Keen has awesome flat soled, leather and waterproof (they are really waterproof - I went sledding a couple years ago in Baby Bern Keen boots) boots that you could get some CA mileage out of, especially on your 50 some degree days. You could wear with skirts at home, nothing on your legs.
Look at the KJ's (I just got them and I love them)
http://www.zappos.com/keen-kj-boot-slate-black
Baby Bern
http://www.zappos.com/keen-bern-baby-bern-boot-purplie
or Shelby
http://www.zappos.com/keen-shelby-hi...ack-full-grain
Kindra
DS1 6/06
DS2 9/08
DS3 9/08