The 10 Dress Shoes Every Man Needs to Know This Fall

Now we can all admit that we love a great sneaker, I mean what guy don’t you know has that ever so put together collection of Jordan’s still capsuled in the box as if it’s a trophy or prized procession. With all of that being said there’s also a time and place for everything and all though we love to rock a clean kick from time to time, there is absolutely nothing wrong with rocking a classic shoe to complete your dapper look. Thanks to the dapper men over at Esquire in an article written by: Jonathan Evans, here are ten styles that every man should know as we roll into fall.

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Brogues

Brogues actually started out as hard-wearing shoes for men trudging through Irish bogs—hence the holes, which went all the way through and allowed water to drain out. Now, the broguing is purely decorative, and the shoes themselves are equally at home in the office and the countryside.

Strand cap-toe oxfords ($50) by H&M, H&M.com

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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 ($70) by H&M, H&M.com

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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.

Medford monk straps ($80) by H&M, H&M.com

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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 and rest assured that you’re breaking the rules the right way.

Suede loafers ($70) by H&M, H&M.com

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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 get the job done just fine.

Flex-toe chukka boots ($571) by Alden for J. Crew, jcrew.com

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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.

Bed Stu Tribute Chelsea boots ($165) by Bed Stu, UO.com

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Plain-Toe Derbies

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.

Plain-toe derbies ($60) by Urban Outfitters, UO.com

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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.

Dress boots ($265) by Bed Stu, UO.com

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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, like you see here. It’s just a bit more casual, but no one’s going to fault you for wearing them to the office. (Promise.)

leather longwing brogues ($99) by H&M, H&M.com

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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.

split-toe derby ($50) by H&M, H&M.com

photography by:DINA LITOVSKY

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Mark Pollard

Men's Fashion & Entertainment Writer

A young college graduate of many trades, big dreams and great style. "EffYeahMark": Writing / Photo Taking / Film Making Collective. Stay tuned for my journey and read along as I inform you on the latest in men's fashion and celebrity entertainment, your dope for reading.