Wearing the right shoes can take any outfit from boring to sophisticated fashion. Dress shoes elevate any outfit, whether it’s casual or formal wear. The best dress shoes for men are not only stylish but practical as well.

Everyone wants to put their best foot forward and in their best shoes, but not everyone knows how. You wouldn’t want to have a fashion faux-pas in the middle of a formal event. Worse yet, you wouldn’t want to spend a fortune wearing the most expensive clothing brand’s shoe only for it to go out of fashion in a few months.

Different shoe styles suit different occasions and outfits. Some shoes are only to be worn to formal events, and others should never be worn at a black-tie event. Thankfully, this guide will help you prevent any fashion mishaps in the future.

The best types of dress shoes for men
The best types of dress shoes for men

Take a look at eight timeless types of dress shoes that every man should have in their closet. They give a classy look to any outfit.

8 Best Dress Shoes for Men

Dress shoes should remain ageless and work with almost any style of clothing you wear. Whether that style is formal, casual, or anything in between. Black or brown dress shoes with a sleek leather or suede finish are always a safe bet.

1. Oxford Shoe

Oxford shoes are a good starting point when you’re buying a dress shoe. It is a basic shoe that is so versatile that it can be worn almost anywhere. Depending on the color and style, they can be dressed up or down.

The shoe gained popularity in the 1800s among Oxford University students. The aim was to exhibit one’s status at the time. 

The most recognizable characteristics of an Oxford shoe are the closed lacing, low heel, and long toe. It comes in four different styles, but the most common style is the Cap Toe Oxford. This style of shoe is most often worn as business attire or for formal occasions. 

Black leather cap toe Oxford men's shoes
Black leather cap toe Oxford men’s shoes

2. Derby Shoes 

Derby shoes are often confused with Oxford shoes. They are quite different once you know their distinct characteristics. Derby shoes, unlike Oxfords, have an open lacing system. 

This means that the vamp (section on top of the shoe that covers the foot) splits in half and laces.

The wider, more comfortable lacing makes this shoe more casual. The smooth leather designs give any outfit a polished look. A plain derby is the most versatile option as it can be a formal or casual dress shoe.

Men's black leather Derby shoes
Black leather Derbys are popular dress shoes for men

3. Chelsea Boots 

These laceless boots are minimal and timeless. They originated in the 19th century and gained popularity in Chelsea in London, which is where they got their name. They have been a classic staple of men’s capsules wardrobes ever since.

Chelsea boots are traditionally made of leather but can be found in suede as well. The silhouette of the boot is the strongest pulling point. 

The Chelsea boot is tight-fitting and cut right at the ankle to avoid adding any bulk. The elastic side panel on the shoe gives them a comfortable fit so that you can spend all day in them.

Men's tan leather Chelsea boots
Men’s tan leather Chelsea boots

4. Loafers 

The origins of the Loafer are a bit fuzzy because there were different variations of the shoe worn throughout many cultures in history. Native Americans wore a similar shoe to the loafer called moccasins. Fishermen in Northern Europe also had a variation of the shoe.

Loafers are versatile slip-on footwear with nine different styles of shoes. Penny loafers are the most versatile type out of the nine categories.

Black diamante leather lace-ups

The other types of loafers are horsebit, kiltie, driving, slipper, boat shoes, bit loafer and espadrilles. Bit loafers were invented by Aldo Gucci in the 1960s and feature a piece of metal across the vamp.

Tassel loafers are a popular choice for business attire or weddings. The dapper shoe matches well with long pants, slacks, or shorts for a smart casual look. However, black tie and loafers do not mix style-wise.

Men's blue suede loafers with a rope buckle
Men’s blue suede loafers with a rubber sole

5. Dress Boot

Dress Boots are slim and have a dressy look that is similar to an Oxford or Derby shoe. They have been in style since the Victorian era and are still a fashionable option worn by many today. They are great shoes to wear during the cold winter months because of their high ankles. 

Dress Boots are more on the casual side of footwear and are not recommended to wear with suits or tuxedos. These boots pair well with casual wear like jeans or slacks. They instantly add some sophistication to an otherwise bland outfit.

Tan brogue leather dress boots
Tan brogue leather dress boots

6. Monk Straps 

Monk Straps originated in the 15th century by European monks. They wore this style of shoe while working the fields. Modern-day Monk Straps have single, double, or triple buckled straps across the top of them.

A single strap shoe is the most formal out of the bunch because of the lack of detail which creates a sleeker look. This easy slip-on shoe is more formal than a loafer. Just use a bit of this shoe shine, and you can wear monk strap shoes to formal events.

A pair of Monk single strap cap toe dress shoes
A pair of Monk single strap cap toe dress shoes

7. Chukka Boots

Chukka Boots were originally worn as casual wear in the United Kingdom during the 1940s. Today, the tradition lives on and the boots are still seen in both formal and casual attire. It is the open lace and ankle-length design that allows this comfortable shoe to be more versatile in style.

A Chukka Boot can be a formal or casual shoe depending on the silhouette you choose. A slim silhouette is best for formal wear because of the simplicity of the style.

A chunky sole will make the shoe more casual and laid-back. These popular men’s boots look good in both leather and suede.

Nubuck leather brown men's chukka boots
Nubuck leather brown men’s chukka boots

8. Opera Pumps

Opera Pumps are formal slippers from the 19th century only worn with evening wear. They are typically black in color and adorned with a bow on the top. The shoe is typically made with quilted silk or black patent leather with a high gloss finish. 

Although not as popular today as in the Victorian era, these dress shoes will certainly elevate any formal wear. They are standard shoes to wear with white tie attire but are acceptable to wear to black-tie events as well.

Men's patent court shoes
Men’s patent court formal shoes

Final Thoughts on Men’s Dress Shoes 

You may have also heard of brogue shoes. Somewhat confusingly, brogues aren’t actually a type of men’s dress shoe, but a decorative feature.

First worn by Irish and Scottish workers in the 1800s, brogues have perforated holes which were thought to originally enable water to drain out when the wearer walked on boggy ground.

There are several types of brogue dress shoes for men:

  • Full Brogue – also known as wingtips, these highly decorative shoes feature a pointed toe cap with extensions in a W shape.
  • Half Brogue – invented by the John Lobb company, half brogues have a perforated medallion pattern at the front of the shoe.
  • Quarter Brogue – these shoes have a minimal perforated detail on the seam of the cap.

Dress shoes are an ageless staple every man should have on their shoe rack. The right shoe, shirt collar, pocket square and a luxurious watch can make you look effortlessly stylish.

Full brogue Oxford leather shoes
Full brogue Oxford leather shoes

Most dress shoes can be either formal or casual, like an Oxford Shoe. Others, like an Opera Pump, can only be worn to special events. The more you know about dress shoes, the better your style can be. 

Whether you prefer a plain toe or a more decorative style, these eight classic dress shoes will have any man feeling their best no matter what they wear.

Interested in luxury men’s style? Check out these other luxury style features:
Best Bespoke Tailors | Best Luxury Luggage Brands | Best Luxury Watches for Men | How to Choose a Suit | Preppy Mens Style Essentials

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The best types of dress shoes for men
The best dress shoes for men

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