Shoes
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.