A shirt jacket and a red crew-neck sweater: this is it, the look of your dreams. Give an elegant twist to an otherwise standard look by slipping into a pair of brown suede tassel loafers. This one is a good idea when it comes to a kick-ass outfit that will take you from summer to fall. As a 30-something Millennial gentleman, you probably want to start dressing more maturely. In this case, outfits like this are perfect as inspo.