Types of Dress Shoes – Explained

The 5 Most Common Types Of Dress Shoes Explained

Today’s post will introduce and explains the most common types of men’s dress shoes.

Whether you have been working for a while and am looking for more fa-ducation (fashion + education) or just stepping into the society and looking for some info to help get started, this article might just have what you are looking for.

Related Post: 6 Easy Ways to Look Sharper In Office

Before getting into it, it is important to understand that not all dress shoes styles are suitable for all occasions – multipurpose.

Depending on the event you’re attending, some dress shoes are more suitable than others while some allows dressing up and dressing down based on the way you match them with your apparels.

Now that we’ve got that out of the way, lets dive right into it.


The Oxford Dress Shoe


One of the most popular dress shoe style among gentlemen…

The Oxford (also known as Balmorals) is the most basic and classic style of the dress shoes. They have an elegant, dressy and formal appeal that is a great starting point when you start exploring dress shoes for your office wear.

They can come in slight variations in terms of detailing, stitching, material and color. Typically the sleeker the design the more formal the shoe.

Like most dress shoes, the oxford shoes typically come in black, brown, burgundy,  cordovan (a rich shade of burgundy), chestnut and even white.

Because of its minimalist appeal and ability to dress up and down accordingly, Oxfords are great all-round dress shoes for formal and semi-formal occasion. For formal events and function, opt for black oxfords made of more polished and shiny leather sleek cutting and details.

The Derby Shoe


Originally intended as a hunting boot – The derby shoe (also known as the Blucher or Gibson shoe) is often miscategorized as the oxfords as there are very similarly shaped with only slight difference in the facing placement.

The derby shoe has the facing stitched on top of the vamp whereas the oxford’s sewn on under the vamp. This open lacing makes the derby shoes’ fit wider than an oxford, hence making the derby shoe a less formal and more comfortable option.

Derby shoes come in a variety of leather and different types of shoe-tip – brogue and non-brogue, cap-toed, wing tipped. Compared to the Oxford style, they are more suitable for smart-casual style like with jeans, sweat coat, sports coat.

Avoid matching these with suits.

The Loafer


The loafer is most recognizable by its slip-on style and lack of buckle or laces.

It resembles a moccasin but have a wider heel, hence was intended as a casual shoe until businessmen and lawyers in the US started wearing them with suits and office attire.

Loafers featuring decoration strap like a saddle, a strap with a slit, tassels or metal plate/ buckle used to be trendy. However, more classy designs like the Venetian, where simply has the vamp exposed across the front of the shoe with no decoration have fast picked up pace and am now the only type of loafers we would recommend.

As they slip on and off easily, the loafers are ideal for traveling business man (i.e when going through security and when on the plane). They are comfortable and versatile, and can be dress-up or down according to the outfit and occasion. The simpler, darker and sleeker the design, the more formal it is.

Image Credit: buyon

The Tassel loafer is a popular type of loafer to go sockless (or invisible, below-the-ankle socks) on a Friday dress down or on occasions where you don’t want to be formal yet does not want to be too casual. Although they are accepted as dress shoes in some circles, we would recommend wearing it on a semi-formal casual occasion or setting.

The Tassel loafer is our favorite shoe to wear on a wedding matrimonial, wedding lunch or dinner. Goes really well with a blazer or informal suits.

>> Shop Loafers Here

Formal Pumps

Image credit: theblacktieblog

The formal pump (also known as Opera pump) is the formal version of loafer made from shiny black patent leather. There is typical is a grosgrain ribbon decoration across the cap of the shoe.

The formal pumps are a good alternative to the formal oxfords which is also suited to go with formal black and white dress outfit.

The Dress Boot

Image credit: Aliexpress

Dress boots are sleek, ankle-length boots with a slight heel that look fantastic with both casual and formal clothes. For formal occasions, go with dark colored leather (i.e. black, dark brown) and more casual occasions, lighter brown leather or even tan leather are acceptable,

The dress boot come in a wide variety of styles – such as the monk stap, brougai, wing tip and cap toed – and are commonly matched with a fitting pair of dark-colored jeans or a pair of dress trousers with casual suit/ blazer.

The Dress boots is an ideal option for cold countries and seasons. They also bring some ruggedness to your usual dress footwear.

The Monk Strap

Image credit: urbanmaterialmen

The Monk strap is a style between the oxford and derby in terms of formality.

The distinctive look of the monk strap is its wide strap that is fastened across the front of the shoe with either a single or double (sometimes even triple) buckle closure.

Its uniqueness is perfect for those who seek attention. Just be sure to take note when it comes to matching, make sure that the color of the clasp matches your belt buckle (i.e. silver, brass, or gold).

As the design is geared towards the bulky side of dress shoes, we will typically match these with a ‘heavier’ top like office shirt with vest/ blazer/ suits or with ‘thicker’ bottoms like a pair of jeans. This helps take the weight away from the shoe and distribute that weight across the whole body length.

The Chelsea Boot

Image credit: Ask Men

The Chelsea boot features elastic siding which allows ease of wearing and taking off, which make them a practical alternative to the rigid traditional boots.

