Tee-shirts with 'witty' sayings - I had one that said 'It's always better in the Hamptons'. Yeah, I still don't know what the hell inclined me to buy that tee, but I was 13 and it seemed so 'right' @ the moment.
Studded Belts - After I purchased the belt (from Hot Topic, no less
), I went 'stud crazy' and studded my converse, tee-shirts, the pocket-edges of every single pair of jeans I owned as well as my bookbag. My mom wasn't too pleased.
Band Tees - Blondie, New Order, Elvis Costello, Leonard Cohen, New York Dolls, The Smiths... I was quite obsessive. I think I will hold onto these forever. It's fun to pull them out every once in a while, even if only for a good laugh.
Patchwork Bell-Bottoms - It was the 90's... I was about 10-11... These jeans meant the world to me. In retrospect, as hideous was they were, I felt great every time I wore them.