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

From your classic 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 dress shoes are not only to fit different tastes, but also other occasions.

oxford and derby dress shoes

Pictured Above: Johnston & Murphy Conard Cap Toe Oxford

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

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 intelligent 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 design (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 almost a one-type-fits most occasions. By simply changing the color, the Oxford shoe can be worn for different events. Black for more formal occasions, and brown for lesser occasions.

Although the Oxford is exceptionally 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.

2. Loafer Dress Shoes

loafer dress shoe for men

Pictured Above: Gucci Donnie Bit Loafer

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

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

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

Related: Types of Loafers

Sometimes still referred to as Penny Loafers, these timeless shoes stem from 1800s Scandinavia and are famous worldwide. Its quick, comfortable, yet formal design makes 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 leave your front door.

3. Monks

double monk dress shoes

Pictured Above: Calibrate ‘Cusano’ Double Monk Shoe

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

As the name suggests, monk strap shoes were initially the shoe choice of European monks who favored buckle’s secure yet quick function.

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 workplace often comes 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.

Related: Types of Monk Shoes

single monk vs double monk

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

4. Chukka Boots

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

Initially 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. They are generally not paired for tuxedo-worthy events; however, these boots are the perfect addition for a semi-formal gathering or a workday at the office.

5. Dress Boots

dress-boots

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

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 looking sharp while maintaining a minimalistic style.

Dress boots are incredibly versatile and can be 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.

6. Chelsea Boots

Pictured Above: Cole Haan Lenox Hill Chelsea Boot

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

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

Initially 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 flair to your suit attire.

7. Formal Pumps (Opera Pumps)

opera pumps

Pictured Above: L.B. Evans Duke Opera

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-on, which offers 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 construction of the shoes adds yet another layer to your shoe choice. Designed with six principal constructions, the difference can determine whether the shoe is more or less formal.

Plain

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

Cap-toe

Sharing many features of the Oxford shoe, the Cap-toe shoe is also versatile but formal. Cap-toe means 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 does not expose the tied laces, giving them a simple and sleek look fit for many occasions. The darker and more elegant 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 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. Instead, to add a noticeable flair to your attire, these shoes are a popular choice.

Their name stems from embroidery on the cap-toe, which seems 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 various colors, and recently the two-toned wingtips are making a comeback in style. To add flair to your formal wear, the wingtips are an edgy but classic style for you.

Medallion

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 shoe’s toe. It is most commonly seen in “cowboy” boots and is 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.

Split

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 four main styles. Much like the shoe’s construction, the brogue of the shoe can decide how formal the shoe is.

Semi

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

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

Quarter

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

Longwing

longwind brogue

A more casual choice, the Longwing Brogue mimics the Full Brogue. However, it 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.

About Adam

As the lead editor of Tools of Men, Adam is an expert in all things men's grooming and style. When you don't find him reading up on the latest style trends, he likes to go jogging, attempt to distinguish the differences between IPAs, and play sports with his kids.

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