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The Ultimate Men's Dress Shoe Guide | Loafers vs Oxfords vs Derbys

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Photo Credit: @MrJunHo3

Many men find that choosing footwear can be complicated and confusing and dress shoes are of no exception, but it doesn't have to be such a challenge. There are so many different styles of men's footwear, and they all make different statements. Learning how to match your shoes adds in an extra layer of complexity as well.

The most basic thing to know is about dress shoes is that Oxfords are formal and versatile, while Derby shoes are less so. Loafers are less formal, comfortable and summery, while dress boots make a great autumn wardrobe piece.  Yes, there are a lot of types of dress shoes - we'll go over each and the differences between them.

When putting together an outfit, a man should first determine how formal he needs to look. From there, he is free to play around with footwear styles that match where he is going and what kind of statement he wants to make so that he can pick the right option from his dress shoe collection.

Men's Dress Shoe Details

These details may seem small, but when you’re choosing your dress shoe, it’s important to look for the details that will help improve and enhance your style. 



Look at the toes on your shoes, since the simpler you go, the more elegance you usually have. That’s why shoes like the Oxford, Derby, or Chelsea boot will have no toecap. You can also get a cap toe though, which is an extra toe on the edge of your shoe that will look great for any business environment.

You can also add a little style to your shoe with a semi-brogue design, which is perforated and often serrated at the edge. This will make your look stand out just a little more, but if you want the full detail, you can go for the full-brogue look. With a wingtip, this will especially boost your overall style.


You can look for your chosen shoe with wingtips as well, which will extend along each side of the shoe. They add a little style to your look while still being perfectly appropriate for a business setting.

Along with wingtips, there’s also the longwing brogue that will extend a little down the sides of your shoes. This will meet right at the center seam of the heel to give you a classy look on whichever shoe you choose.

Toe Style

You can make another choice when it comes to your shoes too: the style of the toe. Pick out a rounded toe for something more elegant, or there’s the chisel toe option that’s a little squarer. This makes it elegant yet in something like a Chelsea boot, it’s a little more visible.

No matter what kind of style and construction you end up choosing though, you should be able to find an amazing pair of shoes that fits your style with all of these options below. The only question is which style of shoe will work best for you. Check out below to learn more about the certain types of shoes that you can choose from to match your outfit and still display your style. 

Types of Men's Dress Shoes

Formal Lace-Up Shoes 

black oxford cap toe dress shoe close up

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Oxford and Derby shoes are the two types of men’s formal lace-up shoes and go with formal attire. They share many of the same features, including a Goodyear-welt construction and a vamp. However, there are differences between the two shoe styles.

oxford vs derby dress shoe infographic

Oxfords are a classic, elegant style that originated in Scotland. A good pair of black Oxfords are pretty much any man's go-to formal dress shoe and should be worn with dress pants. Oxfords are sleek and clean in design and feature a "closed lacing" with shoe flaps sewn under the seam directly below the laces and also bound together.

Derby shoes are a little bit more versatile and can be worn with a variety of clothes, including suits or jeans, but are traditionally worn with trousers and a sports jacket. The lacing and shoe flaps on Derby shoes are sewn on the outside, making them more of a robust look. Unlike Oxfords, they come in a variety of colors.

The question is how to wear your Oxfords. This is a popular form of shoe because of how minimal it is, so you can pair it with any outfit. Pick out your Oxford in a color that will work for your outfit. You can even choose leather shoes or suede and pair your shoe with a bright-colored sock to add a little to your style. If you’re going for a business look though, you’ll want to choose darker colors, and stick to black leather shoes when you wear a tuxedo. 


Derby shoes are a little bit different than the Oxford, but you can wear and style them the same way you would style an Oxford. These shoes are a little more casual though, so you’ll want to wear these kinds of shoes with some comfortable and fun socks to help your style stand out.

These shoes were originally a sporting and hunting boot around the 1850s though. But by the 1900s, these were the shoes people would wear out of town. It makes sense too since Derby shoes have a wider fit that will feel more comfortable on your foot. 


mens dress shoe suede loafers

 Loafers are a great option that come in a variety of styles to dress up or down as you like. Loafers have no laces and just slip on, making them more similar to moccasins. They come in a variety of colors and are usually leather or suede and frequently adorned with decorations like tassels and buckles, but sleeker designs and neutral colors are more commonly accepted for formal wear. 


