Holy shit. I went through so many embarrassing phases it's....well, embarrassing.
High School: Grunge look. I can't believe my parents let me leave the house. And looking back at pictures of myself it's no wonder I didn't get alot of action from the ladies.
Early College: Metro-sexual look. I started dating a chick who wanted me to be preppy. I got a part time job at the Banana Republic and BLAM! I have to admit, I was looking pretty good. But God, I'm surprised my friends didn't kick my ass.
Late College: Stopped dating that girl and thus dropped the metrosexual look. I then entered the most embarrassing phase of all. I started getting into the hardcore/punk seen. So I adopted that look. Died black hair, gauged ears, and the worst part - I was "straight edge". A couple of my good friends were good enough to tell me I was being an idiot.
Now: I think I'm finally out of the fad thing, as far as appearance is concerned. I throw on whatever and just try to look halfway presentable. I'm finally old enough to not care about fitting in to cliques or looking cool.