If your dude is already rocking shirts with collars and his leisure look is more Vampire Weekend than casual Friday, you can recommend he ditch his sneaks and try on a pair of slip-on penny loafers like these Bass Weejuns. These have been making a big comeback the past few years and appeal to fellas who are exploring the always-handsome "cool grandpa," "pothead professor," or "preppy hot shot" styles of today. Gently explain to him that polished loafers are just as obnoxious as cement-soled Jordan reissues (in a good way), and if he is open to displaying a little Uptown edge, you would strongly approve.
And for the man for whom the loafer is a no-fly zone, gummy-soled desert boots can be his first solid step to a more grown-up shoe game. A pair of desert boots that have been sufficiently worn in say, "I'm sharp but I'm not trying to be anyone I am not." They are chill, unassuming. They go great with everything from a sweatshirt to a tweed blazer to a polo and don't cost more than a decent pair of gym shoes. Plus, they look even better when they are funked-up and a bit dirty so he won't feel precious breaking his new dogs in.
Bass Weejuns Burgundy Loafer, $89, available at Bass; Clarks Desert Boot, $120, available at Amazon.