History of footwear: How dress shoes have changed over time. Sketch of a Victorian woman and man in evening dress clothes sitting on a pouffe hiding behind a giant fan.

History of footwear: How dress shoes have changed over time

No gentleman’s wardrobe is complete without a pair of dress shoes. Whether you prefer Oxfords, Derbys, brogues, monk shoes or loafers, finding the perfect dress shoe to go with your dinner jacket, suit, or chinos is a mark of a stylish gentleman and empowers him to express his unique fashion taste.

But where did dress shoes come from? In our brief history of footwear, we look at the origins of your favourite types of shoes and how they changed over time. 

Table of contents:

What is a dress shoe?

Dress shoes are any shoe suitable for smart-casual or formal events. They are the opposite of athletic shoes. You typically pair them with a dinner jacket, suit, or chinos. They can be anything from everyday work shoes to special occasion shoes. 

Dress shoes as status symbols

Ancient Egypt

Shoes have denoted status for centuries, as far as 1200 BC. Egyptian priests and pharaohs wore sandals with a piece of leather curved around the top of the foot rather than sandals made from hemp or papyrus like the commoners to signify their higher status. 

Imperial Rome

Roman upper-class citizens wore well-made sandals categorised by colour. Senators wore black, while emperors wore red. Commoners and enslaved people wore very basic sandals, and prisoners wore wooden shoes intentionally made to make them feel uncomfortable.

China

In China, the smaller, the better. Women wore dainty silk embroidered slippers to demonstrate their petite size and attractiveness.

Medieval Europe

An exaggerated, long, pointed-toe shoe fashion craze gripped the Middle Ages in Europe in the form of poulaines or crakows, originating in Poland. Given their impractical design, the shoes were a status symbol. The longer the point, the less likely you were to perform manual labour, thus the higher your status. 

There was also the chopine, a premature version of the platform shoe, the height of which denoted a person’s wealth and status in society. 

However, by 1463, English King Edward IV passed the Sumptuary Law, limiting the length of toes to 2 inches because he didn’t like the style. This law and changing fashion tastes led to more wide-toed and rounder shoes.

Sketch of medieval poulaines.

16th century Europe

It’s also worth noting the heeled shoe fashion trend of the 16th century. High heels were originally riding shoes worn by the Persian military. However, the shoe style caught on amongst the nobility when the Persian envoys visited the Spanish, Russian, and German courts in 1599. 

The impracticality of heeled shoes for anything other than gripping stirrups made them a status symbol of nobility and conveyed a leisurely lifestyle. In 1670, French King Louis XIV officially codified the heel’s status, declaring that only noblemen could wear them.

Sketch of 16th Century high heels

18th century Europe

It wasn’t until the Enlightenment in the 18th century that heeled shoes became associated with femininity. The symbol of leisure was considered unmanly in place of individualism, ideas of merit, hard work, and productivity. 

What was the first formal shoe invented

You could argue that these early status symbols were the first formal shoes. They were often worn by high society and at court, where men and women wore their finest attire. 

But if you want to know what the first formal shoe invented was, with our definition of the modern dress shoe, it would have to be the Oxfords, Balmoral boots, Chelsea boots and Derby shoes, which have an intertwining history.

Oxford shoes

Before Oxford shoes, the only “dress shoe” option was a high-topped shoe fastened with buttons or knee-high military riding boots. In the first half of the 19th century, students used to trim their tall boots into medium-high boots for increased comfort, calling them Oxoniana. The shoe still had the button fastening on the side rather than down the middle. 

Singular blue suede Oxford shoe on an orange background.

Alfred Capped Oxford in Indigo Suede

The term “Oxford shoe” first appeared around 1846 in writings by Joseph Sparkes Hall (famous for inventing the Chelsea boot in 1851). 

He wrote, “The Oxford shoe… is the best shoe for walking. They are tied at the front because they have three or four holes. They are nothing more than what are now called Oxford shoes”. – The New Monthly Magazine.

Chelsea boots

Chelsea boots came soon after. Although not originally a dress shoe, Chelsea boots gradually became a favoured alternative to Oxford and Derby shoes for occasion wear.

Originally, they were designed by Joseph Sparkes Hall in 1851 for Queen Victoria for hiking and riding and were mostly referred to as paddock boots. They were only referred to as Chelsea boots in the 50s and 60s and were made popular by fashionable celebrities such as The Beatles and Mary Quant. 

Godwin Chelsea Boot in Brown Museum Calf Leather

Balmoral boots

At a similar time, Prince Albert also commissioned Joseph Sparkes Hall to create him a comfortable pair of boots for walking around the newly acquired Balmoral castle, which was stylish enough to wear indoors to social gatherings. 

Balmoral boots had a closed-lacing system instead, drawing inspiration from the common button-down boot of this period. Although originally commissioned as walking boots, they quickly became popular as dress boots. 

