Pair a gilet with a crew-neck t-shirt to create a seriously stylish and modern-looking off-duty outfit. Why not take a more relaxed approach with shoes and add a pair of beige athletic shoes to the equation? Rest assured, this ensemble will keep you snug as well as looking dapper in this transeasonal weather. Relaxed outfits for 40-year-old gentlemen aren't actually that hard, as you can see.