Men’s Fashion – 7 Types Of Men’s Shoes And How To Dress Them

Men’s fashion is a big deal and no style can be complete without the right pair of shoes to top an outfit with. As a fashion designer who specialises in men’s fashion, knowing the various types of men’s shoes that there are and how to style these shoes, in case a client asks, is important for your business. 

Now, sit back and relax as we take you on a journey of all you need to know about men’s shoes.

“Wanna know if a man is well dressed? Look down.” – George Frazier

Types of Men’s Shoes​​

1. The Oxfords:

The Oxfords originated from Ireland and Scotland and first became popular in the 1800s among students of Oxford University. They are an elegant option which is strictly for work and formal occasions such as weddings, funerals, and job interviews.

Oxfords come in various styles and colours with black and brown being the most predominant colours of them all. Black Oxfords can be worn with any colour suit while brown can be worn with any colour suit but a black one. 

Oxfords are a staple for any man’s wardrobe and very versatile. With Oxfords, it is hard to go wrong with your dressing. Variations of Oxfords include:

  • The Cap Toe Oxford.
  • The Wingtip Oxford.
  • The Plain Toe Oxford.
  • The Whole Cut / One Piece Oxford.

2. The Derbys:

The Derbys is a close relative of the Oxfords but is different from it. They are the ultimate smart casual shoes and are perfect for work and play. They can sharpen up denim and loosen up a suit very easily.

Unlike the Oxfords, they are comfortable and practical for everyday use because of their shape which allows for a wider fit. Although Derbys are usually confused with Oxfords, there is a slight difference between them that fashion designers need to take note of.

The difference is at the top of the shoes. Oxfords are popularly known to have ‘close lacing’, i.e. the shoe’s facing is attached beneath the vamp, which provides a slim silhouette whereas Derbys have ‘open lacing’ i.e. the facing is attached on top of the vamp.

3. The Monks:

The Monks can easily be identified by the strap with buckles that replaces laces on the shoes. They are very similar in shape to Oxfords and are a great choice for formal outings or business travels. 

Monks got its name from the European monks as it was their go-to choice as they preferred the secure yet quick function of a buckle. Monks can have a single strap or double straps.

They can be worn to casual outings, also, and usually, steal the show when worn correctly. They often come with a cap-toe to provide an extra layer of protection. They are a bold choice of shoes for any man.

4. The Loafer:

The loafers are the go-to choice for any man that is short on time and wants something quick to slip on. They are designed for both formal and casual outings. The loafers come in various forms, from the sleek and formal loafers to the brightly coloured suede loafers, they are versatile and classy.

Loafers, often seen as dressier boat shoes, can be worn with or without socks of any colour and work well with chinos, jeans, or a suit. They feature a wide strap in front but are very comfortable and easy to wear.

5. Boat Shoes:

Boat shoes or espadrilles are a slip-on masterpiece. They studied and more versatile option than flip-flops and are comfortable for short distances and great for sandy shores like the beach. 

They are a great choice of shoes that should never be worn with socks and are perfect for almost any casual outing. They can be worn with denim, chinos, shorts, and beachwear. They are lightweight and very breathable and are the best looking casual shoes a man can find.

6. The Chukka Boot:

Chukkas are an ankle-length boot with few eyelets for laces. They have open-lacing like the Derbys with thin soles, rounded toes, and minimal stitching. They are made from soft suede or calfskin. 

Chukka boots are a perfect choice for smart casual and cannot be paired tuxedos or worn to very formal events. They can, however, be worn to sem-formal gatherings like an office event.

7. The Chelsea Boot:

Unlike Chukka boots, the Chelsea boots are a laceless ankle-length boot with rounded toes, low heels, and elastic at the ankle to make them easy to slip on. They have a slim silhouette and can be worn with a casual or smart-casual look.

Chelsea boots look amazing with jeans and can even be worn with a suit. They are a non-decorative and versatile choice for any man.


Contrary to popular belief, the brogue is not a type of shoe. I know, that got you, right? Brogueing refers to the decorative perforations made in any pattern on men’s dress shoes. Brogueing can be done on Oxfords, Derbys, and Monks and can determine how formal a shoe is.

Initially, brogueing was done on men’s shoes to let water out of the shoes when crossing wet terrain but nowadays they serve a solely decorative function. Brogueing comes in several ways:

  • Full or Wingtip Brogue: This is when the brogue of a shoe extends from the top of a shoe all along the sides of the shoes forming a wing-like effect. They are not to be worn casually.
  • Semi Brogue: This is when brogueing is seen on only half the shoe. They give shoes an elegant and formal look.
  • Quarter Brogue: This is the most subtle of them all as brogueing is seen only along the seam of the cap shoe with no decoration at the top of the cap.
  • Longwing Brogue: This is similar to full brogue but extends through the entirety of the shoe. It gives a more casual look and is usually seen on Derby shoes.

Types of Shoe Toes

As a fashion entrepreneur, it is important that you know the types of toes your shoes can have and how they affect the way your shoes are perceived. Types of shoe toes:

  • Plain Toe: As the name implies, plain toe shoes are plain shoes. They have no adornment whatsoever and can be used for both casual and formal outings.
  • Cap Toe: This type of shoe usually features an extra layer of leather at the top of the shoe. It has a horizontally stitched line that cuts across the vamp that caps the toe. They are a great choice for formal occasions.
  • Wingtip: They are a popular choice that adds a noticeable flair to any attire. Being anything far from plain toes, they are the centre of any formal dressing. The name ‘wingtip’ was derived from the brogueing design on it that seems to form wings that stretch across the face of the shoe.
  • Medallion: This style has a plain toe with hints of brogueing on the top of the cap. It is not intended for formal attire
  • Split toe: Also known as the apron toe, this toe features a seam that starts in the middle of the toe which runs around the shoe and ends in the middle of the heel. It is used commonly on casual shoes.

There you go dear fashion designers, the 101 of men’s shoes, and how to style them for your clients to ensure they never go wrong with dressing. 





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