I love posts like this.
I'm with you on the fingerless gloves. They're my one necessary thing. I think there's something about a pair of fingerless gloves that says "I am serious about being on this bike" even if the rest of your clothing says, "I don't really care I am on a bike."
Whenever I have to go anywhere in town, I ride my bike 95% of the time. If it's not raining I wear the ordinary clothes I'd wear while walking down the street – so all my favourite skirts are the ones I can wear on a bike and not look overly indecent, though there has been a degree of trial and error in this. If it's raining: a merino top, cycle tights, and a waterproof jacket, and one of those fluoro bag covers. And a headband under my helmet to keep my ears warm. If I'm riding a really long distance, I pretend to a be a sporty person and gear up with those padded pants, and I take a change of clothes. There's something really good about knowing you can go as fast as you want and sweat as much as you want because you've got a nice fresh bundle of clothes to change into at the end.