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History Of Monk Strap Shoes | Timeless Elegance For The Modern Man

Carlos Santos Monks for The Noble Shoe IG

Discovering The Beautiful History Of Monk Strap Shoes

Few shoes impacted my life as much as the Double Monk Strap. In fact, they are the inspiration behind my foray into shoemaking with The Noble Shoe. While brainstorming for a new article I though “Why not write an article about the History of Monk Strap Shoes?

Researching the rich history behind certain styles or leathers is a rabbit hole. There is so much, or so little information that makes it such an engrossing experience. It allows you to fully understand the reasoning behind their creation but also find the kind of personal style you seek.

So with Autumn in full swing may I suggest you grab a cup of warm coffee and join me as we dive deep into the History of Monk Strap Shoes!

Stepping Through Time

What makes Monk Straps unique is not just their looks but also their origin. Most of the shoes today have roots in royalty or the military. Chukka Boots and Derbies make fine examples of this. However, you don’t have to be the world’s greatest detective (Batman) to guess where Monk Straps come from.

Tracing the exact date of this style of shoe is impossible. It is safer to say however that it made its appearance somewhere around the Middle Ages (1000 – 1500 AD). There is an urban legend circulating around the web that an English Gentleman visited a monastery in the Swiss Alps and brought the design back with him to London. Unfortunately, nobody can provide a reference for this claim so it could just be local folklore.

monks painting pinterest
Painting of a Monk’s sandals | Picture from Pinterest

Nonetheless the whole idea behind Monk Strap Shoes is very simple. Back in the Middle Ages, monks lived a very simple life. Most of them spent their entire lives in the Monastery grounds and required special permission by their Abbot to exit.

In addition to that they lived a very simple, poor life of solitude that included very little apparel. Monks used simple sandals which were not great for efficiency during manual labor. It just did not provide sufficient protection when working in the field or rougher terrains. Therefore the need for a practical, durable solution led the the creation of the monk shoe.

What they did was essentially make a closed version of their sandals with a strap. You could say that it was literally just a leather sock with a buckle. Very interestingly, they also had double buckle versions back then. Finding actual pictures can be rather challenging actually. This replica here should give you a good general understanding.

History of Monk Strap Shoes - Vintage Buckle Shoes
A replica of early Medieval Shoes | Available on Etsy

I love the deep duality and contrast of Monk Strap Shoes. Roots in a simple life and made out of a few pieces of leather and a strap, yet one of the most striking shoe designs out there today. A perfect companion to dress up jeans or stay formal with a suit, a good pair of Monk Straps is one of the most flexible shoes out there today.

Characteristics Of Monk Straps

You could say Monk Straps are a hybrid shoe. They have no lacing so in a way the resemble more of a slipper yet it feels and looks more like a Derby in a way. More often than not you will see it with a Cap-Toe on the front, but there are many variations out there.

The most distinctive feature is of course the buckle on the top. A piece of leather that usually runs across the instep to fasten the shoe and secure your foot. It is a very easy and convenient way to do it which shows why the monks of old opted for this. Nowadays, the most common Monk Straps have two buckles, whereas the single strap Monk is still elegant yet often underappreciated.

Of course, you can find shoes with 3 or more straps, boot versions with buckles or even sneakers and loafers. Outside of Septieme Largeur, I find it difficult to like any of them and I consider them short lived trends.

As far as details go, they certainly are more uncommon but you can find plain toes, medallions and brogues or even an apron toe.

Construction Details

Of course being a commercially popular shoe everybody makes Monk Strap Shoes these days. If you live in a nice warm country you can get a sleek, elegant and lightweight Blake shoe or for longevity and quality Goodyear Welted. No matter what you choose, avoid shoes with cemented construction as they will not last. You can read our very helpful article about the different Methods of Shoe Construction.

If we talk about a traditional Cap-Toe Monk Strap it consists of 3 pieces of leather stitched together. This is how it resembles the Derby in my opinion. Things can get really technical when someone speaks about the buckles.

The Single Monk Strap

Underrated, yet elegant and rather formal. The Single Monk Strap is less but more. In the business world at least. A very clean design with a single buckle that is a safe option for any type of everyday smart wear.

Carlos Santos Single Monk for the noble shoe
Carlos Santos Single Monks for The Noble Shoe | Available for 270$ on the Z401 last in 12 colors

The Noble Shoe will begin offering Single Monk Strap Shoes shortly through the Carlos Santos Patina Service. You can already do that by emailing me!

Crockett & Jones are some of the first to use this elegant design as one can see in their “Elite” catalog from 1924.

Origins of the Monk by Crockett & Jones
Origins of the Monk by Crockett & Jones

The Double Monk Strap

Single Monks were all the rage during the dawn of the previous century but over the past decades lost their place to their fancier brother. The Double Monks have an extra buckle and a bit more options when it comes to the spacing between them as well as the angle.

A superb, versatile shoe with a little more panache and flair. It is becoming increasingly popular although it was at its peak a few years ago.

History of monk strap shoes - Classic Carmina Double Monks
Classic Double Monk Straps by Carmina in Burgundy

You can find really nice Double Monks from every good brand. Which are those? Check the lists under under and over 400$! Or the Best of the Best if you are a high roller.

Triple Is..Not..Always Better?

