My go to when the weather is cooler, besides jeans and a big sweater, because that should be errbody's (spelling correct) go to, is a dress that fits like a potato sack and some kind of boots, with tights for warmth. This type of dress may not be that flattering, and it definitely doesn't show my curves. Wait, what curves? That's beside the point, the point is, it's comfortable and I love it. I think I've said this before, but as long as it's not an actual potato sack and it's somewhat in style, wear it girl! I will always buy a piece of clothing if I a) I love the style b) it's comfortable c) I feel confident and myself in it. This dress does it all for me.
Dress: Free People, Similar Free People
Boots: F21, Similar