At this point, I'm assuming that anyone who is saying that James O'Keefe looked like a realistic pimp hasn't actually watched the video carefully enough to see O'Keefe's outfit.
Luckily, he wore said outfit for a Fox and Friends interview. Here it is, though he wore big sunglasses and a hat in some of the videos and he's omitted them here, and I'm pretty sure he was wearing a wifebeater rather than a suit in at least one video*:
If you can look at the fake fur jacket alone and think anything but "Attendee at a Frat House Pimp and Ho party," then I am forced to believe you've never seen an actual tough guy.
*Hint to all potential fake pimps, that's a step in the right direction.