I don't have a legitimate separation of warm weather/cold weather clothes is my wardrobe. That's something I can't come to terms with. I've worn this Free People dress a lot (I mean a lot) this summer, and to transition it into fall I'll just throw a sweater on it and add my boots, and it creates a nice I don't actually know what I'm doing but I think slob chic works look. It's finally cooling down here, but not so much that I'd need anything more than this. The sweater might still be too much, but I've conditioned myself to wear sweaters in 90+, so I'll survive. I'd also recommend a leather jacket or some kind of long, light coat with a pair of loafers.
Also, what do you think about this background? I like it quite a bit, though framing and lighting is still a small issue. I thought I'd spruce it up, and this looks a ton better than my bedroom.