My style is skewing classic these days, and the black loafers below in Finds came to live in my closet last month.

notasf, I do like patent leather, and good point about keeping rain in mind. Hah - good one about wearing trench coats to CA in winter

Bijou - I like those shoes, although the ankle socks would would not be my thing

runcarla - those are great, Clark continues to be one of my go-tos. They are great for classic styles and comfort

Lug or otherwise thick soles provide more insulation against cold ground so you might have a longer season with such shoes. Also, not all lug soles are the same. The soles on my zebra babies below are HARD in contrast to my burgundy oxfords (also below).

This may be just me, but although I like masculine style shoes like oxfords, black or brown leather reads too masculine for me. Thus, I go for patent, color, or colored patent. With the exception of one pair, I could say the same thing about my many pairs of clogs.

DonnaF what a great point about thicker lug soles being more insulated and working later into the colder seasons, and about the difference between flexible and non-flexible soles. And also great point about how color and finish can make a huge difference in styling.