I have dresses from ezibuy that I've worn through all seasons, winter with a pair of leggings and boots with a long sleeve top underneath and summer with a cardi or jacket depending on if I'm front of house or not. They've worn well.

I always have a cardi or jacket with me in office as like pp said the office never matches outside (especially since my coworker is menopausal).

I always seem to wear through shoes quickly though. I must not lift my feet when I walk or something. Boo.

Oh and I always buy last seasons clothes on sale just like the kids really lol. I'm not trendy lol.