The Gentleman's Ultimate Guide to Men's Dress Shoes: Types, History, Tips, and Timeless Elegance

The Gentleman's Ultimate Guide to Men's Dress Shoes: Types, History, Tips, and Timeless Elegance

Some critical aspects must be mentioned when discussing men's fashion and style. One of these things that will make a modern-day gentleman stand out as both fashionable and stylish is his shoe game, a common term in men’s fashion conversations.

The choice of shoes is the distinguishing factor between a sharp-looking man and the average dresser who doesn't care much about their appearance (which we should, as how you look speaks volumes; it is the first impression someone gets before we even talk). In an outfit, shoes are the devil in the details, and they will make or break your look.

In this article, we'll explore dress shoes in more depth and discuss everything you need to know to achieve timeless elegance in your shoe game.

What Exactly Are Dress Shoes?

The definition of dress shoes can be simplified as any type accepted as formal. Dress shoes are the direct opposite of athletic shoes such as sneakers. The extent of formality might change from one fashion expert to another. For most fashionistas in Britain, dress shoes can be worn in a black tie or a white-tie event- on the extreme side of formal. In America, dress shoes also mean footwear worn with formal outfits, but this definition also captures shoes worn as part of bright casual/ business casual outfits.

Given the different but related views on what exactly a dress shoe is, at HolloShoe, we have defined dress shoes as a blend of both. Any pair of shoes that is fit for formal and smart casual events can be accepted as a dress shoe.

Now that we understand what qualifies as a dress shoe let’s unravel all you should know about the different dress shoes for men.


When it comes to dress shoes, oxfords are number one. Oxfords are considered the most formal type of dress shoes. You will see them in black ties or white tie events. For any event that requires strict adherence to a formal dress code, oxfords are your go-to shoes. Also known as Balmorals, they are a must-have for any gentleman.


The History of Oxford Shoes

It is unclear where the Oxford shoes originated, but two theories attempt to explain this. One of the most popular theories states that these shoes got their name from their geographical origin, Oxford.

In the early 19th century, students at Oxford University wore knee-high boots that were buttoned rather than having laces. Later, around 1825, these boots were trimmed down to create something closer to the modern Oxford; they were referred to as Oxoniana by then. By the end of the 19th century, this shoe had evolved to create what we now know as Oxford shoes.

The other theory states that before Oxford University students adopted the shoe, it had originated from Balmoral Castle. It was first custom-made for Prince Albert of Aberdeenshire, Scotland, who wore laced-up boots. It is believed that the Oxford we see today was an adaptation of Prince Albert's shoes for hunting and running.

What Are the Distinguishing Features of Oxford Shoes?

Oxfords are classic and timeless dress shoes that can help you effortlessly achieve that dapper look. So, what makes them stand out and differentiate them from other dress shoes? Here’s what to look for in an Oxford dress shoe:

  • Closed lacing system- the main differentiator
  • High-quality leather/ suede
  • Structured construction
  • Sleek Silhouette

Today, Oxfords are the epitome of formal footwear and are best suited for business attire, weddings, and other formal occasions. Black Oxfords are the most formal, while brown pairs offer versatility for both casual and formal wear. Pair black Oxfords with a well-tailored suit for a classic and polished look. Brown Oxfords can be paired with chinos or dress trousers for a smart-casual aesthetic. 

Derby Shoes

Also known as Bluchers in the U.S., Derby shoes epitomize versatility and elegance. When it comes to formality, they come in second after Oxford shoes. Although inclined more towards the formal dress code, Derby shoes can be worn in smart casual settings.

What Is the History of Derby Shoes?

Derby shoes, believed to have improved Oxford shoes to accommodate more comfort and different foot types, can be traced back to the mid-19th century. They are believed to have drawn their inspiration from Prussian General Gebhard Leberecht von Blücher's open-lacing boots, which he wore with his troops. The Derby shoes we have today blend the Blucher boots and Oxford shoes.

What Are the Distinguishing Features of Derby Shoes?

Known for being a little less strict than Oxfords, Derby shoes offer more flexibility. Here are characteristics that tell apart a Derby shoe from other types of dress shoes:

  • Open-lacing system
  • An elongated or round toe shape
  • Casual aesthetic
  • Offering more comfort

For the modern gentleman with a sense of great fashion, Derby shoes are suitable for formal and casual occasions. They can be dressed in a suit or jeans and a blazer, making them a versatile addition to a man's wardrobe. For a sharp office look, pair black Derby shoes with a charcoal or navy suit. Brown or tan Derby shoes can be paired with lighter suits or smart casual outfits for a more relaxed vibe.

Brogue Shoes

Brogue shoes are defined by their high perforation and stylish contemporary touch. They are very similar to Derby shoes in versatility and elegance. However, they are a little bit more casual than Derby shoes and would be frowned upon if worn in a strictly formal event like a black tie.

