Shoes: The ABCs of Men’s Dress Shoes-Oxfords, Derbies, Brogues, Sneakers, Slip-On, Sandals and more


Shoes are a way to let your personal style shine brightly outside the patterned everyday suit or jeans. As a dapper man, you value a nice pair of shoes and consider it  an investment to both your appearance and your wardrobe. Looking presentable is necessary at all aspects of life, whether in a casual or business environment. This guide is going to help you better understand your shoes and take your shoe game to the next level of fashion you never imagined to even exist.

If you are a man who beliefs there aren’t many options for men when it comes to shoes styles, and and feel biased considering all of the options women get, then be prepared to be chocked by all of the knowledge you are about to grasp on your side of the shoe game. After reading this article you will be apt to not only become a shoe guy, but actually a men shoe style coach.

“Be well dressed, behave like a gentleman, and keep your shoes shined.”  – Joseph Abboud


This is how part of this guide dedicated to the fancy shoes, the ones you attend events in, not casually hang out at a bar with friends.

Toe Styles

When it comes to dressier shoes’ toe, there are six distinctive styles that are the most popular and you must know.

Plain Toe Shoes

The simplest of all shoes’ toes. This style consists of an unadorned look great for composing great clean looks. Plain toe shoes are mostly suitable for formal outfits like weddings as they are a perfect match to tuxedo dress pants.

Medallion Toe Shoes

This style contains a simple brogue decoration located at the shoes’ toe.

Cap Toe Shoes

Most commonly seen on Oxford shoes, this style is also available in other styles, although not as popular. The horizontal line crosses the vamp of this kind of shoes.

Wingtip Toe Shoes

The Style is brogue with perforated and serrated at the edges with a winged cap and a single peak located at the middle of the shoes’ toe.

Apron Toe

Apron Toe Shoes have a seam starting from the middle of the toe area which goes around ending in the middle of the shoes. Apron shoes can be oxfords or loafers, the loafers mostly have a tussle on top of the shoe adding to the style flare as seen on the photo above. “It is totally impossible to be well dressed in cheap shoesHardy Amies

Split Toe

This style is an apron toe style with a split beginning at the start of the apron down to the sole.


Broguing is how the perforations made around the seam of the shoe (the style at the toe of the shoe) is called.

Closed Lacing vs Open Lacing

Closed lacing is the shoe made with the face of the shoe sew above the vamp of it, and in the open lacing, it is sewed under the vamp of it.

Type of Dress Shoes

The Derbies

Back in the 1850`s, when hunting was a far more popular sport, this type of shoes was invented as the perfect one to wear to practice the sport. It wasn`t until the 20th century it became an appropriate style to wear to work daily.

Commonly mistaken with Oxford shoes, the biggest difference between the two style lays in the shoe montage where the face in the Derby is sewed above the vamp, making this style known for its wider fit.

The Oxfords

Oxford shoes are known as a more elegant Derby. This classic and timeless style is the modern version of the once just as popular Oxonians. Its face is sewed under the vamp providing a great looking contour of the foot. This piece is a key piece to many looks as it works with almost any.

The Loafers

This slip-on style is not only easy to put on but also to pull off. Invented so that the English King George VI could use it to walk around his property, this shoes were known as casual-only until the 60’s business trend said it could be dressed up when paired with suits. Nowadays, loafers are becoming more and more popular with several styles suitable for cocktails, formal and casual outings.

The Monk Strap

Monk shoes or monk strap shoes traditionally refer to buckled shoes. Growing up, one could rarely find gentlemen dressed in a pair of shoes other than the single monk strap. Nowadays, two buckled shoes, some designers have adopted unusual variations with 3 and more straps have become very popular with some designers going for 3 or more straps. My advice for you as a style enthusiast is to stick with a single or double monk strap as they are going to earn you a sustainable wardrobe in several years to come.