These boots are ankle length with rounded toes and low heels.

With the vamp and the quarters joined by elastic, the Chelsea boot has an incredibly clean look with the vamp and quarters each being made from a single piece of leather. This keep stitching to a minimum and help maintained the boot’s sleek and minimalist look.

As with other boots, match polished leather for formal (or even casual occasion), and wear the suede pair for casual or semi-formal events.

Asos.com has a good collection of Chelsea Boots.

The Chukka Boot


Chukkas are ankle-length boots with eyelets on the sides for a lace-up closure. Unlike regular boots, chukkas will not disrupt your pants’ shape.

Traditionally made of soft suede fabric, Chukkas have a rounded toe front and open lacing (similar to the derby). Chukkas are similar with the desert boots in terms of the shape are different in a few ways. The Chukka is less casual than a dessert boots and features a rubber sole instead of the traditional leather.

They are really comfortable (if you choose the better brands) and can be a good addition to your collection of shoes as they can add many variations to your dressing style and look.

White Buck Dress Shoe

Image credit: Reddit

The White bucks are Oxfords made of white buckskin – usually from deer, horse, elk or moose.

They are not really white in color and are less common in modern functions or night events. They are more applicable for day events or functions like the Memorial Day.


Any shoe can have brogueing.

Brogue simply refers to the decorative perforations of patterns on the dress shoes. Most commonly seen on derby, oxford, and the monk strap shoes, they come in four different toe cap styles: full brogue, longwing brogue, semi-brogue, and quarter brogue.

Image credit: effortlessgent

Full Brogues (aka Wingtips)

Full brogues take the shape of a wing-shaped cap, with the brogued cap coming to a peak opposite the toe, while its sides extend to the sides of the shoe.

Longwing Brogues

The shoe’s brogued cap takes on the same W shape and extends both sides down each side of the shoe all the way to its center seam in the back. It’s most commonly seen on the derby shoe.

Semi-Brogues (aka half brogues)

Semi-brogues feature broguing along the seam of the cap toe as well as some decorative broguing on the center of the cap toe.

Quarter Brogues

The quarter brogue features decorative broguing along the seam of the cap toe with no decoration on the center of the cap toe. This is the most reserved of all the above-mentioned styles.

Fun fact: the perforations of brogue were originally designed to allow water out of shoes when crossing wet terrain.

>> Shop Brogue Shoes Here (Free International Shipping)



Now let’s get down to the details, Toe style.

The choice of toe style can show a bit of your fashion taste and personal style.

Note: There is one golden rule regardless of your choice of Toe Style – ROUNDED AND NEVER SQUARED.

Image Credit: Ties.com

Plain Toe

Clean, minimalist and simplest design with no design or stitch on the vamp.

Cap Toe

Cap toes are essentially decorated oxfords where – simply put – features a horizontally stitched line that divides the vamp of a shoe at the toe. There is in fact an additional layer or band of leather over the toe.

Cap toes have a larger leather band than the oxford with contrast stitching over the toe gives them an extra edge. Depending on the style of the shoe and formality of the event/ function, the cap toed dress shoes can be worn with suits or even jeans.

Split/Apron Toe

The split toe (also known as apron toe) is more common on casual shoes as it features a seam that begins in the middle of the shoe, around the toe, and ending at the middle of the shoe (on the other side).


Medallion is a plain toe style and with essence of brogue decoration at the toe portion.


The Wingtip shoes are Derby shoes decorated with brogue leather.

Wingtip style, as the name implies, refers to the shape of the cap toe that looks like wings spread across the front of the shoe. They are mostly produced in solid color although two-toned versions used to gained popularity sometimes back.

Side note: This toe style is our personal favorite as we have broad feet yet enjoys wearing brown leather dress shoes.

Final words

Owning a pair of dress shoes is an absolute essential of every man’s wardrobe. Ideally, you should have a few pairs for multiple occasions and functions. A well-crafted pair of dress shoe should be timeless and expresses your style and fashion personality.

Related Post: Where To Buy Funky Socks

When shopping for dress shoes, you must first like the aesthetic look of it before anything else (i.e. pricing, fit, feel etc.).

As with any tips given at MWS, always try them on before buying.

When you try them on look for these few things: 

Sleekness – Whether it looks sleek and nice as an overall, or does it make you look like ‘Big Foot’ or Ronald McDonald.


Sole on the shoe – whether it’s slippery or do they have nice sole with decent friction (the last thing you want is to dress smartly but slipping all over like a penguin on slippery ice).

Workmanship – The sole should be stitched onto the shoe instead of glued on.

dress-shoe-sole-stitchingImage credit: loake uk

Do also bear in mind that the quality of the leather also plays a big part. Always opt for real leather and try them on to ensure they fit comfortably.

If you are just starting to build your wardrobe, go for more simple styles and start experimenting from there. Once you start building your collection, one pair will hardly seem like enough (you might be able to understand why girls just can’t own enough pairs of heels).

Now for out there and pick one you like and dress for success.

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