I ride about 3,000 miles/year and while I don't go out specifically dressed, I do find that I have adapted a few traditionally female elements into my bike 'kit'.
First, a sports bra (in almost all weather now). It gives me an extra layer in the colder months, and in the Summer relieves the 'nipple chafing' problem I sometimes get with the synthetic fabric shirts.
Secondy, tights. I ride down to 0F (and sometimes even lower!). In those temperatures, a pair of opaque tights under the regular biking tights makes a world of difference. I've even gone out a few times with just bike shorts over opaque tights, since they tend to look like bike tights from a distance anyway.
I've tried biking around (no further than my yard/driveway) in a sundress just to see how it feels. I LOVE the feeling and wish I could dress that way when riding through town!