Reach for a black overcoat and a grey three piece suit and you'll be the epitome of classy men's fashion. Infuse a laid-back feel into your ensemble by sporting a pair of casual boots. During the winter season, when functionality is imperative, it can be easy to surrender to a less-than-stylish outfit in the name of practicality. But this outfit is a shining example that you can actually stay toasty and remain stylish at the same time in the winter season. If you're frequently worried about dressing your age, this ensemble is a tested option.