For Dressing Up:
Leather shoes ($170) by Florsheim Limited
Forget wingtips. All those swirling perforations are enough to make a man dizzy. Instead, show some restraint with black cap-toe oxfords, as dark and slick as an oil spill. No fuss. No showboating. Just an understated classic.
Dressing Down:
Leather sneakers ($495) by Bally
Save the pumped-up kicks for the gym and think twice about tricked-out high-tops: Opt for one of the countless variations on the all-white leather sneaker in stores right now. Keep 'em clean and wear 'em everywhere.
For the Hours In-Between:
Suede boots ($158) by Banana Republic
A good suede chukka boot, not quite high-top, not quite low-top, and in some variation of light khaki, is as versatile and refined as casual footwear gets.