I haven't quite got my head around the change of season, although I've stopped buying anything too summery.
I think I need some more long boots, although I do have a pair somewhere in the loft with straps around, which taps into the "pirate boot" trend. I had the most gorgeous pair in the 80s - all slouchy soft leather, with straps and ties - I basically walked through the soles in the end. <sigh>
I wouldn't rule out a lightweight/blouson jacket - I do have one, but it's denim, so doesn't work with jeans (not a fan of double-denim).
I had a jumper splurge last winter, so all set there. Looking forward to digging those out again.