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Men’s Dress Shoes 101:

Clothes make the man but without a foundation of good shoes, it’s like building a skyscraper on sand – shaky at best. Understanding some of the classics of men’s dress shoes allows men to make informed purchases that truly reflect their sartorial flair. After all, it’s important to know what the rules are before they can be broken.

MEN’S DRESS SHOES, Starting on the Right Foot

A good general rule of thumb is that a man’s shoe choice should be the inverse of how formal the event is. When donning a tuxedo, the accompanying shoes are quite plain (those are usually oxfords, by the way). They serve to support the look instead of distracting from it. Busier shoe styles – those with fancier elements – work better for casual wear.

With a limited budget, it’s best to start by buying the classics in traditional shades like black and brown. Once a man knows his style and taste, then it’s time to invest in a higher quality pair of shoes or even a bespoke pair for the ultimate in fit.


First worn in Scotland and Ireland, brogues reached their height of popularity around 100 years ago. Similar to oxfords, they are lace-up shoes with a low heel, and toe caps (at least) marked by decorative stitching. This decorative work is called pinking (when the lines look like they’ve been cut with alligator scissors) and perforations (dots that look like the leather’s been hole-punched).

Mens Brogue Ankle Boot
Mens Tan Brogue Ankle Boot by I MASCHI

Brogues come in several different styles. These shoes require several pieces of leather for construction. Quarter brogues have pinking only across the toe cap. Semi-brogues have pinking and perforations (sometimes called a medallion) across the toe cap. When there’s a W-shape stitched across the cap and perforations along the toe cap and seams of the leather, the style is called wing-tip. On a pair of long-wing shoes, the stitching that starts at the toe cap stretches all the way to the heel of the shoe, uninterrupted. It’s common to find some variation among these styles.

When constructed of leathers in contrasting colours, brogues may be called spectators. These shoes are also sometimes found as ankle boots. The variety of colours, construction materials, and broguing styles means that these shoes can be worn a number of places, from work to casual events but rarely to formal occasions. To successfully pull off a pair of brogues at a formal event, make sure they’re black and have minimal broguing.

Chelsea Boots

Mens Chelsea Boots

Chelsea boots have been worn since Victorian times and their origins are attributed to a shoemaker of Queen Victoria’s. They reached the height of their popularity during the mod era in 1960s Britain. Chelsea boots are pull-on ankle boots with elastic side panels; most have a loop at the top of the heel. Some Chelsea Boots are made with zippers. This men’s dress shoes style is often constructed from a single piece of leather, although that’s not a defining characteristic of the style. This is a versatile look for casual and work wear; Chelsea boots in black leather could be worn for a formal event, but much of that depends on the wearer’s personal style and verve. While traditional colours like black and brown are common, these shoes can be found in many other colours, too.


Mens custom Derby shoes

These shoes were often made of buckskin the mid-19th century and so were sometimes called bucks; they’re also known as Gibson shoes. Men wore them for outdoor sports like hunting, and they eventually made their way into being worn by town and city residents, too. While derbys look very similar to oxfords, what sets them apart is their open lacing. The eyelets of the laces are stitched onto the vamp. For this reason, derbys may feel like they offer a man a little more room in the shoe (basically, the laces are outside the shoe instead of inside the shoe). On a pair of derbys, tying the shoe won’t (nor is it expected to) bring the lacing panels completely together; it’s okay to see a space between them. Derbys come in a broad range of colours; light-coloured pairs are usually worn with summertime dress clothes, like linen and seersucker.


Genuine Crocodile Single Monkstrap Shoes
Genuine Crocodile Single Monkstrap Shoes

The oldest of the styles described here, these slip-on shoes originated in Europe during the Middle Ages with – you guessed it – monks. These men’s dress shoes feature clean lines and are considered to be fancier than loafers but just as comfortable. Monkstraps are secured by straps that cross over the bridge of the foot. Most pairs are made with one buckle or two. When worn in black, they could be worn to a formal occasion; in other colours, they’re great for work or casual events. Some monkstraps are made with broguing, which makes them more informal. Shoes like these are generally made with fewer pieces of leather, so these pieces must be as blemish-free as possible.


Custom engraved Oxfords
Custom engraved Oxfords

These are the epitome of classic men’s shoes and with good reason; if you buy only one pair of “good” shoes, these will take you everywhere. The lace-up oxford style developed during the mid-19th century and has changed very little since then. Today’s oxfords vary widely in terms of construction (e.g., leather, suede, canvas) which gives them great versatility.

The core element of the oxford style is that the eyelets are sewn under the vamp of the shoe; this is the part that covers the top and sides of the foot. When looking at a pair of oxfords, the piece of leather where the laces are will look pretty flat and level with the other pieces of leather it’s attached to. Tying the laces will bring the quarters (the parts that hold the laces) of the shoe together and give the shoe a streamlined and polished look. On a new pair of oxfords, it looks like a V under the laces. Once they’re broken in properly, that V disappears when the laces are tied; there’s just a line under the laces because the two pieces of leather meet evenly.

Oxford shoes often have 5 or 6 holes for laces, although this can vary by designer. The quarters (sides) of the shoes are curved at the ankle, allowing freedom of movement. The plainest style of oxford has only two parts, the quarter and the vamp.

Another common style of oxford is the cap toe. This style has an additional piece of leather that covers the toe box; a stitch runs across the top of the foot, near the toes. Oxfords like these are often sold in a wide variety of colours.

Less commonly seen are saddle oxfords. These shoes are made with leather in contrasting colours and are reminiscent of the saddle shoes that were popular in the 1950s, although the colour selections today are often more complementary and closer in shade than black and white (think tan and walnut, black and gray, or navy blue and light blue). Wholecut oxfords are even less common and usually more expensive. These shoes must be crafted from a single piece of flawless leather and are stitched only at the heel; seamless oxfords are almost always bespoke shoes and made without any seams.

At first glance, it may seem that men’s dress shoes, in general, have more similarities than differences. And that’s pretty much true, but the ability to discuss and describe the parts of a particular type of men’s shoe that are different and how they function allow men to buy the right style as a foundation piece in a wardrobe. Good shoes are an investment. While no one will spend a few hundred dollars on their first pair of oxfords, it’s important to learn how and when to wear them. That way, when a chap is ready to invest in custom men’s dress shoes for the ultimate in style and comfort, he can speak knowledgeably with a cobbler and get a bespoke pair he’ll wear with pride for years to come.