#2 - nWo
HONORABLE MENTION: nWo Wolfpac (although it's pretty much just the same shirt with red letters)
Was there anyone cooler than the nWo in the mid-90's? If you answered "yes," you're a liar.
Meet John Cena's dad HERE
Easily WCW's most popular article of clothing during its boom period, you couldn't pan to a crowd at any given wrestling show and NOT see someone wearing one. It's just a simple, graffiti-inspired design on a mono-colour shirt, but as we've learned thus far, less is definitely more.
Wearing this shirt made people feel like a hip outsider; a bada** that could "take over" any place they entered. And it still does - you still see tons of wrestling fans sporting these around.
Many tried to imitate the nWo in swagger and/or shirt design - D-Generation X, Bullet Club, even Randy Orton had an nWo-inspired shirt once...but no one did it quite as well as the originators.