9 Major Types of Men's Dress Shoes - Explained with Pictures

type of dress shoes

“The only difference between everybody and nobody is all the shoes” as aptly put by Amor Towles author of a ‘Gentleman in Moscow’. They say that the most noticeable thing worn is on a man’s feet. There has been a lot said about shoes as they are a symbol of high fashion, a mans’ pecuniary status, asceticism, comfort and a whole, whole lot more. One architect of a nation, Mahatma Gandhi made his own to promote self-reliance.

One can wax long on this topic since there are many types of shoes such as Espadrilles, Runners, Boots, Safety Boots, Formal Shoes, Sneakers, etc. but our agenda is restricted to the type of dress shoes. We head there now.

Different Types of Dress Shoes

Since we will be discussing shoes, it is best to get a look at what we are referring to in the process.

Different Types of Dress Shoes

1. Oxford


The most traditional, the most classically handsome, the most practical, and the most versatile. It is peerless, goes with any dress color, and is the workhorse amongst shoes. Caring for them is not some complex, but key. They are capped so the shape remains intact and you don’t stub your toes accidentally. Where to wear them? They go with a tuxedo and jeans as well. Just get yourself a pair of black Oxfords, somehow. They rule. There exists a common saying, the suit was tailored to accompany the Oxford, a tribute to the Oxfords as shoes to wear with a suit

2. Derby


Another beautifully crafted shoe as the Oxford. The lacing makes the difference. The Derby has “closed lacing” which, in a nutshell, means, that unlike an Oxford, there is no seam and the front of the shoe. The freedom of wiggling your toes is more in a Derby. It sports a relaxed look.

3. Brogue


Brogue also refers to an Irish accent which we have little to do about here. We are talking about another iconic masterpiece which is immediately identifiable because of the decorative and distinctive designing called broguing. The ornamentation consists of heavy perforations and pinking. The shoe originated in Ireland and was a working man’s shoe. 

Then, they became very popular with women, so calling them male dress shoes may be a bit of a misnomer. Brogues were finally accepted as a shoe for social and business occasions. In 1920, they were well entrenched as a style statement especially in America, Fred Astaire, Gary Cooper, and Cary Grant were chief patrons.

Their general characteristics are:

  • low heels,
  • Broguing or perforations
  • Toe caps
  • Heel panels
  • Lace panels

There are many different types; Full brogues or Wingtips, two-tone full Oxford, Derby brogue, etc.

4. Monk Strap

Monk Strap

The Double Monk Strap shoe has carved a niche for itself. In versatility, it is second to none. It is suited for diverse circumstances and settings. Sharp, is what you will look, be it a business brainstormer or a night out with your woman.

The history is as the name tells. They are of European origin originally worn by monks.>

The monk shoe had its share of uncertainty for a while, considered too casual for professional wear and too formal for casual wear. Today, the perception has swung right around.

The prepondering difference of the monk shoe is the absence of laces. A twin strap with buckles secures the shoe. They are available in a range of mind-boggling color combos; various shades of brown, oxblood, burgundy and black. Leather is the primary material used but a suede variant is also at one’s disposal. Remember suede shoes can get blemished easily and absorb liquid easily.

A monk shoe except for the black ones can be worn with or without socks. They go beautifully with a suit.

5. Loafer


Before diving in, we have to establish the ground rules as to how this differs from a slip-on.

  • A loafer has no laces it is slipped into.
  • It is called strangely a “low shoe”. The shoe is not ankle-clinging and a little ankle expose is left on purpose.
  • The sole and the upper are separate.
  • The heels are low.
  • A distinct moccasin like construction adorns the upper vamp.
  • Loafers sometimes have an attribute in the form of a piece of leather across the vamp known as a saddle.

The precursor of the loafer is, without doubt, the moccasin with some differences.

  • The shoe is a composite whole including the sole.
  • A moccasin is a flat shoe meant for foot protection alone. It, therefore, does not feature a heel.
  • Moccasins rejoice in embroidery, beading or other ornamentation; loafers maintain a more somber presence.

The history of this shoe is a bit convoluted. That it developed first in England as a house shoe is one. Most historians agree that Nils Gregoriusson Tveranger, a Norwegian hybridized native American and local footwear to come up with the loafer.

Loafers are of many types; Penny loafers, the Wildsmith loafer, the Aurland loafer, the Tassel loafer, and so on.

6. Chukka


These casual wear ankle-high boots sprang into the limelight in 1940in the United Kingdom. They have morphed into present-day formal wear. Fabricated from calfskin or suede, Chukka boots feature toes that are rounded and thin soles of leather.

They are unbound by the diktats of fashion and are compliant as casual or formal wear, for formals. Of course, it may not be for The Oscar Ceremony, but for work.

7. Chelsea Boot

Chelsea Boot

Woah! A show stopper that can best be described as a “dress boot”. It has elastic panels on the sides and a finger loop at the back for ease of getting into them.

It has its origins in the Victorian era, roared back in the swinging sixties of London and does not appear to be in any hurry to leave anytime soon.

Chelsea boots afford superior comfort and are very aesthetic. They are hip and straightforward. They work best with fabric that falls easily such as flannels. Another stunning combination is with a blazer and jeans. Though classed as a dress shoe it has limitations. Semi-formal is a better description.