Formal Boots

dress shoe leather closeup

A dress boot is a sleek, often minimalistic, and make a great addition to any outfit, including jeans, trousers, and even certain suits.



chukka desert boots closeup

Chukka boots are casual, ankle boots made from suede, calfskin leather, or even black leather. With crepe (a type of rubber) soles, Chukka boots are also referred to as Desert boots, but Desert boots should not be paired with a suit for formal wear. 



chelsea boots at rock concert close up

Chelsea boots are an iconic style featuring side panels that can add a fun, rock-and-roll twist to a formal outfit. They can be worn with just about anything, from your most exciting suit to your comfortable jeans and flannel shirt. Chelsea boots are known for their comfort and their elastic strip on the sides to make them easy to slip on. 

There are definitely a lot of people out there wearing dress boots these days, and why not? They look amazing. But it’s all about when to wear it. For instance, you want to be careful about wearing them with a suit, and only do so if they’re a nice neutral color that will complement the suit. Try to avoid suede with a suit too, but with boots like the Chelsea boot, you can go casual. Wear these boots with jeans, and keep them only for casual wear. The same thing goes for Chukka boots, which you should pair with a smart-casual ensemble.

Formal Pumps


In our guide to men’s dress shoes, we can’t forget about the Formal Pumps, which have been a prime choice since the 1800s for black-tie events. These are a little like the loafers in that you just slip them on, although you’ll wear these for more formal events. Usually, these are made with shiny black leather, and are very simplistic, making them perfect for pairing with a tuxedo.

Monk Straps

Monk strap shoes are a relatively old style, originating with monks who were experimenting with footwear as an alternative to sandals. The style has evolved to now be a great asset to a man’s formal wardrobe. 

mens formal monk strap dress shoe

When it comes to formality level, they are between an Oxford and a Derby, with an Oxford being slightly more formal and a Derby being slightly less so. Monk straps will always stand out thanks to the bright and bold buckles.

Single-strap shoes are more minimalistic, timeless, and can be worn more leniently. Double-straps, on the other hand, are a bit bolder and are meant to make a statement. The double-strap style is frequently embellished with a decorative toecap. 

Men’s Dress Boots with Jeans

When the temperatures start to drop and the autumn season begins to set in, many men struggle with putting together smart, elegant outfits while also staying comfortable and warm. 

The good news is that the selection for men's boots are endless, and many boot styles can be worn with a pair of jeans. This means that you get to stay warm and comfortable while also looking classy and put together. 

mens chelsea boots close up

Chelsea boots are some of the most versatile boots out there and are a definite staple in any man's wardrobe. This is because Chelsea boots can be appropriately worn to the office and then carry into the evening for a night out on the town. These boots are relatively narrow and come in lighter as well as dark tones. Because of their slender shape, they work best with a slimmer cut of jeans.



casual chukka boot close up on bike

For the man looking for an even more casual option than the Chelsea boot, the Desert boot is a comfortable style that was designed for functionality. Desert boots were designed for World War 2 soldiers who needed a lightweight, comfortable alternative to their combat boots for fighting on sandy terrain.

Today, Desert boots add a vintage look to any outfit. Dress them with a pair of vintage-style jeans and a light jacket and you have the perfect casual fall-time look for a stroll in the park. 

Loafers vs. Oxfords


Oxfords are a great go-to for a man’s first pair of dress shoes. They are very popular, versatile and can be worn with a variety of outfits to a variety of events and occasions. Oxfords can be worn with a man’s most professional business suit, or with a sports coat to a more casual event. 

plain toe black oxford dress shoes

Plain Toe Oxfords

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Oxfords also come in a variety of different decorative dress shoe styles. The most simple are plain toe Oxfords that can be worn with anything from a suit to a pair of jeans.




plaintoe oxford dress shoe in black

Cap Toe Oxfords

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 Cap toe Oxfords are a formal style that are typically worn for black-tie events and church.




light brown wingtip oxford dress shoes

Wingtip Oxfords

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The most casual Oxford style are decorative wing-tip oxfords that look best with jeans.


brown loafers close up lounging

Loafers supposedly originated with King George VI, who wanted a comfortable house shoe. Loafers today, however, are far from simple house shoes and make a perfect, comfortable embellishment to the dressed-up man. 

Loafers aren’t quite as versatile as Oxfords, but they make a fashionable and bold statement, especially in summer wear. They can be dressed up or down as you like and can add a high-class look that will set you apart. 


Wearing men’s footwear doesn’t have to be a challenge. There are a few basic styles to know, including Oxford, Derby, Loafers and formal boot styles. Which formal shoes you choose largely depends on what you’re going to be wearing them with. Now that you know how to wear them don't forget to learn how to match your socks.

It's also important to be creative. Don't be afraid to play around with different levels of casual and formal wear and pick shoes that adequately match the formality of your outfit.