I wear them quite a bit for various occasions. I wear them for work, for casual/school run/shopping etc in both summer and winter.
Winter is usually with boots and patterned tights or sometimes boots and socks (if long skirt and not too cold) but that all goes pear shaped when you visit somebody who has a shoes-off policy and I'm sat in their living room in a nice dark green skirt and black socks with pink heels and toes. Nice look. Try to think ahead on that one.... In summer skirts with flip flops.
Really missed the boat on buying ballet pumps this autumn and can't afford some now because I want to buy a pair of boots.