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The Seven Types of Dress Shoes Every Man Should Own

From oxfords to monk straps, these are the dress shoes that are worth breaking in.

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Last Updated December, 2017.

Long a product of the highest craftsmanship and design — from wizened men in Turkey to cobblers in Western New York — shoes are your connection to the ground and a sign that you care about the small details (or you don’t). If you invest in a quality pair and take good care of them — by cleaning, polishing and storing them on a cedar tree — they’ll last for years, with the occasional repair. From oxfords to monk straps, these are the dress shoes that every man should own.

Oxfords


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The oxford is characterized by lace eyelets that are attached below the vamp, as opposed to open flaps as with the derby. This leads to a closed seam above the tongue, and a sharp, neat look.

Park Avenue Cap Toe Oxford by Allen Edmonds $395

Connaught by Crockett & Jones $635

Dubai Polished-Leather Oxford Shoes by Church’s $650

Derbies


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Unlike the oxford, the derby has an open-lace construction. The eyelets are sewn on top of the vamp for a slightly bulkier, looser look.

Cadet Derby by Common Projects $525

Daniel Creased-Leather Derby Shoes by Trickers $645

Derby Shoe Tan Horsehide by Viberg $710

Driving Shoes


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Also known as a moccasin, the driving shoe is the modern version of traditional Native American footwear. It often features rubber tabs on the sole for a touch of elegance, formality and versatility without any sacrifice to comfort.

Antique Calf Driving Shoes by The Original Car Shoe ~$400

Gommino Suede Driving Shoes by Tod’s $445

Horsebit Suede Driving Shoes by Gucci $480

Brogues


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Decorative and elaborate meets sturdy and traditional with the brogue. It’s primarily characterized by its low heel and multi-piece construction, which gives it a layered and detailed look. The perforations may not work to drain water on a stomp across the marsh as they were originally intended, but they will certainly catch the eye.

Ludlow Semi-Brogue Oxfords by J. Crew $298

Archie Triple Welt by Grenson $505

Adam Pebble-Grain Leather Oxford Brogues by George Cleverly $700

Loafers


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Characterized by its simple laceless design, the loafer comes in many styles, from the slitted penny to the tasseled tongued slipper.

Chocolate Suede Bowtie Loafer by Founders $298

Country Loafer by Yuketen $438

Shell Cordovan Pinch Penny Loafer by Rancourt & Co. $650

Bluchers


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Named after a late-18th-century Prussian field marshal general who commissioned the first boot of this style for his troops, the blucher is fit for war. Or, more appropriately, a business-casual event. Don’t confuse it with the more formal oxford, which has a closed connection between the vamp and laces.

Plain-Toe Blucher by Jack Erwin $195

Plain Toe Blucher by Carmina $450

Meadow Plain Toe Blucher by Alden $550

Monk Strap


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Fear not the broken lace. The distinctive strap replaces the laces on these newly back-in-style shoes. Like the buttons on the suit jacket you’ll wear with them, the monk shoe comes in one- and two-buckle styles.

Bristol Suede Monk-Strap Shoes by O’Keefe $530

Burnished Leather Monk-Strap Shoes by Santoni $1,100

Wiiliam Leather Monk-Strap Shoes by John Lobb $1,300

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