The Chelsea Boots

Supposedly having been invented by Queen Victoria’s Shoemaker, J. Sparkles-Hall, this is not only a comfortable fit but also an easy one to slip on and off. Rather you known this style from The Beatles members or from every Instagrammer Coachella outfit, this ankle length piece is known for its low heel and round toes. This piece adds an alternative edginess to the outfit and is sure to make your outfit become a look.

The Dress Boots

Dress boots are basically a long Oxford most commonly found in leather, but a suede look can also be pulled off with the right outfit style as shown above. Keep in mind when purchasing shoes of this style it is better to stay away from chunky styles as it will give off quite a rustic look, which for a dress boot, it isn’t good.


The Chukka Boots

Created to be worn by polo players after the match, this style resembles the sport official shoes of practice, which are ankle length, with the difference of being shorter. The boots get its name literally from the game, as Chukka is also the name of the unit of time used in polo.

The most common style of this boot has round toes and face above the vamp, like Derbys, made of suede. However, it’s been in the market for time enough to have already gained a lot of different variations.


When it comes to casual shoes, the variety is even bigger. The market is always looking for comfortable options to expand and new styles come out every year.

The Driver or Mocassin

This is the rubber soled version of the dressier loafer. As the name says, they were created to add a grip while driving, ever since has become much more of an everyday wear kind of style. The key to this shoe is to keep it clean and don`t pair it with socks.

The Sandal

The man sandal`s or Mandal’s, have been becoming each time more popular and made in many different styles. When it comes to rubber ones, do keep it on the beach, but for the new not rubbery styles enjoy using it all around during summer, but remember to get a pedicure first!

The Athletic Shoes

The biggest problem with athletic shoe is that most people who do different kinds of exercises insist in only buying one, instead of purchasing one for each type of impact, such as one for running and one for walking, but at the end of the day, just like you would not moisturize your face with a cleanser because it would be bad for your skin, why would you do something just as harmful to your knees?

Low Top Sneakers

The low-cut version of sneakers is usually quite a minimalist one. Sure, you can find them in assorted colors, but that is usually as much of an edge as it gets, making it the perfect shoe for a day by day look having endless possibilities to wear at casual events. This style is the “smart” version of the sneakers.

High Top Sneakers

Originated in sports, the High-Top Sneakers are the Low Top Sneakers’ cool younger brother everyone likes. All the discretion the low top have is thrown right away with such a simple difference as to make it longer – and usually chunkier.

Not only high tops are edgier, but it is also usually substantially more expensive, seeing professional players sign their collections. Even know it start with sports and go along with it for a long way, the style was able to break free from the “sport only” usage implied, having become a common street wear nowadays.

Slip-On Sneakers

The lace less version of sneakers that resembles loafers but are meant to much more of a casual environment wear. Like the low top ones, they are seen mostly as a “smart” style, unlike the high-top ones, but brands have been making it each time edgier by experimenting with new materials and textures. This style could be perfectly placed between the low and high-top sneakers in the edgy to smart scale.

Casual Boots

The casual version of the dress boots, meant for a dressed down look, got its best use in rainy cold days when you need to keep every bit of body warm you can. However, with so many styles in the market this type of shoes have become a staple year around for both men and women.

This type of boots works with every casual outfit out there that aren’t shorts, as that’s the one piece of clothing the boot market still hasn’t perfected a nice style to pair with.


Originally crafted in the Occitania and Catalonia around the 13th century, regions of France and Spain and worn by men and women in the Pyrenees, this shoe style later gained popularity across Europe and became widely known as a warm weather essential due to its flexible sole and lightweight feel. History holds that this easy-to-wear utility shoe in canvas with a jute rope sole used to be considered peasant shoes—now they’re favored by the jet set, and that’s why you’ll see a ton of good-looking offerings from designers across the board.

If you happen to have found this article while shoe shopping, this is the sign you are looking for to purchase the better quality one that will last you longer without deforming. Think of shoes as an investment, especially the ones you like. If you ever intend to buy a low-quality one thinking of replacing it soon, why purchase it in the first place?

What do you think of this article? Did you already know all the shoe style? Let us know by leaving a reply in the comment section below!

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