A Breakdown Of The Most Popular Types of Dress Shoes For Men

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From your standard Oxfords to your Opera Pumps, the selection of men’s dress shoes is far from slim.

Every style, construction, and material has a unique look and an intended occasion.

The hundreds of combinations may seem overwhelming, but this quick guide to men’s dress shoes will show you the do’s, and more importantly the don’ts, of your shoe choice.

Different Types of Styles For Men’s Dress Shoes

The many different styles of dress shoes are not only to fit different tastes, but also different occasions.

oxford and derby dress shoes

It is important to know the what, when, where, and why of your dress shoes, or you might just end up looking as ridiculous as the coworker who wears black shoes and white socks.

Pictured Above: Johnston & Murphy Conard Cap Toe Oxford

1. Oxfords & Derby Dress Shoes

Oxfords are your standard go-to dress shoes for the office, an interview, a formal restaurant, and more. They are sold at virtually every retailer, and function as part of your staple wardrobe.

Its essential characteristic: the laces.

They are known for their smart lace up system. Specifically, the Oxford comes in two basic styles; the Derby and the Oxford. The difference is all in the laces. The Derby features an open-laced system (visible flaps), while the Oxford features the more popular close-laced system (hidden flaps) as seen in the picture below:

derby vs oxford

The Oxfords, originally the Oxonian Shoe, have been popular since around 1825.

How did they withstand the test of time?

Oxfords maintain a simplistic yet elegant design that can be dressed up or down, and is available with many different construction types.

The beauty of such a timeless and widely used shoe is that it is almost a one-type-fits most occasions. By simply changing the color, the Oxford shoe can be used for different occasions. Black for more formal occasions, and brown for lesser occasions.

Although the Oxford is extremely versatile, white socks are still off limits, and it is never advised to pair them with jeans. Most dress pants will fit perfectly with the staple pair of Oxford dress shoes.

loafer dress shoe for men

Pictured AboveGucci Donnie Bit Loafer

2. Loafer Dress Shoes

If you are a well-dressed but short on time kind of man, there are sure to be a few pairs of these versatile and classic shoes in your wardrobe.

Famous for the laceless slip-on design, these are perfect for the traveling business man. Designed to be paired with most outfits (please, no shorts!) they are a timeless grab-and-go pair of shoes.

Ranging from the sleek and formal leather Loafers, to brighter colored suede Loafers, the flexibility of these shoes are endless.

When a leather Loafer is paired with a low-cut sock, they can be worn in the office or to a formal occasion. The lighter colored designs are perfect to slip on and go out, while still maintaining a styled look.

Sometimes still referred to as Penny Loafers, these timeless shoes stem from 1800s Scandinavia, and have made its popularity around the world and through the passage of time. Its quick, comfortable, yet formal design make them popular among men all over the world.

They are elegant and show off your sense of style, and hide well that they are easily slipped on 30 seconds before you left your front door.

double monk dress shoes

Pictured Above: Calibrate ‘Cusano’ Double Monk Shoe

3. Monks

The Monks, unique for the strap that replaces laces, is a dress shoe with a few more rules. Not quite as formal as the Oxford, the easy buckle strap system make them ideal for business travelers.

Like the name suggests, these shoes were originally the shoe choice of European monks who favored the secure yet quick function of a buckle.

This design has been adapted into a formal men’s shoe, ideal for a wide range of semi-formal work attire. Traditionally a shoe made for the average work place, they often come cap-toed to ensure an extra layer of protection.

This type of shoe is not often worn on a casual outing, nor to a highly formal event. However, when worn correctly, Monks are always the centerpiece of your outfit.

single monk vs double monk

Commonly available with one or two straps, the design is secure and fashionable.

Pictured Above: Scout Chukka (left), The Hobe Chukka (right)

4. Chukka Boots

Originally popularized in the 1940s United Kingdom as casual wear, these ankle-high boots have become a unique addition to today’s formal wear.

Most commonly made from calfskin or suede, Chukka Boots feature thin leather soles and rounded toes.

They can easily be adapted to formal wear or casual. The open-laced design usually creates a more casual look, and they are generally not paired for tuxedo-worthy events, however a semi-formal gathering or a work day at the office, these boots are the perfect addition.


Pictured Above: O’Keeffe Algy Split-Toe Polished-Leather Boots (left) Tom Ford Edgar Burnished-Leather Boots (right)

5. Dress Boots

With their roots in the Victorian era, Dress Boots have been a style choice for centuries. The simplistic, ankle-length boot is a popular choice for those who want to look sharp while maintaining a minimalistic style.

