8 Different Types of Dress Shoes

Different Types of Dress Shoes
Photo by Jason Briscoe

From classic Oxfords to Opera pumps, picking a shoe to fit your style from the different types of dress shoes is far from slim.

Wearing the right shoes can turn any boring outfit into a sophisticated one. Even if you are a person who wears sandals and shorts, shoes are essential.

Shoes over dresses enhance any outfit, whether casual or formal. Not only are the best dress shoes for men stylish, but they’re also practical.

Different occasions have different formalities, and the same goes for dress shoes, as some are more elegant than others.

What Are Dress Shoes?

What exactly is a dress shoe? I see this term often and hear how people use it, but what is it? A smart shoe? Slippers? And do I need one?

One man’s tuh-MAH-toe is another man’s tuh-MAY-toh, just as one man’s fridge is another man’s refrigerator.

The same goes for pants and slacks, suspenders with flip-flops, and thongs.

So it is with the different types of dress shoes. According to the American definition, a dress shoe is anything other than a sneaker, boot, or any style of shoe that reveals your feet, such as a derby, Oxford, brogue, or monk-strap shoe. But the average Briton will tell you these are “smart shoes.”

Everyone wants to look their best and put their best foot forward by wearing the best shoes, but not everyone is aware of how to do so.

You wouldn’t want to have fashion failures in the middle of a formal event.

Worse still, you wouldn’t want to spend a fortune on a shoe from the most expensive clothing brand only to go out of fashion within months.

Different shoe styles are suitable for different occasions and clothing combinations. Some shoes should only be worn at festive events, while others should never be worn at black-tie events.

Fortunately, this guide will help you prevent fashion mishaps in the future by giving you lists of the different types of dress shoes and how you can combine them with your daily outfits.

It’s easy to become overwhelmed by the hundreds of combinations. A little guide to the different types of dress shoes for men will show you what you need and, more importantly, what not to choose when choosing shoes.

Many different dress shoes are suitable not only for different tastes but also for other occasions.

It is essential to know what, when, where, and why your dress shoes or you will end up looking ridiculous like the coworker that’s always in black shoes and white socks.

Different Types of Dress Shoes

1. Oxford Shoes

The Oxford shoe is also known as the Balmoral. As the most popular of the different types of dress shoe styles, you can find them in most retail stores.

The characteristics of every Oxford shoe are a low heel and a closed toe. Its lacy eyelets are under the vamp, forming a V-shape.

In addition to the main features, there are different design materials; some Oxfords have a plain toe, while others have a design such as cap-toe or brogue.

Oxfords are your standard go-to office shoe for an interview, a formal dinner, and more. Oxford shoes have a modern, clean, and elegant look. 

There are two stories about the origins of Oxford dress shoes. The first story is that the shoes dating back to the 19th century were popular among Oxford University students. But the shoes were shaped like half-boots, the Oxonian.

Another story is that the shoes come from Scotland, and they got their name from Balmoral Castle. Oxfords may have existed before the 1800s, but they became popular then.

In most situations, the beauty of such a timeless and extensively worn shoe is almost unique. The Oxford shoe can be worn for various events by simply changing the color. Black for more formal occasions and brown for less formal occasions.

Although Oxford is exceptionally versatile, white socks are always prohibited and are never recommended in combination with jeans.

However, Most dress pants will go perfectly with a basic pair of Oxford shoes. If you want to elevate a button-up shirt and trousers or find the perfect shoe for a suit, go with Oxfords.

2. Derby Shoes

Derby type of dress shoes are like Oxfords and are usually interchangeable. But Derby shoes are less formal than other different types of dress shoes and have a few differences.

Derby shoes have open laces, and the eyelets are above the vamp instead of below, like Oxfords. Make flaps visible. The open lacing system allows an adjustment, making Derby shoes more comfortable.

They’re also known as Blucher or Gibson. Because Derby shoes have a more casual look, they are more versatile and go with simple and smart outfits.

If you are going for an unstructured blazer with jeans, wear Derbys. Increasingly formal, stick to Oxford. The specific design of Derby shoes varies. They may have brogueing, wingtips, or cap-toes. When you wear Derby, you will have a refined look.

3. Loafers

If you’re a well-dressed man but short on time, you’ll find several pairs of these versatile and classic shoes in your closet.

Loafers dress shoes are known for their slip-on styles; they’re perfect for the business traveler. Designed to go with most clothes (no shorts, please!), it’s a timeless pair of shoes to wear.

Also called Penny Loafers, these timeless shoes originated in Scandinavia in the 1800s and are known worldwide. Their fast, comfortable, and formal design makes them popular among men worldwide.

The formality of a pair of loafers depends on the material and the design. From sleek leather loafers to lighter suede loafers, the flexibility of these shoes is endless. Leather loafers with metal buckles are more formal than suede tassel loafers.

When leather loafers are paired with a low socks, you can wear them in the office or on formal occasions. Patterns in lighter colors are perfect for slipping it on and going out while maintaining an elegant look.

When it comes to versatility, penny loafers are the best. In summer, you can wear them with jeans, chinos, trousers, or linen pants.

