruins his otherwise put-together look. I've told him that girls must hate it. I've offered to buy him a new hat to replace it.
None of it has worked. He continues to wear the Godawful KF thug hat on a nearly daily basis. And now that he knows how much I hate it, I suspect that he sometimes wears it just to get to me, when I've irritated him in some way. And it does get to me.
I've considered disappearing the hat - just making it go away and then lying about my involvement in its absence, but I know that would be Wrong. Right? Plus, he would know it was my doing, no matter how much I protested my innocence.
The other issue is that of his exposed boxers. H. is a very lean boy, with no hips to speak of, and his pants have a way of riding down to about two inches below his boxer waistband, exposing his underwear. And really, I don't want to see his underwear.
This is not the same look as those baggy-pants kids who purposely let their pants ride waaaaay down low, prompting some lawmakers to take notice.. This is more subtle, with just the merest hint of undies peeking above his belt. But it's too much. And it drives me nuts. I find myself constantly telling him to pull his pants up, which he never does. It's literally the last thing I say to him when he gets out of the car each morning at his high school. I don't say, "Have a good day!" or "Study hard!" Instead I find myself barking, "Pull your pants up, son," in the sternest voice I can muster, as he ambles off to class, backpack slung over his skinny adolescent shoulder. The last glimpse I get of him each morning is a flash of boxer waistband, turning the corner into the school building. This does not make me a happy mama.
I realize that these are battles I cannot win. And I am violating one of my own parenting mantras (choose your battles) by engaging with him on these two issues. But I can't seem to let them go.
I am sure that my mother would tell you that this is just payback for the horrifying haircolors, Flock of Seagulls bangs, and really short denim miniskirts that I favored circa 1984...
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