Supreme Polar Fleece Pullover, $136
Ditch the old Patagonia and opt for this one from Supreme. Keep things street with a quilted nylon jacket or a bomber over it and work pants or straight denim. Alternately, you could class it up by throwing a tailored sportcoat on it. Yes, you read that correctly. Think outside the box a bit and wear it as a layer underneath a tan corduroy sportcoat — with leather elbow patches. Keep it gentlemanly all the way through with a pair of slim wool trousers in a light gray and clean sneakers like Common Projects.