These are the factors that determine what I wear for a ride:
1. Destination -- commuting gets works clothes, utility/fun rides, I dress for the weather
2. Distance -- more than 25 miles, I'll put the lycra on under a pair of baggies (or, if weather demands, tights)
3. Temperature -- lower temps, naturally, require more layers
Some of my wardrobe could be called cycling-specific (1
pr lycra shorts, 1 bib, 2 jerseys, 4
pr socks); other parts are simply moisture-wicking T's or shorts. Then, there are street clothes, which serve the purpose for a ride under the right conditions (see above).
I'm not sure what social message that sends... other than "I don't give a sh** about social factors." (Not angry, not hatin', just sayin')
Not trying to crap in your cornflakes, either, Steve, just my 2c.