Hmm, I think you are younger and shapelier than me
(not putting myself down but the little bulges would show)
I like the hoodie thing. That would look nice on the right person. Good colour.
I'd wear Dress 2 with tight jeans
I persoanlly don't like high wedges.
I have seen someone my age (40 ish) look amazing in Boots 1 but the rest of the outfit was quite understated