Rode in shorts once, for like a hundred feet (moved bike from the street to parking space in front of my house after they did some road work). Felt freaky as hell, but I wasn't about to gear up for 30 seconds on the bike. However, when I'm out riding, helmet, jacket, gloves, jeans (i know, i know) and over the ankle hiking boots, though researching regular riding boots. Saw a guy not too long ago around here riding in shorts and flip-flops...thought the guy was out of his mind. If I ride to the train station to go to work, i'm in slacks, but its a PITA to carry a second pair of shoes plus a pair of pants in my backpack.