A grey plaid overcoat and charcoal wool dress pants are absolute wardrobe heroes if you're picking out a classic closet that matches up to the highest menswear standards. Loosen things up and complement this ensemble with a pair of dark brown leather chelsea boots. In the winter months, when warmth is essential, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a striking illustration that you totally can stay comfortable and remain equally stylish in the winter months.