anything remotely breathable i prefer to wear without socks. anything with heavy leather like cp's i'll wear socks because i don't like the feel of wet leather but since i'm blessed with minimal sweat/odor i can get away with being sockless a lot.
Personally i only dont wear socks when im wearing boatshoes or toms but if you want to still wear socks but have the sockless looks i'd advise picking up some toms socks, i got mine at journeys a year ago when i bought my toms so i could wear them with my toms (which i rarely do) but they worked great in the sense of being a sock but being completely hidden.
I dont wear socks with vans or other canvas sneakers - my feet are always too hot wearing socks. And since canvas breathes easy they feel just right with no socks. As long as you don't wear them every single day, they dont smell.