I remember wearing IOU sweatshirts. They were the coolest thing in the universe for a time. You could get them 2 for 50 bucks at Merry-Go-Round. Plus, I would dress them up with a sweet color-coordinating turtleneck.
I also wore pj pants to class a lot in college. I admit it. Everyone else did, so it was ok.
For a short time in high school, I was the cheerleader with short, spikey purple hair. That was pretty cool.
During the Clueless-era, I rocked the plaid miniskirt with thighhighs. I guess those are still in style among the stripper set.
*Edited to add* The matching EVERYTHING outfits? Yeah, 5-7-9 was the place to go if you wanted to be accessorized from head to toe. I owed a few of those babies.