|Strandmok cap-toe oxfords ($295) by Allen Edmonds,|
Brogues actually started out as hard-wearing shoes for men trudging through Irish bogs—the holes allowed water to drain out. Now, the broguing is purely decorative, and the shoes are equally at home in the office and the countryside.
|Chelsea oxford shoes ($1,220) by Edward Green,|
The quintessential dress shoes. Get them in black and invest in quality, because they're never going out of style.
|Grant double monk shoe ($395) by To Boot New York,|
Single- and double-strap varieties are equally acceptable, though the latter feels a little more modern. A cap toe isn't strictly necessary, but it does help to balance the lines of the upper.
|Ravello penny loafers ($630) by Gucci,|
Your grandfather probably didn't wear penny loafers with a suit—they were considered too informal for business settings. But that doesn't mean you're bound by the same conventions. Go ahead and slip a pair on under a slim-cut two-button.
|Desert boots ($124) by Clarks,|
Think of them as your workhorse shoe. They'll go well with jeans, but you can just as easily wear them with a suit. (And you should!) They're a little too casual for conservative offices, but for most modern workplaces, they'll get the job done just fine.
|Finn Chelsea boots ($395) by To Boot New York,|
Brown suede may be the move if you're looking to wear your Chelseas with jeans, but when we're talking about the right pair to match with a suit, you can never go wrong with sleek, simple black.
|Derbies ($1,035) by Norman Vilalta|
Bonus points if they've got a little texture or a chunkier sole (both of which you'll find on the pair here). Think of them as the rugged cousin of those black cap-toe oxfords—and be sure to style them accordingly.
|Jarman Leather boots ($595) by Paul Smith|
Look for something sleeker than the work boots you bust out on the weekend. That means polished leather and a lower profile, like you see on the combat-boot-inspired pair here. Feel free to wear them on the weekend as well—suit not required.
|Sid longwing brogues ($335) by Grenson|
A riff on the classic brogue, the "wings" of the wingtip extend from the toe all the way around the shoe, meeting at the back. Oxford versions exist, but you're more likely to find them in derby form. It's just a bit more casual, but no one's going to fault you for wearing them to the office.
|Dover Burnished-Leather derby ($1,415) by Edward Green|
Sometimes, you want to shake things up a bit. That's where the split-toe derby comes in. Its aproned toe adds visual interest to a classic style that's a little different than the shoes everyone else at the office is wearing.