Although pretty much anything goes for business attire these days, I find myself much more comfortable and productive in a suit and tie. Today found me in a heather navy flannel suit, yellow oxford shirt, Navy/gold striped tie, and black captoe oxford shoes. Actually, I carried the shoes in my briefcase and wore some LL Bean boots through the slush. I can't afford to ruin good shoes by exposing them to salt and ice.
Throw on a charcoal overcoat, leather gloves, Irish guncheck cap, and plaid scarf and I'm ready to brave the elements. Actually, hardly braving much of anything as my car seats are heated and my only exposure is the one block walk from my usual parking spot to my office. Here are my tips:
Get a hat that you love. Whether it be a stocking cap, fedora, bowler, whatever. Get one that makes you feel good and wear it everyday.
Wear a charcoal overcoat. When you rub up against a grime covered car, you'll wish you had. I made the mistake of buying a camel colored overcoat a few years ago and rarely wear it because I'm afraid I'll soil it.
Get good boots. Wet feet make for a long day. I like the Bean boots made in Maine, but there are plenty of options out there.