There is nothing more comfortable then a thick, oversize sweater and the skinniest-of-skinny bottoms. J. Crew and LL Bean are great for men's sweaters (my personal favorite). Wear classic jewelry (break out your pearls and Yurman, ladies) and super skinny jeans (so you don't get too used to only wearing big clothing - avoid winter weight gain!), and you're all set!
Have a great day!