This semi-casual combination of a crew-neck sweater and a white and red dress shirt is super easy to throw together without a second thought, helping you look seriously stylish and ready for anything without spending a ton of time searching through your closet. When this ensemble appears too classic, play it down by slipping into a pair of white leather low top sneakers. Seeing as temps are starting to drop, this ensemble appears a smart option for the season. When it comes to casual dressing ideas for over-40 gentlemen, this combo looks nice on almost any gentleman.