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History of the Single Monk Shoe

Monks in the Field

Dating all the way back to 15th century Europe, the single monk shoe has gone from being a work shoe to something that represents class, sophistication, and ease. In the 15th century, monks devoted their entire lives to worship and manual labor. Some of the daily tasks they performed were reaping, sowing, and planting crops for their local village. Originally the monks wore a double strap sandal when performing their duties. Unfortunately, this did not work well when having to traverse mountains or hills, so they came up with another option…the single monk shoe. The single strap allowed the monks to go about their daily activities with ease as they did not have to worry about the weather or the terrain.

Custom Made Men's Goodyear Welt Single Monk in Italian Calf Leather with a Fire Hand Patina 
Hand Patina Single Monks from Robert August

Over time the single monk shoe was adopted by the general public as an alternative shoe style. As a nod to the original and durable shoe the monks wore you will find them with a cap-toe. They also have been upgraded to include plain-toes, brogues, and also boots.

When it comes to the construction of the shoe, the look is somewhere between an oxford and a loafer. It slips onto the foot but includes a tongue like a closed shoe. Instead of laces, there is a single buckle. Buckles are considered formal due to the clean lines, which is why this shoe is very popular.

The straps of the shoe are usually at an angle and are never parallel, which gives it a sophisticated and uncrowded look. Monk shoes today have buckles that point towards the sole of the shoe, whereas before, they went through a trend of pointing towards the heel.

The strap buckle comes in multiple shapes, thicknesses, and sizes. Classic options include square, rectangular, oval, and even octagonal or hexagonal. The majority of them are made of brass and then either chrome or palladium plated. If you get a pair of bespoke monks their buckles will either be sterling silver or solid gold. When choosing the right buckle, you want to make sure that it will match the buckle of your belt or any other metal colors that you plan on wearing.

The leather of the shoe is today usually made with coarse full-grain calfskin. People love this letter because it tends to develop a lovely patina look over time. At the moment though Suede Monks are becoming very popular and are really a great casual choice that will give anyone’s outfit a bit of spice.

So now that you know about the history and making of the shoe, let’s discuss the best way to style them.


If you are planning a casual day out, let’s say shopping with friends and maybe a light lunch, this is the perfect shoe to wear. They can be paired with a dark pair of jeans and a nice shirt, or if it is a little cool outside, you could throw in a sweater. When going casual there are usually two things you want to pay attention to…going sockless and having a break between the pants and the shoe.

Business Casual

If you plan on wearing these shoes to work, you’re going to want to make sure that business casual is allowed. The best way to pair them for this particular look is with a pair of slacks or chinos, and a casual button-down shirt. The key here is to make sure your trousers cover the tops of your shoes. This allows them to be viewed as more of a business shoe.

With a Suit

When paired with a suit, the result is looking quite dapper. You want to make sure to only wear them to semi-formal events. If your suit is black, then choosing a pair of black monks will be the most suitable option. Keep in mind though, that for a semi-formal event it is always good to choose brighter colors so that you don’t look overly formal. Your best option would be a casual blazer with sleek trousers. Your dress shirt is where you can have the most fun and choose something with a pop of color. If you want to appear laid back, choosing a shirt with a pattern is best.

Now that you know how to style the single monk shoe, let’s look at some simple do’s and don’ts that you should abide by.


  • When purchasing your first pair, stick with a shade of brown since that is the most versatile.
  • If you wear a lot of charcoal or grey, then you will want to consider getting your monks in black or even oxblood or burgundy.
  • Once you have your basic pair you can then look into purchasing lighter colors like brown and suede.
  • If you want to add a slight pop of color to your outfits you can pair them with over the calf socks that are patterned.


  • Wear monks with formal attire.
  • They work well with denim, but you must never wear them with shorts or athletic apparel.
  • Focus on the price. You want quality of quantity, therefore if you purchase a pair of monks from a reputable shoemaker, they will last you forever.
  • Don’t slip them on. Be sure to use a shoehorn. If you want to increase the longevity of your shoe you will want to make sure that you are unbuckling them and putting them on properly.
  • Wear a silver buckle if you are wearing gold anywhere else. You want your outfit to look cohesive.

Here at Robert August, you can use our 360-degree design studio to create your own custom-designed men’s single monk shoe. Once ordered, your shoes will be handcrafted in our workshop here in Almansa, Spain. We are proud to say that our history in artisan shoemaking dates all the way back to the early 18th century. We only use the finest leathers to craft your shoes from tanneries in Italy, Germany, and Spain. Our sartorial fabrics are obtained from prestigious mills in Italy, France and Belgium.


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