What to Wear to a First Date: Men Over 40

For a first date dinner or drinks, men over 40 should anchor their smart casual look in well-fitted pieces that communicate intentionality without trying too hard. A tailored blazer or sport coat over a quality knit polo or button-down creates polish, while avoiding the stiffness of a tie. Prioritize structured shoulders and a defined waist in your jacket, as proper fit through the torso reads as confident and put-together in this setting.