How to Choose a Dressier Shoe

by Scott Wagner

Loafers or laces? What about boots? Don’t worry, we’ve got you covered. 

When it comes to footwear, nothing can make or break an outfit quite like a dress shoe. Unlike something more casual, like a sneaker, quality (or lack thereof) is more evident with dressier shoes, so it’s important to consider the materials and lean in to trusted brands. 

Nothing cheapens the look of a fine suit like a loafer that looks plastic. In a similar vein, it’s also important to take care of more formal footwear with polish and yearly cobbler runs. Most dress shoes are made of leather — even the soles — so you’ve got to keep them tuned up like you would a vintage car to avoid an unsightly breakdown. Oxfords with scuff marks or a hole in the sole? No matter what the shoe, these are the kinds of JV moves you want to avoid. 

Here, we’ve rounded up five styles of dress shoes for every occasion, price point, and personality. Scroll through for our picks that run the gamut from cool and classic to traditional with a twist. 

The Oxford 

To a certain set, a suit should never be worn without Oxfords. (See Savile Row.) Originally created in Scotland, it’s a two hundred year old design named after the educational institution where they were most frequently worn. Though there’s no “right” shoe to wear with a suit, the Oxford is a solid no-frills choice that’s never not appropriate. Recognizable by its closed lacing system, cap toe, and eyelets under the vamp, it’s a classic shoe that’s sleek to the point that it’ll always feel contemporary. 

Cap-Toe Oxford, Jack Erwin, $225,

The Brogue 

Brogues are like the Oxfords punk cousin. Heftier, heavier, and highly ornamented, they’re an eye-catching shoe that look as good with pinstripes as they do with a jacket and jeans. Though they’re just for decoration now, the holes that dot the face and seams were originally perforations that allowed water to drain during walks through bogs and wetter land. The evolution of function…be bold and go Brogue. 

Polished Binder Oxford Brogue, Church’s, $790,

The Loafer 

Loafers are an easy way to dress up a more casual outfit or suit that’s not made of wool. In other words, if the invite says “business casual,” go with a loafer. We like a classic Weejun (pennies optional) as it’s a versatile style that works with trousers and a sweater, a corduroy suit, or a white t-shirt and your favorite pair of Levi’s jeans. 

Logan Flat Strap Weejun, G.H. Bass, $110,

The Chelsea Boot 

Wearing a boot with a suit is a fashion-forward move made famous by the Beatles. Key here is to go with a leather pair and polish them frequently. Wear them with a slim suit, a tuxedo, or a white dinner jacket…but take care to shine ‘em up. Because boots are already more casual in nature, even the slightest scratch or scuff will make it look like you reached for the wrong pair and’ll totally kill your look. 

Leather Ankle Boot, Gucci, $1,250,

The Wild Card 

A shoe comfortable enough to be called a “slipper” that also doubles as your drink order? Sold. 

Velvet Slipper, Stubbs and Wootton, $525, 

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