42. Joe Boxer
Because sagging your jeans was a trend in the '90s, your drawers game had to be on point. Luckily, Joe Boxer was around in the '90s to show off some personality and humor when you were very nearly showing off the goods. Boring old solid colors were no longer acceptable. If A$AP Rocky was rapping in the '90s, he'd have told us he was Joe Boxers down to his boxers, and we'd be right there with him.