Decided to try the "cycle chic" thing today, just to see what it was like. I think the last time I wore a skirt or dress on a bike was when I was 12 and my mother wouldn't let me wear pants more than one day a week. So, I pulled a pair of lycra tights on over the pantyhose just to make sure I didn't flash anyone inadvertently and set off down the road in my denim skirt and medium heeled dress shoes. It was doable, but the skirt tended to bunch up and get in the way. Plus, the tights were needed. Either that or shorter cranks to keep my knees from flipping the skirt up so much at the top of the pedal stroke. Because the top tube slopes so much, I only had to pull up to a curb to get my leg over it to dismount at the end.
Coming home, another cyclist pulled ahead of me at a red light. This normally annoys me, because they're assuming they're going to be faster without knowing anything about me, but I suppose the sight of the purple heels and skirt could have justified this assumption. Felt good to pass this person, who really wasn't very fast at all. The skirt slowed me down only very slightly.
Would I ride in a skirt again? Probably not. It wasn't all that comfortable and it doesn't take much time to pull one out of a pannier and put it on at work. Still, good to know I could pedal off somewhere close by at lunch time without a complete change of clothing.