What Is the History of Brogues?

The brogues we see today have their origins in Scotland and Ireland. They were first worn as a solution for traversing wet terrain. ‘Brogues’ are the holes punched into the leather. The expected use determined the extent of perforation—more holes/‘brogueing’ was adopted for damper areas. This is the explanation behind the name. Although they were first perforated for their functionality, later on, the perforations were adopted as an ornamental element.

Today, the perforations are perceived as what distinguishes them as more contemporary and stylish. This broguing is also seen as an ornamental feature of the shoes. Also, the perforations are decorative and a measure of formality. The more perforations a shoe has, the less formal it is, and vice versa.

What Are the Distinguishing Features of Brogues?

As mentioned earlier, and just like the name suggests, what differentiates brogues from other types of dress shoes is the highly perforated characteristic. Although some oxfords can be perforated and referred to as Oxford brogues, a standard brogue has an open-laced system, unlike the Oxfords. Here's a summary of the distinctive features of brogues;

  • Highly perforated
  • Open-lacing system
  • Smart casual touch

There are various styles of brogues, including semi-brogues, quarter-brogues, and full or longwing brogues. The latter two styles have more perforations and are less formal.

Brogues are versatile shoes that can be dressed up or down depending on the occasion. Full brogues are suitable for business casual settings, while semi-brogues or quarter brogues can be worn with formal attire. Pair wingtip brogues with a tweed suit for a sophisticated, heritage-inspired look. Wear brogues with tailored trousers and a fitted blazer for a more contemporary ensemble.

Monk Straps

Monk straps are characterized by their unique side buckle fastening system feature, which is different from other dress shoes, such as Derby and Oxford shoes, which have a lacing system. Although slightly casual, monk straps can be worn in most semi-formal settings and formal events.

What Is the History of Monk Straps?

How did these types of shoes end up with the name monk? Yes, you guessed right. The original monk straps were worn by men who worked in the monasteries. They were a closed-toe version of the sandals they used to wear. The straps, buckles, and closed features offered more protection and grip for the manual labor they did. The monk straps can be traced back to the 15th-century European monasteries.

With this foundation, the monk strap evolved in style, shape, and make to include more modern features.

What Are the Distinguishing Features of Monk Straps?

Monk straps are distinguished from other dress shoes by their straps and buckle fastening system. This feature makes them easily identifiable and can hardly be mistaken with any other type of shoe. They offer a touch of sophistication, and correctly adding them to your ensemble will leave you standing out as a gentleman who understands his shoe game.

There are two main types of monk straps: the single monk strap (which is considered less formal) and the double monk strap (which is considered more formal than its counterpart, the single monk strap).

Pair them with tailored trousers and a fitted blazer for a polished and sophisticated look. The clean and streamlined design of monk straps complements the sleek lines of a well-tailored suit, adding a touch of elegance to your ensemble. Opt for a classic black or brown pair of monk straps to achieve a timeless, versatile aesthetic that transitions from the office to formal events effortlessly.


Last but not least are loafers, more contemporary dress shoes that strike a balance between formal and casual dress codes. These versatile shoes are mostly considered less formal, so they are a no-go zone when you are attending a very strict formal event.

What Is the History of Loafers?

Loafers have drawn their inspiration from Moccasins, which were originally worn by Native Americans. Moccasins were unique as they did not include a fastening system, whether lacing or straps and buckles. The modern loafer was first created by Wildsmith, a London-based shoemaker, in 1926 and quickly gained popularity, becoming a staple piece in men's wardrobes.

What Are the Distinguishing Features of Loafers?

Loafers are characterized by their slip-on design, typically featuring a low heel and a moccasin-style construction with a separate sole and upper. Some loafers may feature decorative elements such as tassels, a penny slot, or metal horse-bit detailing on the vamp.

Today, loafers have become a staple in the modern gentleman's wardrobe. They can seamlessly help you pull off a dapper, bright, casual look. Pair classic penny loafers with chinos and a button-down shirt for a timeless preppy look. Wear suede loafers with jeans and a polo shirt for a casual yet sophisticated ensemble.


This guide comprehensively covers the critical aspects of every fashionable gentleman's top 5 dress shoes. From Oxfords to loafers, from their history to styling tips, we hope this has been an exciting venture to understand dress shoes for men deeply.

At HolloShoe, we believe in elevating every step with unparalleled craftsmanship in footwear. Check out our vast collection of shoes, from dress shoes to athletic and more casual ones. We are here to elevate your look, comfort, and confidence. Contact us today if you need any more information.



Written by Emmanuel Isaac- Content Writer and Editor at HolloMen

Emmanuel is an experienced freelance writer specializing in fashion. Combining research skills and creative storytelling, he crafts engaging content that's both insightful and stylish. Known for his unique mix of analytical depth and creative flair. ( 

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