I agree with alot of what's been said here. I NEVER "dress up". As mentioned, if I wanted to wear shirts and ties, I'd work in the business world. I can't stand 'em! I do wear nice, crisp dark jeans and a button up shirt, usually of varied colors, (and maybe a jacket,) to interviews. I think clean crisp jeans are an almost perfect item to express a nice look while putting forth a vital image of physical competence. Usually similar outfits to rehearsals- sometimes slacks for a first rehearsal. Often Hawaiian shirts to rehearsals once I feel comfortable in the group. They're bright and fun and flashy and help to lighten the mood, I think. And I *have* to wear blacks often enough. I hate to volunteer to do so. My favorites are flannel shirts, preferably colorful. Sleeves always rolled up. Comfortable shoes, like Merrels or something. Sometimes steel toe boots to a busy Tech if I'm running the deck. Backstage blacks, (or at least dark clothes,) but if I'm calling the show, I usually just wear whatever I want as long as it's nice looking, (see reh garb above,) only giving slightly more consideration to darker colors.
As for the high school situation, as I recall (difficult as that may be!) stage managing in high school was a unique opportunity to learn how to assert authority and earn respect, and the kids tended to get into the heirarchy and roles that developed. So what i'm saying is that I think high school stage managers should take the time to dress a bit nicer, (but still hip! Blacks work nice for this,) in order to practice these lessons.