The 20 Best Men’s Dress Shoes in 2023

While menswear has become more casual — white leather sneakers with summer suits, for example — it still pays to own a variety of the best dress shoes for men, especially if you’re heading to a formal shindig or need to accessorize your men’s workwear collection. Here’s the key, though: Dress shoes needn’t be uncomfortable, and there are simple steps you can take to find your perfect fit. Yes, it’s actually possible to look sharp while enjoying a smooth, comfortable ride underfoot. To get started, pay attention to a shoe’s basic details, says Brad Schaeffer, DPM, a foot and ankle surgeon and expert podiatrist at New York City’s Central Park SOLE. 

“Look for a dress shoe with a wide toe box, removable insole, and soft leather,” says Schaeffer, as the wide toe box will relieve pressure on the foot. “If you can find ones with removable insoles, you can put an insole with arch support and comfort inside,” noting that Dr. Scholl’s is his go-to for insoles.

For comfortable material, Schaeffer says soft leather is a must, while people should avoid synthetic materials if at all possible, as they don’t offer much “give” or flexibility. Schaeffer notes that an insole could be the most important factor in finding a properly fitting, comfortable pair of stylish men’s dress shoes. 

“Our feet are our body’s natural shock absorbers. Having a great insole is paramount,” says Schaeffer. Arch support is also important for added cushion, no matter your stride type. And crucially, finding a pair of the best men’s dress shoes needn’t be wildly expensive. At the minimum, look for full-grain leather with clean, straight, tight stitching. Here you’ll find some prime examples of our favorite styles that you can stand in all day.

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Derbies

There are plenty of varieties of stylish dress shoes for men, and the derby is a fine casual option meant to be paired with jeans, corduroy pants or other slightly more informal trousers. The key difference between a derby and an Oxford is the construction and lacing system. Derbies feature open lacing, or shoelace eyelets sewn onto the top of the upper (or “vamp”), making them wider.

  • These toe capped, no-frill Derby Oxford hybrids come in wide sizes and at an unbeatable price.

  • An athletic outsole and heat-activated insole give this shoe performance technology in a stylish package.

  • Burnished leather gives these shoes a distinctive look, while tan goes nicely with blue denim.

  • Ethically handcrafted by artisans in Guatemala and fully resoleable with a stacked leather heel.

Oxfords

Oxford shoes are a dressier step up from the derby shoe, and the difference once again comes down to lacing and design. Unlike derby shoes, Oxford shoes feature a closed lacing system that creates a more streamlined, dressy effect. This makes Oxford shoes more narrow, and also more apt for wearing with traditional suits and formal wear. 

  • Dressy black leather with shine elevates these above the rest, as does the handsome cap toe stitching.

  • Deep brown suede is distinctive, and since it’s water-repellent, you can wear these frequently to work.

  • Allen Edmonds has plenty of heritage and pedigree, and the brogue detailing is a timeless touch.

  • Your favorite boot brand now makes highly accessible, streamlined dress shoes in rich leather.

Loafers

Loafers exude an air of refinement and classy style. And the best loafers for men are easy to wear, with a slip-on design that should prove comfortable and breezy. Loafers are at their best when paired with warm-weather suiting, or else elegant picks like linen trousers and a knit polo.

  • Buying sharp loafers doesn’t have to cost an arm and a leg – this is designer quality on a budget.

  • The insole is the crux of stylish loafers, and this pair features Ortholite cushioning built right in.

  • Rich leather and an upper void of stitching give this pair some minimal, versatile class and style.

  • A flexible leather upper and rubber sole work in tandem to give you a light-as-air feel and refined look.

Dress Boots

Dress boots are a slightly more rugged alternative to dress shoes, yet still built with the same sense of refined style. Dress boots come in varieties ranging from lace-up options to a variety of designs, like the best ankle boots for men. Dress boots are ideal for styling in the fall and winter, thanks to their added traction and next-level durability in inclement weather.

  • An EVA midsole and cushioned footbed team nicely with a sturdy, all-season rubber outsole.

  • There’s lots to love about this classic pair, from finely crafted leather to the shock-absorbing insole.

  • Yes, dress boots can still be rugged, as with this effortlessly cool pair that’ll age handsomely.

  • Dress these luxurious leather boots up with a wool suit, or down with chinos and a chambray shirt.

Monk Straps

The monk strap rests somewhere between a timeless lace-up pair of dress shoes, and the refined loafer. Named for the single or double-buckle straps on the upper, these shoes also boast an additional layer of material (held in place by those straps). They’re a popular style in warm weather with linen suiting or breezy dress trousers.

  • Eye-catching bordeaux leather gives these shoes a premium look and feel, as does brogue toe detailing.

  • Made-in-Portugal construction makes for a streamlined design, and polished leather is a dressy touch.

  • The details make the difference, from the smooth single-monk strap design to brogue cap toe perforations.

  • Invest in the very best with this splurge-worthy pair, one built with 200-plus steps.

What is the most comfortable type of dress shoes for men?

Dress shoes, no matter how stylish, seem to get a bad rap — but there are ways to choose your dress shoes with comfort in mind. Brad Schaeffer, DPM, a foot and ankle surgeon and expert podiatrist at New York City’s Central Park SOLE, advises to focus specifically on finding a pair of soft leather shoes with a wide toe box and a removable insole.

“I feel the most important thing is the insole,” Schaeffer says. “This will allow your feet to be supported and stabilized every step you take.” The wider toe box, meanwhile, relieves foot pressure and provides a comfortable ride underfoot. As for shoe inserts, Schaeffer notes that Dr. Scholl’s works well as an insole, provided your dress shoes have removable insoles of their own.

Arch support and comfort are crucial, and the right insole delivers on that functionality, whether you have flat feet or high arches, Schaeffer said. 

“I like to have some cushion in my dress shoes because a lot are very rigid,” Schaeffer added. 

What makes a dress shoe formal?

A dress shoe is, by definition, more formal than a pair of casual sneakers, but there are still a few keys that make a dress shoe formal. For starters, premium leather with a shiny, polished finish will appear more formal than shoes made from burnished or broken-in (or hand-finished) leather, which often has more texture and character. 

Events like weddings call for shoes made from premium full-grain leather without noticeable scuffs or marks. The same ideal stands for dress shoes in business formal settings, like when worn with a suit. Still, more business casual workplaces are an apt time to break out your favorite dress shoes. 

For example: A pair of brown leather dress shoes or boots, particularly with brogue detailing or more casual burnishing, work nicely with a classic business casual ‘fit of tan chinos, light blue Oxford shirt, and a lightweight navy blazer. That same combination works effortlessly with blue jeans in most settings, too. 

Beyond that, clean black or brown leather loafers or lace-up dress shoes are ideal for weddings, particularly if wearing a timeless suit in a shade of charcoal or navy (leave the tuxedo to the groom and groomsmen, unless the dress code calls for black tie). No matter how you wear them, it pays off to have a pair of the best dress shoes for men in your rotation.


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