An Easy-To-Understand Guide To Popular Men’s Dress Shoe Styles

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Grey oxford shoes

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Learn the differing styles of men’s dress shoes and you’ll be that much more ahead of the game.

Men’s dress shoes make a statement about their owners.

Gucci Deal Sleds for the finance bros, Belgian loafers for suiting up, intentionally obnoxiously embroidered Stubbs and Wootton slippers for the charity party circuit set, the list goes on and on.

Your shoes should be as nice as you can afford because they’re definitive style statements that speak to your aesthetic and are a tenant of first impressions, but if you can’t shell out hundreds of dollars on new kicks it’s completely understandable.

Men’s Dress Shoes: The Sole of the Power Move

Life isn’t solely a series of business meetings and cocktail parties, it’s schlepping to work and the grocery store and emotional obligations to your family and friends and whatever Hinge match you’ve dredged up that week.

You have other priorities, but it doesn’t hurt to have some aspirational essentials and extras in your closet as an ego boost and definitive middle finger to the status quo.

No one needs to know you snagged a quality pair off eBay or grabbed brogues from your dad’s closet.

The magic of sophisticated shoes is that they can be resoled, or at least preventatively addressed, so they have a longer lifespan that helps justify their cost.

I’ve always been an advocate for buying essential wardrobe items you love and know you’ll wear for years to come rather than replacing “meh” shoes every year because the quality reflects the price.

There are tons of variations of men’s dress shoes, but the main thing to remember is there are two types of formal lace-up shoes – oxfords and derbies.

Oxfords are the fancier iteration because they have closed laces, and the derby is more casual with an open lace.

The more noticeable bells and whistles a shoe has, the less formal it becomes. For example, if you need an elevated shoe for a wedding, a patent black leather oxford is perfect because it’s the most minimal you can get.

The following is a short primer on dress shoe basics, but if you want to investigate further, I defer to David Coggins, author of Men and Style, on all things menswear related.

Formal Men’s Dress Shoe Styles

Oxford

If you need dress shoes for work, weddings and the like, a patent black leather option should be your first purchase—they’re sleek and complement dress pants well.

Defined by a low heel and closed laces, they can come with cap toe, wingtip, a whole cut or plain toe options.

Derby

businessman clothes shoes

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The derby is exceptionally similar to the Oxford save the lacing is on the outside of the shoes, making it look less formal.

You can snag them in just about every fabric and can dress up denim while Oxford should not.

Loafers

Pair of Stylish Expensive Modern Leather Black Penny Loafers Shoes

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The ultimate in versatility, it’s a damn shame if you don’t have a few loafer options in your closet.

A slip-on option that ranges from more formal to casual, loafers are offered in an array of styles including the penny, tassel, and ubiquitous Gucci loafer.

If you want to immediately dress up denim and a polo or button-down, throwing on loafers is the simplest solution.

Less Formal Men’s Dress Shoe Styles

Brogue

Black brogue Mens Dress Shoes

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A brogue is when there’s perforations or embossing of the shoes, usually found on the toe or sides.

Monk Strap

Among the easiest to spot, monk strap dress shoes sport either a single or double strap. The single strap being the slightly understated of the duo.

Monk strap dress shoes really hit their stride (I’m sorry) the past few years with the proliferation of #menswear bloggers littering fashion week.

Plain Toe

This means there’s no defined toecap, making it more streamlined and formal. The more minimal a shoe, the more formal it appears.

Cap Toe

A cap toe contains an extra piece of leather, adding an additional element and making the shoe less formal.

Wingtip

This iteration of a toecap extends to the shoe’s sides like, you guessed it, wings.

Whole cut

This is when the upper is cut from a single piece of leather. Make its patent leather, and you’ve got a stable formal shoe for everything from the office to your wedding.

Kiltie

A kiltie has a tongue of fringed leather, usually on a loafer or monk strap. This power move isn’t for the faint of heart, but it evokes old school cool.

Some of my favorite loafers have a kiltie fringe, and it’s an easy fix when you want to add personality to denim and a button-down.

Tassels

Like the kiltie, a tassel option evokes more of an old world, preppy feel but can dress up an otherwise nondescript loafer.

Slippers

Streamlined, slip-on options that go well with suits and are for more formal occasions when you want to evoke personality. Perfect for a cocktail party or a creative black tie wedding.

Sarah Solomon is a writer in NYC, and you can follow her on @sarahsolfails or her self-parody account, @urbanJAP. Pre-order her book Guac is Extra But So Am I: The Reluctant Adult’s Handbook here.

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