Levis 501 Blue Jeans
When I was in junior high, Levis 501 shrink-to-fit blue jeans were the coolest thing to wear. I remember skimping on all my other clothes just so I would have enough money to buy a few pairs of 501s.
These commercials are what were playing on MTV all the time:
This one has Stanley Tucci:
This one shows how we used to wear them: a little rolled up with white socks and penny loafers. I think we were all trying to look like Back to the Future.
In the end, Levis 501 NEVER fit me well. They always had a horrible loose bit at the back that would poke out and show the world my undies, no matter how tightly I cinched them with a belt. They might have been shrink-to-fit, but they never fit me.