They’re sleek and show off your sense of style, and they hide well as you can quickly slip them on 30 seconds before you walk through the front door.

4. Monk Straps Shoes

Unique for a belt that replaces laces, the Monks is one of the different types of dress shoes, but this time with a few more rules.

However, the lightweight buckle belt system isn’t as formal as the Oxford, making them ideal for business travelers. Monk Strap shoes fall somewhere between Oxford and Derby regarding formality.

As the name suggests, Monk belts were initially the footwear choice of European monks dating back to the 15th century, who favored the secure yet quick function of the buckle.

They wore this style of footwear when working in the field. Monk belts today have belts with single, double, or triple buckles on top.

These designs have been adapted for men’s formal shoes and are ideal for a wide range of semi-formal work wear. 

Traditionally, a shoe designed for the average workplace often comes with a toe cap to provide an extra layer of protection.

If you want to choose monk-strap shoes for an outing, make sure you have tailored pants. Pants that are too wide and too long will catch on the buckles.

Monk strap shoes are perfect with suits, chinos, or jeans. Plus, they’re not formal enough for a tuxedo. Although these shoes don’t have laces, don’t substitute them for loafers on shorts; wear them only with long pants. They will add the perfect amount of charm and elegance to your clothes.

5. Chukka Boots

Chukka boots were initially worn as casual wear in the UK in the 1940s. Today the tradition lives on, and boots can still be seen in formal and informal wear. The open lace design and ankle length make this comfortable shoe more diverse.

They are most often made of calfskin or suede. The eyelets are the main feature that differs from other types of dress shoes. The eyelet on chukka boots is usually in two or three pairs.

If you want to wear chukka boots as shoes, you must wear the right ones. Look for those slender silhouettes. The sole should be thinner and the toe area narrower.

If your chukkas have a thick soles, keep them for casual wear. A pair of chukkas with a thinner sole provides versatility as you can dress them up or down. Please do not wear them with a tuxedo. Instead, the ideal is semi-formal and lower on the scale of formality.

6. Dress Boots

For centuries, dress boots have been a stylish choice with their roots in the Victorian era. Simple ankle boots are a popular choice for a sleek look while maintaining a minimalist style.

The design resembles an Oxford or Derby shoe. Dress boots usually have either a longer shaft or a side zipper.

Paired with your casual wardrobes like pants, chinos, or dark jeans, they retain their sleek, classic look and are practical in harsh weather like cold or rainy weather.

They will protect your feet from the weather while giving you a modern look. As versatile as they are, they are not recommended for use with suits or tuxedos.

7. Chelsea Boots

Are known for their simplicity, these pull-on boots are a quick, slip-on alternative to dress boots. Chelsea boots have a stretchy side that makes them stand out amongst the different types of dress shoes.

In addition to the difference, the side panel and the pull-up tag allow you to put on and take off your boots easily.

Its first appearance on the fashion scene dates back to 1837. They are the invention of Queen Victoria’s cobbler. But the original intention was to walk and ride horses.

In addition to royal and equestrian debuts, the Chelsea boot has been popular in London. The Beatles, Rolling Stones, and Daniel Craig all wore trendsetting boots.

They are usually made without any decorations, making the clean look versatile. They are easily combined with jeans and can add a unique touch to your outfit.

8. Formal Pumps (Opera Pumps)

Formal pumps, also known as Opera Pumps, have been the choice of footwear at black-tie events since the 19th century.

Like loafers, they are laceless slip-on, providing comfort and convenience. However, Pumps are reserved for the most formal events.

Typically in shiny black leather and adorned only with a grosgrain ribbon on the hood, the simple and elegant design is meant to be paired with tuxedos.

Other terms that we should be aware of in the different types of Shoes

You may also have heard of brogues. Slightly confusing, brogues are different from the men’s dress shoe types; they are decorative items.

Irish and Scottish laborers first wore them in the 1800s, shoes with perforated holes that were thought to allow water to flow when the wearer walked on boggy ground.

There are several types of brogue dress shoes for men:

  • Full Brogue: Also known as wingtips, these very decorative shoes, the brogue, start at the top and taper down the shoe’s sides, creating a wing effect. The Full Brogue is a bold choice and is not usually combined with casual clothes like jeans.
  • Half Brogue: invented by John Lobb Company, the half brogue has a perforated medallion pattern on the front of the shoe, located on the toe area and along the seam. Half brogue can be seen in many types of formal footwear.
  • Quarter Brogue: These shoes have a minimum number of perforated details in the seam of the cap.
  • Longwing: a more casual option, Longwing Brogue mimics Full Brogue. However, it extends over the entire shoe. Recognizable by its W-shaped brogue, it is generally over derbies and is not designed for very formal events.


Your entire outfit and the occasion determine the type of dress shoes you will choose to wear. Now that you know the different types, you can always wear a smart casual suit or dress and look stylish.

If you want a pair of different types of dress shoes, consider Oxford shoes as the first option. You can wear them to the office, on a date, at an interview, or at a wedding. Also, make sure always to polish your dress shoes to make sure you look your best.

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