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Daringly Dapper: Our Ultimate Men’s Dress Shoe Guide

A POV view of a man’s dress shoes

As a company that carries nearly every type of men’s dress shoes imaginable, we decided it would be a great idea to create a men’s dress shoe guide to help our customers make informed purchases.

While one’s style is a very personal thing, it’s wise to know the rules — even if you plan on breaking them! Whether you’re putting together the perfect ensemble for a formal event or looking to elevate your office wear, knowing how to style your footwear is a must. Dress for success every time with this handy guide to men’s dress shoes.

Learn Your Dress Shoe Anatomy

Before we deep-dive into each type of men’s dress shoes, it’s important that you understand the basic structure of a dress shoe, as each distinct style is largely based on the construction and arrangement of each component.

Dress shoes have many parts, but there are four main parts that determine their categorization. In order from front to back:

  • Toe: Self-explanatory. It’s the front of your shoe. Changes in the shape, stitching, and overall design of the toe play a major role in how the shoe is categorized.
  • Vamp: The vamp is the section above the toe and below the laces that cover the front and side of your foot. If you punt a football, you’re hitting it with the vamp (but don’t do that with any type of men’s dress shoes).
  • Facing: The part of the shoe that holds the laces is called it's facing.
  • Quarter: The quarter is the rear part of the shoe that covers the rear side and back of your foot.

Now that you know the terminology, you’ll be able to use this men’s dress shoe guide to identify the differences that make each style unique.

Oxfords & Derbys

Oxfords and Derbys are the quintessential styles found in offices everywhere. They’re very similar, with one slight difference: Oxfords have closed lacing, which means the shoe’s facing and quarter are placed under the vamp. Derbys have open lacing, which means the shoe’s facing and quarter sits over the vamp.

Both types of men’s dress shoes serve similar purposes and can essentially be styled the same, although Oxfords are generally considered to be a bit more formal. That said, both styles can be worn casually as well — they’re quite versatile. As a general rule of thumb, Oxfords work best with a suit and tie or other business attire, while Derbys are a great choice for slacks and a button-up or sweater.

Note: Dress boots are very similar to Oxfords in design, only with higher shafts.


A close-up of brown tassel loafers

Loafers are slip-on shoes that are similar to driving moccasins and smoking slippers, only more formal. There are variations of loafers based on unique decorations called saddles. For example, the iconic penny loafer has a slit, while the tassel loafer has, you guessed it, a tassel.

If you’re looking for a type of men’s dress shoe that lets you flaunt your sock collection, loafers are a solid choice due to their low cut. They look fantastic with a pair of cuffed or cropped chinos that sit right above the ankles. They also work surprisingly well with a pair of jeans.

Monk Straps

Next up on our men’s dress shoe guide, we have monk straps — a shoe that’s less formal than Oxfords, but more formal than Derbys. They’re similar in design to both styles, but they’re unique because they use one or two buckles instead of laces. Monk strap shoes tend to be more attention-grabbing than other styles, so they work very well with bold, edgy outfits. If you’re going to wear this type of men’s dress shoe, go all-in with the look.

Chelsea Boots

Commonly associated with The Beatles and British mod styling, Chelsea boots are laceless, slip-on boots that go up to the ankle and usually have plain, rounded toes. These boots are minimalist in design, but they do attract the eye. They’re quite versatile, as they can be paired with jeans and a tee or a business casual outfit, but they work best when worn by very fashionable, dapper gentlemen with a little edge to their look.

Chukka Boots

Chukka boots are ankle-length boots that can be identified by their minimalist design that features two or three lace eyelets on each side, and little else. They can be classified as a type of men’s dress shoe, but they definitely lean on the more casual side — you wouldn’t pair them with a suit. These types of casual boots look smart with khakis and a button-up, so they’re a great choice for looking and feeling comfortable and relaxed in an office setting.

Other Variations

A pair of burgundy dress shoes with brogueing

Hopefully, this men’s dress shoe guide has made it easier to identify different types of shoes. There are also some design choices that apply to most dress shoe styles that you should know about. Here are the big ones:

  • Plain Toe: The toe and vamp sections are clean and straightforward.
  • Wingtips: Wingtips have a leather overlay on the toe in a “W” shape.
  • Cap Toes: Cap toe shoes have a leather overlay that’s sewn straight onto the top for a capped look.
  • Brogueing: Brogueing refers to tiny, ornamental holes in the leather. There are full brogues, semi-brogues, quarter brogues, and longwing brogues, depending on the amount of brogueing on the shoe. See the photo above for an example of brogueing.

Shop High-Quality Dress Shoes for Less

As you can see, there are plenty of options when it comes to choosing the right dress shoes, and we’re here to make your shopping experience fun, easy, and affordable. We carry traditional dress shoes, as well as dress shoes in every color you can dream up. We also offer a massive variety of materials, sizes, and styles, so don’t hesitate to get in touch if you need help finding a specific type of men’s dress shoe. Look smart and shop smart at Just Men’s Shoes!


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