First impressions count for a lot. If I saw someone wearing a shirt with a Playboy bunny on it I would not even give him a second glance. If he approached me and was cute and nice and stuff I might give him a chance but really I wouldn't recommend buying a shirt with a Playboy logo. For me it gives off an automatic image of being a player and not respecting women. I wouldn't completely rule someone out but I wouldn't like it.
I would think he is slutty. I wouldn't completely rule him out though because I admit I have owned a few Playboy things and I'm not slutty, but it's just the image that it portrays. I would have that in the back of my head but it wouldn't make me hate him
In my opinion, it gives a very bad first impression. We can't help but think that one would wear something like that only when he has some association with it, somehow, right? :) Afterall, clothes do reflect one's personality. So yeah, wear stuff that tell us what you are.
I think it would look fine. I hope so at least. I permanently put playboy bunnies on each arm , so in effect I'm going to be wearing a playboy shirt for life. I wish the girls would not hate on it so much, it makes it difficult for me because they are always jumping to conclusions about me being a player.