In preparation of the move to wetter (and colder) climates, I think a nice pair of wet/cold-weather boots are in order. What’s nice about these Palladium boots is that they look pretty cool (and rugged) but aren’t overly puffy (like moon boots or overly slick (like wellies). The Pampa Thermal boots are waterproof through and through, with 3M Thinsulate for warmth and Dri-Lex lining for moisture wicking. The Pampa Tactical boot is not as spectacular for wet/cold-weather, but still looks pretty rugged, with Dri-Lex moisture wicking lining and 2520 denier Ballistic Nylon for high abrasion resistance. Both would be great with a pair of skinny jeans and a chunky sweater (and maybe a cute hat and warm gloves).