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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.


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.



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



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


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



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



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



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


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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