A brown houndstooth overcoat and a charcoal wool suit are absolute mainstays if you're crafting a classic wardrobe that matches up to the highest menswear standards. A great pair of brown leather tassel loafers ties this ensemble together. With an ensemble like this in your winter arsenal, you'll manage to stay toasty and look stylish despite the below-freezing temperatures. This outfit is the perfect answer to the question of how to dress your age well into your 30s.