Lol, am I the only one who used to be a metalhead during his teen years?
Obscure band t-shirts tucked into black jeans, large wallet chains, black hoodies, even the occasional inverted pentagram as an accessory... those were the times. Oh, and not to mention the short period when I painted my nails black.
Looking like an All Saints mannequin about 3 years ago.
I've been through a range of different styles, but don't regret any of them really because they reflected what I was into and where I was at at the time. There have, however, been clothes that i have bought that clearly didn't suit/fit me very well, which were a mistake.
Slightly off-topic but it's been mentioned in this thread: I find dressing to go out to clubs/bars really difficult. If I know we're just going to a couple of smart bars then it's fairly easy, but if clubs are involved then I'm never sure what to wear. It's always roasting hot inside clubs so I end up sweating in anything more than a t-shirt or shirt; there's no way I could wear a cardigan, jacket or blazer. I also always worry that people will spill drink on me and so I don't ever want to wear anything too smart.
My biggest fashion regret is that 3 or 4 years ago I wore lots of Jack Wills, A&F, and Hollister, so I looked like a walking advertising board.
Merc - Cause it's winter, i tend to throw on a chambray shirt, quite light to wear but doesn't make walking from club to club a test to see how my body copes in the freezing cold. Another one i use is just a plain t-shirt and jacket, take off the jacket in the club and ta-da!
Evisu jeans! I owned 3 pairs of them back when they were a big deal, before became a hip-hop trend. It makes me cringe to think I had those ugly painted guls on the back pockets.