4 Types of Dress Shoes for Men

Cropped feet view of model wearing Carlo Mid Terrain Sneaker.

Finding the right comfortable dress shoes can feel like a daunting task. With the right sneakers for men, your dress shoes can be the most versatile staple in your wardrobe, elevating every outfit as your feet hit the ground. 

The ideal dress shoe can help you turn heads whether you’re at a wedding, hosting a dinner party, or simply going for a stroll around the block.

But how do you choose when it seems like there are so many types of dress shoes? Never fear! Consider this blog as your personal stylist for formal shoe styles. In it, you'll be able to try on four different types of dress shoes to help you find a pair that fits the occasion and your personal style. 

#1 Oxfords

As the name might imply, an oxford shoe is a classic shoe elegant enough for the most formal occasion. If you want a single pair of dress shoes, an oxford shoe pair is an excellent option due to their versatility.

The defining characteristic of these shoes is their closed-throat construction. The V-like shape of the quarters—that’s the leather around the laces—differs from the parallel lines of other shoes, making plain toe oxfords instantly recognizable to the trained eye.

Slip into a pair of oxford dress shoes if: 

  • Your personal style is classic and timeless
  • You’re planning to attend a black-tie event
  • You simply want a pair of comfortable dress shoes to accompany a tux

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#2 Derby Shoes

If oxfords seem a little too dressy for your personal style, but you still want a versatile dress shoe, then the derby shoe might do the trick for you. 

Maybe you don’t find yourself in a tux too often, and you don’t need the leather shoes to match. But what you do want is a shoe that will complement most other types of suits, working well both at the office and on your weekends out.

Derby shoe styles fit that bill and are some of the best business casual shoes

The open-throat silhouette of this black shoe distinguishes it from its dressier cousin, the oxford. Wondering about how to lace dress shoes? Remember the leather around the laces we call the quarters? Here, it runs parallel and over the vamp (the upper front part of a shoe).

Slip into a pair of derby shoes if:

  • You’re looking for a black shoe that can run the gamut from business to casual
  • You aren’t planning on attending any black-tie events any time soon but want leather shoes that’ll pair well with jeans, tweed trousers, or any suit other than a tux

Cropped feet view of model wearing the Men's Carlo Sneaker in grey.

The Navi Dress Shoe is TOMS’ modern twist on derby shoes as well. An even more versatile shoe than their more-traditional counterparts has a sneakered sole that makes it casual yet sophisticated for leather dress shoes. 

#3 Boots

You might not have been expecting to find boots on a list of dress shoes for men, but it really depends on the dress boot. A dress boot can absolutely be sophisticated and show-stopping.

A Chukka boots, in particular, comes in a wide range of desert boot styles. Some are decidedly not dressy, while others belong on this list as much as any other shoe. 

A Chukka boot is ankle-length leather boots with open lacing. Look for short desert boot options with a narrow cap toe and a sleek silhouette to ensure that they’re formal enough to be worn with a suit.

Slip into a pair of chukka boots if: 

  • You want to add a little creativity to your formalwear
  • You enjoy a comfy ankle boot that still delivers when it comes to polishing up an outfit
  • If comfort is at the top of your list and you will be standing or walking, a boot may be your perfect choice

The versatile Navi Boot is TOMS’ answer for men who want to dress up while maintaining their outdoorsy style. The ankle boot is water-resistant and lightweight with an OrthoLite® insole for maximum comfort. 

#4 Wingtips

If you like a little more detailing, wingtip shoes have you covered. The perforations that define these shoes are a classic look at home in any formal environment.

Wingtip shoes, also known as brogues, come in many shapes and styles. What defines them is their W-shaped overlay rather than their silhouette. Oxfords, derby shoes, and boots can all be wingtips. Look for their slightly bulkier silhouette and the decorative wings opening up from the shoes’ toes to find what sets them apart from other shoes on the rack.

Slip into a pair of wingtips if:

  • You’re looking to strike a balance between casual and elegant with black or brown shoes.
  • You need black dress shoes that are functional but sophisticated enough to wear to a job interview or a dinner date.

TOMS Dress Shoes for Every Sense of Style

By now, you’re well on your way to figuring out which types of men's dress shoes you’d like to try, whether it is black dress shoes or brown shoes. The good news is that you’re already in the right place to take the next step. From ultimate comfort dress casual styles in canvas or leather uppers, to dress derby shoes to complete your look to basic boots and beyond, we have them all at TOMS.

Our styles are chic enough for any formal setting, and you’ll feel comfortable about your choice as your feet hit the ground too. Looking for something a little more laid-back? Check out our men's slip on sneakers and men’s slippers collections.

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Reviewed By Dan Caves

Dan Caves is the Senior Manager of Digital Marketing at TOMS and has been operating in the digital space for 6 years, writing about the latest trends or styles and helping brands make bold statements with innovative tactics and creative concepts. He's determined to go all the places, see all the things, and pet all the dogs.