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Even guys that are well-versed in the world of sneakers and fashion-forward men can be at a loss when it comes to buying dress shoes. That’s because dress shoes, and formal attire in general, have historically been more informed by convention and old-school rules than by taste, trends, or personal preference.
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That’s not to say personal preference doesn’t have its place in suiting. The way Bryan Ferry wears his suits is very different from, say, Tom Ford. And Ford’s tailoring choices are pretty different from A$AP Rocky’s, for that matter. But before you can wear tuxedo jackets with hiking boots a la Ralph Lauren, it’s worth first learning the rules.
An Oxford is the most traditional, classic dress shoe choice. Derbies are Oxford’s more casual, slightly rebellious sibling, and penny loafers are typically the most laid-back dress shoe style. Of these three classic styles, the right derby or penny loafer can look great with the best jeans or chinos, but most Oxford shoes will look out of place with anything but dress pants.
As for color, one of the simplest ways to get it right is to avoid wearing shoes that are much lighter than the suit. A tan shoe will look out of place with a dark navy suit, but a richer blue looks good with a darker brown shoe.
To make things easier (or more complicated, depending on how you look at it), we broke down some common dress shoe styles and how to wear them to make it easier to find the best dress shoes for men.
Men’s Dress Shoe Styles, Explained
There’s a wide range of men’s dress shoes, and they vary considerably in terms of style and formality. Even in today’s dressed-down environment, it’s still important to be mindful of which styles are appropriate for which setting. That’s why we’ve broken down some of the most common types of dress shoes, and many of them can be found on our list.
Oxford: Arguably the most traditional style, Oxford shoes are characterized by “closed lacing” with eyelets under the vamp instead of on top, creating a more streamlined and formal look.
How to wear it: Oxfords look best with a traditional suit and are too formal for jeans.
Derby: Derby dress shoes are similar to Oxfords, but they have “open lacing,” with eyelets on top of the shoe.
How to wear it: Derbies are slightly more casual than Oxfords, and many derbies are versatile enough for suits as well as jeans or chinos.
Wingtip: A wingtip can be an Oxford, a derby, or even a boot. They’re characterized by stitching shaped like a wing, and they often have an ornate perforated medallion design on the toe. The perforation itself is called broguing.
How to wear it: Wingtips are more casual than plain-toe Oxfords, and you can wear some wingtips with more casual pieces.
Loafers: Loafers are among the more casual shoe styles still commonly worn with suits. They’re laceless shoes that are meant to be slipped on. They come in various types, including penny and horse bit.
How to wear it: Loafers are inherently more casual, but they still look fantastic with a suit. You can also wear more casual penny loafers with jeans too.
Tuxedo shoes: Tuxedo shoes are often made from patent leather, which has been coated to have a high gloss finish. They come in lace-up or loafer styles. Another kind of tuxedo shoe is the velvet Venetian slipper.
How to wear it: Patent leather tuxedo shoes should pretty much only be worn with a tuxedo.
Dress boots: Dress boots are short boots with a more pointed silhouette than taller, round-toe work boots. They come in lace-up, Chelsea and wingtip styles.
How to wear it: Dress boots look great with a suit or jeans. If you’re wearing them with a suit, make sure the pants drape nicely over the boots’ shaft, and the boots don’t create lumps under the pants.
While usually finding the perfect dress shoe takes a little time, we’ve compiled a list of the best dress shoes for men that are great in nearly all types of settings for almost every foot.
Allen Edmonds Park Avenue Oxford
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The Park Avenue Oxford is a traditional option from a classic American shoe manufacturer, and it’s available in various shades of black and brown. Despite its classic look, it’s a comfortable shoe, coming in second in our most comfortable dress shoes piece.
GH Bass Larson Weejuns
Jeans, chinos, suits, and even shorts — loafers are truly the shoes that can do it all, and Bass is the brand that can best lay claim to creating the slip-on penny loafer. They’re an old-school shoe that’s back in style in a big way, and they’re an affordable option for everyday.
Bruno Magli Maioco Leather Oxford
This classic style is handmade in Italy with a Nappa leather upper and has the perfect not-too-pointy, not-too-round shape. The blake-stitched sole means these shoes can be re-soled by your local cobbler after it wears down.
Johnston & Murphy Jameson Longwing
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Like Cole Haan, Johnston and Murphy uses an unconventional ribbed rubber wedge sole. Johnston & Murphy’s take is more subdued and classic, but still supremely comfortable.
Florsheim Sorrento Wingtip Oxford
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Florsheim consistently delivers when it comes to value and these wingtips are as versatile as they are comfortable thanks to a cushioned footbed and rubberized details on the soles.
Alden Cordovan Plain Toe Blucher
Alden was founded in 1884 and is one of (if not the) most respected American shoemakers still in business today. Yes, these shoes are expensive. But with premium cordovan leather construction, a Goodyear storm welt, and made-in-America manufacturing, these shoes are a worthwhile investment.
Cole Haan Longwing
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You’d have a hard time getting away with these in a conservative office, but Cole Haan’s cushioned sole works with more casual outfits. They’re comfortable, too, notching the top spot in our roundup of the most comfortable dress shoes.
R.M. Williams Men's Boots
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If your office overlooks a ranch, go for R.M. Williams, a brand so Australian it enlisted Hugh Jackman as its global brand ambassador. But the refined leather and streamlined silhouette make it a great option to wear with tailoring.
BEST APRON TOE
Bally Leather Derby Shoes
Bally’s offering is a prime example of high-grade materials with a timeless look. It has an apron-toe, a more unique alternative to the classic cap-toe.
Beckett Simonon Dowler Boots
The Dowler Boot is constructed from a whole-grain, Argentinian leather that shines and cleans like no other with a Blake-stitched sole for easy future repairs. The leather is sturdy but soft enough to support your ankles comfortably and develops a gorgeous patina the more you wear it.
Grenson Camden Leather Derby Shoes
The British know a thing or two about tailoring, and Grenson is a classic English shoemaker. Though the brand has lately become known for messing with convention, they also nail the classics, like this derby dress shoe.
THE DESIGNER PICK
Gucci Jordaan Bit Loafer
The Gucci Jordaan Bit Loafer comes with a luxury price tag, but damn, if this isn’t the perfect loafer for dressing up and dressing down. The horsebit is a design feature developed (and perfected) by Gucci.
Ace Marks Cap Toe Oxford
The shoes are incredibly flexible and don’t take much time for a foot to warm up to the shape, and the regular fit is roomy without being boxy. They’re available in a range of sizes, although some are sold out at the moment.
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