5 Pair of shoes you need in your wardrobe:
The Wing Tip:
For Work: Not all wing tips look right with suits. But this pair, with its closed-lace construction, slim leather soles, and rich brown patina, could hold its own with most any three-piece.
For the Weekend: A chunkier toe and a rugged sole are the stuff of casual wing tips and many an action-packed weekend. And if the leather picks up a scuff or two, so much the better.
For Work: You can’t get much more formal than a finely wrought pair of black oxfords, especially when the toe looks like this: not too pointy, not too round, and not remotely square.
For the Weekend: The lighter the shade of brown and the softer the hand of the leather (or, in this case, suede), the better your oxfords will look with jeans, khaki chinos or beat-up cords.
For Work: Opt for black (inherently more dressy than brown), and keep in mind, the finer the construction, the more polished they’ll look. Speaking of: Keep them shiny.
For the Weekend: Look for something unstructured like desert boots (or another spongy-soled variation thereof). They’re just the kind of lightweight knockabouts that downtime requires.
The Monk Strap:
For Work: Rather than the one thick strap you usually find on monk-strap loafers, this version has two thin straps and lighter buckles, both of which make for a little more professional gravitas.
For the Weekend: The thicker the strap, the more casual the shoes. Don’t worry about polishing the buckles, either: The metal’s faded shine is what gives them their character.
For Work: When forgoing laces altogether, a hand-rubbed, artfully shaped pair of look-at-me loafers are just the kind of shoes that command respect. Even at the office.
For the Weekend: Thin leather soles are good for office loafers, but thicker rubber soles are standard-issue for casual loafers. Same goes for a penny slot, which must, of course, remain penny-free.