Written by Wesley Kang

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 and when thinking about oxford and derby shoes is that oxford shoes are formal and versatile, while a derby shoe is slightly less so, but still serves a formal function. Loafers and other slip-on shoes are even less formal, more comfortable and summery, while dress boots make a great casual attire piece and can make you look taller.

 

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. While oxford vs derby shoes may look identical at a glance, some of the details below may set them apart.

 

Shoe Design

Look at the overall adornments on your shoes. Generally, the less decorative features and simpler the shoe is, the more formal the shoe is. The toes on your shoes can be telling: the simpler you go, the more elegance you usually have. Simple designs like plain or a cap toe are generally featured in more formal footwear like an oxford shoe, derby shoe, even loafer shoe.

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, called wingtips.

It's important to note that the adornments on dress shoes aren't exclusive to shoe types like oxford and derby shoes. In fact, an oxford shoe could have brogue elements and so could a derby shoe.

Wingtips

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. Wingtips can be seen on derby and oxford shoes and not exclusive to either.

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. Wingtips are not exclusive to a shoe type and can be featured across different types of shoes including oxford shoes, derby, and even boots. Brown wingtips look great with paired with a blue suit.

 

Shoe 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, a cap toe for a refined formal look, or there’s the chisel toe option that’s a little squarer. These toe styles are typically seen in an oxford shoe, derby shoe, and sometimes a loafer. 

Comparison Summary

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. If the occasion is formal, go with an oxford or derby shoe. If the occasion is casual attire, or somewhere in between, go with either derby shoes, or dress boots.

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 - Derby vs Oxford

Photo Credit: Carets.com

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

They may look really similar on the surface, but there are some important details that differentiate the two. See our infographic below for distinctive traits between an oxford shoe and derby shoe:

Oxford Shoes

The oxford shoe is a classic, elegant style that originated in Scotland and considered the quintessential formal shoe. A good pair of black oxford shoes 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 system with shoe flaps sewn under the seam directly below the laces and also bound together. A high quality oxford shoe also often features a leather sole with this closed lacing system.

The question is how to wear your oxford shoe—its minimalism exudes a classic formality and elegance. Traditionally, an oxford shoe with its closed lacing system and its leather sole is worn with a 2 or 3-piece suit in an appropriate color. Pick out your oxford shoe 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

The Derby shoe is 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, known as an open lacing system, making them more of a robust look. Unlike Oxfords, they come in a larger variety of colors and with a leather sole.

A Derby shoe is a little bit different than the Oxford, but you can wear and style them the same way you would style an Oxford. This open lacing system is 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.

Derby shoes were originally designed for sporting and hunting purposes around the 1850s. But by the 1900s, these were the shoes people would wear out of town. It makes sense, since Derby shoes strike a good balance between traditional menswear and comfort with its open lacing system and leather sole. 

Semi Formal and Casual Men's Shoes

Loafer

Loafers are a great option that come in a variety of styles to dress up or down as you like. In many cases, a loafer can still be considered a formal shoe. 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. 

 

Men's Dress Boots

A dress boot is a sleek, often minimalistic, boot that is constructed of leather or suede and make a great addition to any outfit. Dress boots can include typical adornments like toe cap design, wingtips, brogue features and can be worn with most outfits including with jeans, trousers, and even certain suits.

 

Men's Casual Boots

Chukka Boots

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. Here's a list of our favorite chukka boots.

 

Chelsea Boots

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. We researched the best chelsea boots for men here.

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.

 

Loafers vs. Oxfords

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 and is supposedly named by Oxford University students. Oxfords can be worn with a man’s most professional business suit, or with a sports coat to a more casual event. 

 

Photo Credit: Carets.com

Plain Toe Oxfords

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, along with some nice dress socks. 

 

 

 

 

Photo Credit: Carets.com

Cap Toe Oxfords

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

 

 

 

Photo Credit: Carets.com

Wingtip Oxfords

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

Loafers

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. 

Conclusion

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. 

If you liked this article, check out our other guides on the best boat shoes and how to clean shoes.