The Ultimate Men's Dress Shoe Guide | Types & Styles Explained – Nimble Made

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

Photo Credit: @MrJunHo3

Many men find that choosing footwear can be complicated and confusing, 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 comfortable and summery, while boots make a great autumn wardrobe piece. 

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. 

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. They share many of the same features, including a Goodyear-welt construction and a vamp. However, there are differences between the two 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.


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

Dress boots are 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. 

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 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.