To look like a stylish dandy, wear a waistcoat and navy wool dress pants. To infuse a more casual touch into your ensemble, complete this look with tassel loafers. During winter, when warmth is imperative, it can be easy to settle for a less-than-stylish look in the name of convenience. However, this look is hard proof that you can actually stay toasty and remain equally stylish in winter. This outfit demonstrates that looking fashionable as an over-40 guy is easier than one might think.