What's the difference, fashion-wise, between riding in a "street" skirt vs. riding in a skort or over-skirt that's designed for cycling? I don't see the objection.

The last time I looked good in very short skirts I was 14 years old and anorexic. So besides cycling skorts, the only skirts/dresses I wear (ever, not just on the bike) are just below to just at the knee.

When I commuted, I always wore a dress. I had a diamond-frame bike, so it was loose and flowing skirts.

Nowadays I'll wear a dress or skirt to church or out to dinner on my step-through commuter - two miles max (each way) at a gentle pace.