#8 - D-Generation X
The Kliq ran professional wrestling in the late 90's.
While Scott Hall and Kevin Nash were taking over WCW, Triple H, Shawn Michaels, and X-Pac were taking over the WWF. The Kliq's respective stables bore striking resemblance to one another - they were both controversial, anti-establishment, and unapologetically obscene wrestlers that wore black shirts with their logo on it.
A former WWE writer just went after JBL for his comments HERE
Which makes me think...if they were so anti-establishment, why did they allow the company to sell their merchandise? I don't know, maybe I'm overthinking things.
Anyway, while not the most popular shirt at the time, it was still immensely popular amongst WWF fans who wanted to be cool like DX. The shirt also featured their signature "suck it" on the back, which did admittedly make it a little harder to wear in public than other wrestling shirts. Still, it is easily the best DX shirt they've ever put out.
Well, except for the "Vince Likes Rooster" shirt. That may be the greatest of all time.