Hey, I get to post in the newbie achievement thread! I just rode to the store in street clothes. I had on a dress and boots. I always ride in cycling clothes and shoes. This might be a life changing ride, where cycling becomes more spontaneous, and less planned. I felt very chic, I must say. 
The funny thing is, I still turned my ankle to unclip even though I wasn't clipped in. You'll see, once you get used to clipless pedals, riding without them feels really weird, especially on those tiny little SPDs. I've had this idea that I would forget how to ride without clipping in, but it was all good. Yay!
'02 Eddy Merckx Fuga, Selle An Atomica
'85 Eddy Merckx Professional, Selle An Atomica
'10 Soma Double Cross DC, Selle An Atomica
Slacker on wheels.