For a casually cool outfit, pair a tobacco turtleneck with grey wool chinos — these items play really well together. Feeling venturesome today? Shake things up by rounding off with a pair of black leather casual boots. During winter, when warmth is above all, it can be easy to settle for a less-than-stylish outfit. This outfit, however, proves that you totally can stay warm and remain equally stylish during winter. When it comes to style tips for 40-something gents, this look looks great on almost any gentleman.