8. Dress Boots

Dress Boots

Having seen the light of the day in the Victorian era too, Dress Boots have ruled the roost as a style icon for quite a few years. This ankle boot, simplistic in design, almost minimalist, is a rage among those who aim to look natty. Jeans and dress boots present a fantastic combo as their innate versatility draws out the best in them. Their classic look is equally effective when teamed with slacks. They are all-weather wear. Crow as much as we like about their versatility, they don’t go with suits or a tux.

9. Formal Pumps

Formal Pumps

Also known as the Opera Shoes, their vintage extends all the way back to the 1800s as an accessory for black tie events. They are unlaced slip-ons much like loafers bestowing on the wearer comfort and convenience. Their slot is reserved for the most formal occasions, men's dress shoes, full stop, if you will.

The archetypal pair of Formal Pumps are always of black leather, highly shined. The trademark decoration is the grosgrain ribbon on the cap. The simplistic yet polished look is only for tux gatherings.

The Construction

The genre of dress shoe styles has more to it. Construction brings in another angle into play. It is the arbitrator of whether a shoe is formal or not. Sometimes the toe construction goes wrong and results in creating tight space inside the shoe. You can use toe separatorsto get rid of discomfort due to this tightness. 

1. Plain Toe

Plain Toe

Elegance is but the magnified outcome of simplicity. The best example is rendered by an Oxford, Derby or Brogue, no cap, no detailing which catapults them into the No.1 formal spot

2. Cap-toe


The cap toe means a supplementary layer stitched into the top. Simplicity and elegance are kept intact while throwing in a flare of style presenting a remarkably comfortable fit for all.

3. Wingtip


These clearly reject the ideas promoted by simplicity and minimalism. There are straight put pushy classic dress shoes. The embroidery on the cap toes which closely emulates wings is what gives them their unusual nomenclature-wingtips. They quintessentially are formal attire.

4. Semi-brogue


Going by the label Half Brogues, the entire form of styling is both subtle and distinctive. The decorative elements are restricted to the caps and along the seams

5. Whole Cut

Whole Cut

One single piece of leather goes into fashioning the uppercut. This is the hallmark of an ultimate shoe in that the craftsmanship puts the screws on the maker. The result is the zenith of elegance.

6. Full Brogue

Full Brogue

Being necessarily Wingtips, the broguing starts at the toes and spreads along the flanks thinning out. It is a choice for those bold at heart. Do not pair with jeans. The offset of styles is overbearing.

7. Medallion


Among formal dress shoes, a bit uncommon. The toe of the shoe is punch-marked as is common in cowboy boots. These shoes are not suited for formal wear.

8. Round Toe

Round Toe

Simply put, the upper is rounded giving rise to a toe neither square or pointed. Its schoolboy charm is captivating.

9. Split


A derivative of the Apron or Moc Toe. It is thus named as Apron because it looks akin to an apron draped over the sides. As is common in loafers, an extra layer of leather is added on the sides. It is, however, though a formal shoe option.

The Split is essentially an Apron toe with a tweak; an extra stitch going down in the middle of the toe. Therein the name, Split Toe.

10. Chisel Toe

Chisel Toe

This one belongs to the rarer species. The squarer toe has more bite. On an Oxford it would signal irreverent elegance, while sat a Chelsea boot would definitely scream mean bean.

11. Tassels


Ivy Leaguers really take a shine to this one. Our good ol’ pal, the Loafer too. Many find it an unneeded prop, the tassels so much so that to call it stuffy. Well, to each his own. A good dresser knows the deal. Give it a pop of color.

12. Kilties


A kiltie is a tongue of leather that is fringed fastened onto the shoe’s vamp. From Chukkas to whatever, kilties can de an add-on, but hang on, most probably it may be a disaster. Your iPhone may not exactly take to a bib.


1. What men’s dress shoes are in style?

Oxfords, Derbys, Chukkas are perennial favorites. Any shoes guide will point it out. My preference runs to the Monkstrap. But regardless, choose a style that you are comfortable in and can carry off. All the listed shoes above have merits. The demerits are for you to find. The style adage is if your shoes are not comfortable, how can you be.

2. What is toe cap shoes?

A cap toe involves an extra leather layer over the cap of the toe section. It imparts to the shoe a uniqueness. It is formal wear.

3. Are toe cap shoes in style?

Cap-toes are eternal in their appeal. They have gone through the hammer of time. Their allure is something that will not fade easily.

4. Are almond toe shoes in style?

It is the most popular toe shape although much unpublicized. It is not square or rounded or pointed. The cap is well, like the name says, shaped like an almond. It renders a softer, more tapered point to its toe.

5. Can I wear protective accessories with formal shoes? 

Yes, you can wear arch support pads, compression socks, and toe separators if needed. But, make sure that you're not using vibrant colors as this will not complement formal shoes. 

Squaring it up

Shoes say it all. That debate is a no-contester. Over the world, different countries have traditional wear which has little to do here. This guide featuring the type of dress shoes is as durable as Wester classical music, irrespective of global location. The mantra is to choose and choose wisely. Of course, they are a tad expensive. So while the Christmas discounts still last, do yourself a favor; buy a pair of these natty numbers.



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