Pairing a brown waistcoat with navy wool dress pants is a nice pick for a classic and classy look. To infuse a more laid-back touch into your ensemble, introduce tassel loafers to this outfit. During the winter season, when comfort is essential, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. However, this outfit is a bright example that you totally can stay toasty and remain equally stylish in the winter season. Wondering how to dress as you pass the big four-oh? This combination is an amazing example.