I'm the Anti-Tracky, I'm a bit 1950's like that (pity I don't have the 50's house pride), I wear jeans (agree with K, I think stretch jeans are a comfy option), and then a comfy top. Tshirts with a warm cardi are a great way to go in winter, and shoes are a must (I know that's very flylady of me) but they keep you warm, and make you feel dressed and ready, unlike slippers, which are warm but make you feel a bit snuggly and can't be bothered-ish.

If the weather's warm, how about skirts? Some skirts can be really comfy (on the cooler days you could even wear leggings underneath), and a tshirt, cardigan and ballet flats would be pretty cute.