I look for good fit (so the damn skirt stays in place), a sensible fabric, and a nice active cut. If I need a slit to walk, it's cut too narrow. If it needs a crinoline to hang right, it's too full. Most skirts are too narrow to bike in easily - they're fine if you have a step through frame and are not going far. If you have a diamond frame or are going more than 3-4 miles, you'll really want something you can move in.
Kilt style wrap skirts seem like they'd work best. Good freedom of movement, and they only need to fit properly at the waist. Fixing fit issues is also pretty easy, even if you can't sew very well. I've been having a hard time finding 'em tho![]()
I commuted in a skirt this morning!! It's an older bell-shaped skirt. My commuter is a step thru.
'Twas a bit chilly.![]()
I haven't read the whole thread, but I thought I would chime in.
My cycling consists of 90% commuting and I ride in my street clothes. In fact, i actually do not own any cycling shorts (hate the padding, make me feel like I'm wearing a diaper).
Having said that, my current saddle is a Brooks B-17 women's. I've only had it for about a month now, and I will admit that the first 3 weeks involved some sit bone pain and a fair amount of adjusting. I think I've finally found a happy setting and the saddle's getting more comfortable.
In the winter I'll don waterproof jacket and pants and in the summer I usually just ride in my capris and flip flops.