Fashion

A Definitive Guide to All The Kinds of Dress Shoes You Should Know

From cap-toes to brogues to boots.
IMAGE Dina Litovsky
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We love a good sneaker just as much as the next guy, but there are those times when only a classic pair of dress shoes will do the trick. And thanks to their timeless good looks, you know they'll serve you well for the years to come. Here are 10 styles that every man should know as we roll into fall.

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1| Brogues

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. Strandmok cap-toe oxfords by Allen Edmonds

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2| Cap-Toe Oxfords

The quintessential dress shoes. Get them in black and invest in quality, because they're never going out of style. Chelsea oxford shoes by Edward Green

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3| Monk Straps

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. Your call. Grant double monk shoe by To Boot New York

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4| Penny Loafers

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. Ravello penny loafers by Gucci

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5| Chukka Boots

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 ge the job done just fine. Desert boots by Clarks

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6| Chelsea Boots

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. Finn Chelsea boots by To Boot New York

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7| Plain-Toe Derbies

Bonus points if they've got a little texture of a chunkier sole (both of which you'll find on the pair here). Think of them as the rugged coousin of those black cap-toe oxfords—and be sure to style them accordingly. 508H derbies by Saint Crispin

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8| Dress Boots

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. Jarman Leather boots by Paul Smith

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9| Longwings

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. Sid longwing brogues by Grenson

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10| Split-Toe Derbies

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. Dover Burnished-Leather derby by Edward Green

This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.

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