You could also attribute the origin of the Balmoral shoe to the Oxford shoe. Of course, the Balmoral is just a boot version of the Oxford shoe in that they both have a closed lacing system. Americans often refer to Oxford shoes as Balmorals. 

Elkington Balmoral Boot in Dark Leaf Calf/Oceano Suede

Derby shoes

Just as Oxford shoes were a rebellion away from uncomfortable dress boots, Derby shoes were a rebellion against close-toe lacing. It is commonly thought that the legacy of the derby shoes originates with the 19th-century Prussian general Gebhard Leberecht von Blücher. 

Von Blücher commissioned the shoe design in 1814 to replace the standard military boot, which was impractical and uncomfortable. The blucher enabled the general to prepare his troops for battle much faster because it was designed with laces and a below-the-ankle construction, so they could easily pull their shoes on and off. Derby shoes are commonly called Bluchers in the United States, while the term Derby shoe didn’t appear until 1862.

Sketch of historical derby boots.

Simultaneously, the 14th Earl of Derby Edward Smith-Stanley, a larger man, struggled to get boots on his large feet, so he commissioned his boot maker, who developed an open-laced boot that accommodated his feet better than closed-laced boots. Thus, this may have been the origin of the derby boot.

Loafers

The loafer design originated alongside the change in men’s formal wear during the mid-19th century. Until then, men wore a dinner suit (or white tie) for dinner or a morning suit for the day. However, the rise of the lounge suit (the single-breasted business suit we know today) threw traditional dress code conventions into disarray.

With a single-breasted suit worn instead of multiple throughout the day, footwear became the key signifier of formality. To signal a change in formality, men would change out of dress shoes and into loafers in the evening for more comfort and convenience. The first loafers were designed in 1847 by Raymond Lewis Wildsmith of Wildsmith shoes for King George VI. 

Many styles of loafers followed, including the penny loafer, Aurland loafers, Belgium loafers, tassel loafers, and the famous Gucci horse-bit loafer. 

Black leather penny loafers on a suitcase on an orange background.

Toby II Penny Loafer in Black Deerskin

Chukka boots

Chukka boots appeared much later. A British soldier, Nathan Clark (whose father ran C & J Clarks, later Clarks), introduced the design to the masses after being deployed in Burma during the Second World War. He noticed officers wearing sand-coloured ankle-height shoes with no more than three eyelets commissioned by cobblers in Cairo. These boots were lighter, with better grip than the British Army’s standard-issued boots, and more suitable for the desert, hence their other common name, “Desert boots.”

Sand-coloured chukka boots sat on a suitcase on an orange background.

Jackie III R Chukka Boot in Leaf Suede

Brogues

Although one of today’s most popular dress shoes, brogues were originally field shoes. Now decorative perforations, broguing used to be a way for water to drain out of shoes while walking in the Scottish and Irish bogs. They first appeared in the 16th century for Irish and Scottish farmers and workers in rugged and wet terrain, including variations such as the Ghillie style with open-throat water drainage. 

During the 18th and 19th centuries, they made their way to England, became popular amongst the gentry, and evolved from functional work shoes to more refined, fashionable footwear options. 

By the 19th century, the brogue shoe had become a staple in men’s fashion, particularly among the upper classes. Considered a symbol of status and refinement, they were paired with formal attires like suits and morning suits. In the 20th century, the brogue transformed as shoemakers experimented with different styles and materials. The full brogue or “wingtip” emerged, featuring an extended cap toe with wing-like extensions. The semi-brogue was also developed, featuring a straight-edged toe cap and fewer extensive perforations. Although John Lobb claimed to have designed the first two-tone spectator shoes for cricket in 1868, they were more popular during the 1920s and 30s.

Black leather Oxford brogues on an orange background.

Ashburton Oxford Brogue in Black Calf Leather

Monk shoes

Monk shoes stand out in the narrative because they were developed by 17th-century European monks rather than shoe designers. Their design was to provide a more durable alternative to sandals while conducting manual labour. The design also featured a toe cap to provide additional protection. However, they take their inspiration from sandals featuring either one or two buckles instead of laces, making them easy to take on and off.

It wasn’t until the 19th century that shoe designer Edward Green reinvigorated them and made them popular as dress shoes. 

Double monk strap shoe in brown suede on an orange background.

Eddy Double Buckle Monk Shoe in Plough Suede

Essential formal footwear at Cheaney

Of course, in the 21st century, formal footwear has come a long way with the advent of rubber-soled shoes and innovative dying techniques to create luxurious colours and a plethora of leather types to choose from. There is now more choice than ever to pair with your formal and smart-casual attire. Where footwear used to be a status symbol, your type of footwear choice now signals your creativity and fashion sense. 

Complete your dress shoe wardrobe at Cheaney with our men’s and women’s dress shoe collections. Whether you need formal shoes for work or your next special occasion, find exceptional shoes steeped in history at Cheaney. 

Related blogs

Comments are closed here.