I wear skorts for errand rides, shopping, going to appointments, bike path riding with friends. Once in awhile, I have worn one on short (less than 20 mile) road rides. I finally found one that doesn't fly up a lot, the Terry Coaster skort. I am not modest and don't really care about going into stores with my bike shorts on, but wearing a skort makes the ride feel different, less pressured, and I do like them if I am going out to eat; I feel "dressed up."
The chamois tends to be different and not so conducive to long rides.
Last edited by Crankin; 11-30-2011 at 04:15 AM.
2015 Trek Silque SSL
Specialized Oura
2011 Guru Praemio
Specialized Oura
2017 Specialized Ariel Sport