Well, since the boatshoes, chucks, purcell's, etc already got mentioned.. how about Toms? I saw guys wearing them quite a bit last Summer. After being broken in, they look pretty cool with slim pants or jeans.
opening ceremony is supposed to release their version of the bass weejun. an excellent loafer. i'm pretty sure it's over the $100 mark though. if you do like the bass weejun try getting a pair on ebay. that's where i kopped mine and it was well under $100.