Everything You Need to Know About Men’s Dress Shoes

Pity the poor dress shoe. Like the necktie, the high-tech revolution seems to have left them both behind in favor of hypercool sneakers, plain gray T-shirts, and hoodies,  those ubiquitous uniforms of Silicon Valley. And yet, all things come around again, and as executives find themselves in the spotlight — whether for good reasons or ill — that extra measure of confidence that comes with dressing up a bit can help reel in a new client, and maybe even nab that promotion. 

To build a wardrobe of dress shoes, start with the basics. Choose styles that will look great with a suit. Even if you don’t wear one every day, they’ll still accent dark, work-appropriate jeans, trim-fit khakis, cool dress trousers, and even a clean-cut pair of athleisure pants. Don’t be afraid to spend some cash here, either. These should be thought of as an investment in classic styles that — with some care — will last. Get something that might take a little beating if you were to, say, jump on a bicycle or decide to walk a couple of blocks instead of just hopping into an Uber. 

You’ll never go wrong with basic black and dark brown, but a paler brown or even “nude” color are great when we get into warmer temperatures. Every guy should also have at least one pair of cordovan or burgundy shoes in his arsenal, especially for holiday dressing. 

A note of caution about boots: Do be careful they don’t start to look too “industrial.” We’re not saying that we aren’t big fans of a solid pair of work boots and, even, on occasion, cowboy or engineer boots, but just keep in mind that they aren’t going to have the sartorial edge of these standouts. 

Jack Erwin Baxter Oxford – $235
Jack Erwin Baxter Oxford

Let’s start with truly the most minimal expression of gentlemen’s footwear style, the Oxford. Here executed perfectly by Jack Erwin, the Baxter maintains a simple silhouette, devoid of any ornamentation save its laces and a bit of stitching. It’s practically a slipper. In this case, it’s made from a single piece of leather, joined by a single seam. They are the ultimate expression of “shoe.” 

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Officine Creative Anatomia Derby – $585
Officine Creative Anatomia Derby

The major difference between a Derby and an Oxford is that the panel at the bottom of the laces is open on a Derby, as opposed to stitched down on an Oxford. It’s yet another variation on a minimalist’s statement piece, but Officine’s version offers a bit of an “honest working man’s” feel to it. A perfect pair for your inner (but more confident) Willy Loman, the vintage patina provides a broken-in, comfortable look. 

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Allen Edmonds Park Avenue Cap Toe Oxford – $695
Allen Edmonds Park Avenue Cap Toe Oxford

Building further on the theme, a cap toe grants just the smallest indulgence of interest to a dress shoe by adding a simple line stitched a few inches back from the tip of the shoe. In the burgundy color shown above, Allen Edmonds uses genuine Horween Shell Cordovan Leather, with both leather and shoe made in the USA. 

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Beckett Simonon Yates Oxford Brogue – $199
Beckett Simonon Yates Oxford Brogue

Perforations in swirling, graceful patterns dance across the shoe’s body to create the Brogue which offers a more decorated descendant of our basic shoe. The patterning makes it less formal, but still legal for pairing with suits and ties. At Beckett Simonon, your shoes will be made once you’ve placed the order, allowing the company to save dollars on inventory, and pass those savings on to you. 

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Cole Haan Kneeland Bit Loafer – $300
Cole Haan Kneeland Bit Loafer

While the loafer (by its very name) begins to slide into casual territory, it’s still quite acceptable in most American workplaces, particularly in these days of needing to have shoes that slip on or off easily at the airport. The addition of the horse’s bit harks back to equestrian roots and adds a touch of bling that elevates this style’s character. 

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Bruno Magli Iko Tassel Loafer – $495
Bruno Magli Iko Tassel Loafer

Slipping further and further into casual territory, in some circles, the tassel loafer is practically a sneaker, clearly made to be paired with a pair of gray flannel trousers and a navy blazer. Since that would still be considered pretty dressed up by 21st-century standards, we’ll include them. Maybe don’t grab ‘em if you work at one of the “Big Four” accounting or hyper-prestigious law firms, but they’re perfect for a wedding or to dress up a pair of jeans. 

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Ted Baker Azzlan Derby Boot – $250
Ted Baker Azzlan Derby Boot

Here we move squarely into casual dress shoe territory. Building on the heritage of the Derby shoe, the Derby boot provides a clean look but draws the eye up a bit higher on the ankle. This version from Ted Baker is a home run with jeans or khakis for most offices, but the tonal contrast heel detail makes it a nice play with the tapered trouser of a slim-fit suit. 

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To Boot New York Monk Strap Boot – $398
To Boot New York Monk Strap Boot

In the last few years, the monk strap shoe — roughly based, yes, on a style worn by monks in the Middle Ages — rose back to prominence in men’s footwear. Maybe its look of weight and solidity was a way to keep us psychologically grounded during the “Great Recession’s” dizzying times. They are still considered to be a relatively formal shoe. We like this booted version, though, because it maintains its air of formality with a naughty insinuation of badassery. 

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Florsheim Belfast Side Zip Boot – $135 
Florsheim Belfast Side Zip Boot

The spare, side-zip ankle boot offers a bit of swagger, evocative of the swinging 1960s, and perhaps even a touch of the cowboy. It’s a great look when paired with trousers cut just short enough to celebrate the shape and which may even get caught on the top from time to time. From a trend standpoint, this style lands squarely between the Chelsea boot, with its elastic panel that moved back into prominence a few seasons ago, and the short jodhpur boot, with its ankle strap, that we’re watching for 2019. 

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Hugo Boss Patent Evening Shoe – $398
Hugo Boss Patent Evening Shoe

Most men are going to make it through their entire lives just fine without owning a pair of evening shoes. However, if you happen to work in a profession that requires regular attendance at black-tie events — say in finance, not-for-profit development, or, hey, black-tie event planning — your feet will thank you for having a pair that fit right and is comfortably broken-in. Yes, you can get away with wearing a classic black Oxford or Derby, but why risk those being a bit beaten down when you can have a crisp pair of glossy patent leather gems like these from Hugo Boss ready to roll? You could wear these for everyday, but that may come across as just a bit heavy on the dandy side, but they do look absolutely awesome with a pair of beat-to-hell jeans. 

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Now that you know what dress shoes to wear, you should probably get yourself a nice pair of socks to go with them.

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