Then we have triple buckle Monks (or more?) that are hit and miss. There is a lot to squeeze in a small area so they often look pretty ugly to me. An exception is a few really interesting models from Septieme Largeur or Saint Crispin’s.

Triple Strap Buckle Boots
Triple Strap Buckle Boots by Septieme Largeur in Pebble Grain Leather

It should not be your first choice, but a good way to explore your sartorial bounds if you have the basics covered.

Space Between The Straps

This is another interesting topic. Usually, the straps are at an angle and never really parallel to each other. It just looks better, or better say it looks horrible and crowded if they are. The buckles also point towards the sole whereas in another trend towards the heel. Think of them like the cutaway collars in shirts. I personally think they ugly, but everyone has their taste.

3dm triple strap
This looks aesthetically displeasing | By 3DM lifestyle

What About The Fastener Color?

When we buy a shoe we often overlook (or not) small details like the color of the laces or in this case the buckle itself.

If you are really interested in your appearance, have OCD or simply want to show you pay attention to detail, this is a great way to do it. Avoid very shiny ones and think of the rest of your accessories. Gold buckles with a silver belt? It will look out of place.

Trivia: RTW Monks have more than one hole in the fastener. Bespoke ones are supposed to have the perfect fit so have only 1!

Choice Of Leather

The sky is the limit here! I mean, you can go through our entire list of Types of Shoe Leather yourself. But hold your horses right there gentlemen. As with all things in life, you need to show intelligence and consideration.

If you have very few shoes or none my advice is to buy a Dark Brown pair of monks, or Burgundy/Oxblood since they are the most versatile. If however you have only grey suits and clothes consider a Black one.

For the actual leather the premier choice is of course full grain calfskin. It is clean, looks great and dressy and will develop a great patina over time. Suede Monks are becoming increasingly popular too and a chocolate colored one is a very good casual choice to spice up your outfits. Especially now that Autumn is really upon us.

history of monk strap shoes - crockett and jones suede
Lowndes Espresso Suede Double Monks by Crockett & Jones

Exotics are a very interesting area and while I am craving a blue alligator double monk pair, is out of reach for most people.

Designs Have Come A Long Way

A very short interruption, to discuss design. While you can see that even in 1924 the designs were classic and elegant, as products become commercially available there is going to be some experimentation. Apparently that happened during the 80’s and 90’s with the Monk Straps. Luckily, we are back on track and they are now more elegant than ever.

disgusting shoes by doctor martens
Atrocity by Dr. Martens in the 90’s

Here’s what happens when a pair of Crocs have sex with a Budapester shoe. Don’t buy any of these things please.

James Bond Approves

In a very interesting twist, I never noticed that James Bond often uses Monk Straps in his movies. Pierce Brosnan, Sean Connery and Daniel Craig have all worn them.

They are very fond of Church’s by the looks of it such as the Presley and Westbury Single Monks. Daniel Craig used a Double Buckle Boot instead in Spectre by Crockett & Jones called the Camberley.

Do’s & Don’ts of Monk Strap Shoes

While we approach the end of the article, I thought it would be a good idea to summarize what to do and not do.


  • Buy one for your wardrobe. It is a staple
  • Single or Double does not matter much. I prefer the looks of double
  • Start with a good versatile color. Brown, Burgundy or maybe Black
  • Buy only Goodyear Welted Shoes or at least Blake Stitched
  • Suede is a good option if you dress more casually
  • Use Shoe Trees and a Shoe Horn
  • Spice things up with colorful socks
  • Match the buckle color to your other accessories


  • Buy Cemented Shoes thinking you will save money. Quality over quantity
  • Leave a Single Monk unbuckled. That is not sprezzatura
  • Spend money on designs with parallel busy buckles.

Probably a whole more don’ts but I wanted to keep it simple!

How Do I Wear Them?

This section could be a whole separate article. It is impossible to know everyone’s style or cover every possible combination. So we will focus on the basics.

People say that Monk Straps sit between Oxfords and Derbies in terms of formality. In this increasingly casual world, it has never been more true. While you should never wear monks during Black Tie events or with evening attire, you can pretty much do anything else.

The Noble Shoe Monks

I think they look smashing with a pair of jeans especially in burgundy and dress them up quite a bit. Chinos in beige, khaki, navy and olive green are always a good match for most colors. The same applies to suits and separates. For a more formal look avoid excessive loud details like broguing and I feel monks compliment a blue suit exceptionally well.

Slap these bad boys under a flannel or patterned pair of pants and all eyes will be on you. The only other no-no for such shoes is wearing them with shorts, athleisure and all those unstable concoctions fashion comes up with lately.

A Shoe Worthy Of Your Wardrobe

Here we go gentlemen! We reached the end of yet another article. We had a nice quick History Lesson about Monk Strap Shoes. From the interesting origins, to the different variations and options I sure hope you learned something today. In fact, I feel like it would be great to continue these kind of articles in the future as well. Any suggestions of what you would like to read about? Leave a comment down below.

The Monk Strap is a gorgeous, dashing shoe with rich history. I was very uncertain in the beginning of my shoe collection career but now it is one of my favorites. Do not be afraid to be a little daring and you will surely look fantastic in it.

Until the next time, I am waiting for a large drop of items from MatchU Tailor and a whole lot of upcoming news and goods! If you are a new reader, consider Subscribing to Misiu Academy. Your support means a lot to me.

Thank you for reading,

Kostas Mandilaris,
Misiu Academy

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