#1 Chyna/Eddie Guerrero: Va-Chyna
If The Rock's "Pie" shirt represented almost everything awful about the Attitude Era, then this represented absolutely everything awful about the Attitude Era.
Alright, let me give you a quick rundown - one of Eddie Guerrero's first storylines in WWE was that he was courting Chyna, an imposing female wrestler that was often jokingly mistaken for a man, both in kayfabe and by fans. Now keep in mind that, at this time, Eddie Guerrero was rightfully considered one of the finest professional wrestlers in the world and Chyna was one of the biggest draws in the women's division.
So this is the best they could do? A shirt that says "Va-Chyna" (heh, get it?!) on the front and "Enter at your own risk" on the back? Really?
To start, this shirt made no sense for the Eddie Guerrero character. He was supposed to be somewhat of a Latin Lothario who seduced the "mamacitas" with his "Latino Heat". Why, then, would HE insinuate that Chyna was transgender? I mean, come on...how is "Va-Chyna - enter at your own risk" NOT implying that? This would've made a little more sense had they made it for DX, but honestly, it would probably still be on this list even if it were a DX shirt.
Secondly...Va-Chyna? Are we being serious here? Of all the low-hanging fruit that the WWE picked for the shirts that made this list, this is by far the lowest. Hell, it's practically touching the ground. This was a wholly unnecessary sex pun that made for a wholly unnecessary shirt.
So let's put it all together - misogyny, sex jokes for the sake of sex jokes, crass humour, and transphobic/homophobic tendencies...yep, this is the worst shirt that the WWE has ever made. It may even be the worst THING that the WWE has ever made. How anyone thought it was a good idea to make this shirt and sell it is beyond me.