live where there are a lot of small women?
Although my weight has crept up over the years (arrggg) it wasn't until I moved to New Orleans that I found a nice selection of petite clothes. I'm 5'3" and currently weigh ~160lbs, so depending on what I buy I wear a 10 or 12, and M to XL. In N.O. there were a lot of petit women - that old european blood line. So I left here, and thanks to a large asian community, there's a lot of short women - so the department stores stock a pretty good selection of petites.
But I haven't tried to buy cycling gear.