When the setting permits casual dressing, wear a white and red vertical striped short sleeve shirt with khaki chinos. You can get a little creative with footwear and smarten up your outfit by sporting a pair of dark brown suede loafers. This getup is a safe option if you're on the lookout for a great, season-appropriate getup. So if you need dressing tips for 30-something Millennial gents, this outfit is definitely worth saving for later.