Dress boots are extremely versatile, and can we worn with your casual wardrobe such as jeans. When paired with slacks they maintain their stylish and classic look, and are practical for poor weather conditions.

As versatile as they are, they are not recommended to be worn with suits or tuxedos.

Pictured Above: Cole Haan Lenox Hill Chelsea Boot

6. Chelsea Boots

Popular for their simplicity, these laceless boots are a quick, slip-on alternative to Dress Boots.

Slightly less formal, they feature a plain look, with elastic at the ankle for easy dressing.

Originally designed for Queen Victoria in Victorian England, they are designed to maintain the elegance of a dress boot, while sporting the alternative style of no laces, straps, or buckles. Commonly made without any adornment, the clean look makes them versatile. They are easily paired with jeans and can add a unique flare to your suit attire.

opera pumps

Pictured Above: L.B. Evans Duke Opera

7. Formal Pumps (Opera Pumps)

Formal Pumps, also known as Opera Pumps, have been the black-tie event shoe choice since the 1800s.

Much like the Loafer, they are laceless slip-ons, which offer comfort and convenience. However, the Pumps are reserved for the most formal of events.

Typically made with shiny black leather, and decorated only with a grosgrain ribbon on the cap, the simplistic, sleek design is intended to be paired with tuxedos.

Construction Marks of A Quality Dress Shoe

The many styles of dress shoes does not end there. The construction of the shoes add yet another layer to your shoe choice. Designed with six principal constructions, the difference can determine whether the shoe is more or less formal.


Typical of Oxfords, the plain toe is just that; plain. There is no adornment, and can be generally interchangeable between casual and formal


Sharing many features of the Oxford shoe, the Cap-toe shoe is also a versatile but formal shoe. Cap-toe meaning an extra layer of leather at the toe, these shoes add a little more uniqueness to the formal section of your wardrobe.

Unlike the Oxford, the Cap-toe shoe do not expose the tied laces, giving them a simple and sleek look fit for many occasions. The darker and sleeker the design, the more formal they become. The less dark, the more causal they become. A pair of brown Cap-toe shoes can even be paired with jeans, making them fit for more than just the office.

Also famous for over two hundred years, it is no wonder why they still are a vital part of the men’s wardrobe today. They feature a flare of style, while maintaining the simplicity and elegance, creating a perfect fit for all.

Wingtip Dress Shoes

These classic yet unique dress shoes reject the idea of plain, simple-faced shoes. To add a noticeable flare to your attire, these shoes are a popular choice.

Their name stems from embroidery on the cap-toe, which seem like wings stretching along the face of the shoe. Usually featuring brogue leather, they are the centerpiece of any formal attire. The laces maintain the classic appearance of your typical dress shoe, making them perfect to use for your semi-formal work attire, or with your tuxedo on special occasions.

Dating back to the 1920s, these formal shoes come in a variety of colors, and recently the two-toned wingtips are making a comeback in style. To add flare to your formal wear, the wingtips are the edgy but classic style for you.

Pictured Above: Peal & Co.® One-Piece Medallion Toes


Not very common among formal dress shoes, the medallion style is the punch-designed leather at the toe of the shoe. It is most commonly seen in “cowboy” boots, and not intended for formal attire.

Apron: also called the Moc Toe, the Apron gets its name from the appearance of an apron draped over the sides. An extra layer of leather is stitched around the sides of the shoe, and is commonly seen in Loafers, however it is also used in more formal shoe choices.


Essentially the Apron Toe, this construction adds an extra stitch down the tip of the toe in the middle, giving the name Split Toe.

Beautiful Brogues And All About Them

Brogueing, which means the decorative patterns on the dress shoes, is designed with 4 main styles. Much like the construction of the shoe, the brogue of the shoe can decide how formal the shoe is.


Also known as Half-Brogue, this style of brogueing is one of the most subtle forms. Maintaining a simple elegance, the semi-brogue is seen on many types of formal shoes. The decorative patterns are located on the cap toe, and along the seam.


Full Brogues are essentially Wingtips. The brogue begins at the toe, and thins out along the sides of the shoe, creating a wing-like affect. The Full Brogue is a bold choice, and is generally not paired with casual wear such as jeans.


Quarter Brogues are the most subtle of them all. The adornment is only located on the seam of the cap toe.

longwind brogue


A more casual choice, the Longwing Brogue mimics the Full Brogue, however extends the entirety of the shoe. Identifiable by the W-shape of the brogue, it is commonly used in Derby shoes, and not intended for highly formal events.