Fashion Bleeds
No, that's not Beetlejuice shaking hands with NBA Commissar David Stern, that's current Memphis Grizzly Bonzi Wells when he got drafted by the Pistons in 1998. For this and more be sure to check out the amazing retrospective of past draft fashion over at nba.com. I've been to the draft twice, and they always show a video montage similar to the one I linked to, and Karl Malone ALWAYS gets the biggest laughs.
Second place has to be Jalen Rose's red pinstripe, I-just-ripped-this-off-the-back-seat-of-an-El-Dorado getup. I was in Indy for the draft when it was held there, and when Rose came out from behind the curtain, from a distance he looked like a walking corpuscle.