You know, for all the shit I got bullied about as a kid I don't ever remember it being about clothes. Also, unfortunately a lot of those kids had rich parents so they took their 900 sat scores and bought their way into Yale and Harvard and shit. They probably own a few Subways. I dunno, I don't keep up.
I don't pay much attention to what I wear. I stick to jeans and finally got a pair of boots that didn't wear out after a year. I have both colors of sweatshirts (black AND grey) and a bunch of t shirts from concerts and conventions my wife keeps trying to throw out just because it gets ONE hole under the sleeve or something. I can throw a hoodie over that and it's all good.
I did finally switch to boxers after I saw all the awesome kinds of commercials you can wear on your ass. Darth Vader's "Who's your daddy!" is great. I just now realized the force choke graphic is on the front. That's kind of awkward.
Anyway, if he's taking the time to dress well and feels good about it then that's awesome. Says a lot about his feeling good in his own skin. Even if that other kid is like my son and super anxious about making sure everyone is doing it right and it's not out of malice it's not like he's going to get a swirlie in the girls room because he tucks his shirt in.
FWIW she has got me more shirts than I have got myself lately so I can't really complain about the shirt situation.
I don't think guys care what someone is wearing most of the time so long as it's clothes, until you get into that bracket of money where the dress your date is wearing costs more than your monthly mortgage payment, if you weren't wealthy enough to buy your 17 bedroom mansion in cash. There are weddings, funerals, really nice restaurants, office dress codes, but.. eh. Whatever.