I ride on both sides of the cultural divide, depending on the trip. There's a grocery store a mile from home, so no need to get all kitted up for that trip. BTW, if you want to be retro-cool (or totally nerdy in the most geeky possible way, depending on your view), here is some gear that you can wear on or off the bike. I've never bought any myself. Check out the seersucker shirts!:
http://www.rivendellbicycles.com/webalog/clothing/