Winter is the hardest season to dress professionally for me. It's cold, and I just want to wear jeans and a sweatshirt. I generally prefer dresses and skirts over dress pants throughout the year and that includes winter. My biggest challenge is shoes. Who wants to wear heels in the snow? Boots are tough to pull off with dress pants too. My go-to option is ankle boots with a dress or skirt.
I love this sweater/skirt combo! It looks nice and warm, but equally chic. I also really like the jumper and top underneath. I generally wear the 3rd option, which is a wool skirt with different top options, tights and boots.