Monk Strap Shoes Guide

In recent years, double monks have become quite popular and hence it’s about time for us to discuss the monk strap dress shoe, including its history, what to look for and how to and how not to wear it.

Monk Strap Shoes Video

As always, the guide is not complete without the video, so watch the video and read the guide for the full experience.

Superbly polished burgundy oxblood double monks by Butler

Superbly polished by butler – burgundy oxblood bespoke double monks by John Lobb St. James

History of Monk Strap Shoes

As with many clothing items, the exact origins of the monk strap are unclear. According to some, it was aptly named, after a monk from the Alps who created a special form of sandals in the 15th century. Legend has it that a gentleman visiting from England took note of the shoes and was given a pair to take home with him. When he got back to England, locals were so enamored with the shoe that it became popular almost immediately.

Lizard skin captoe double monk strap shoe in black with silver buckles

If we stick to the facts, we can see that the monk strap shoe appeared as a registered design for the first time in 1901. As such it is more likely that it had its origins sometime in the 150 years before then.

Today, monk strap shoes are an integral part of a classic gentleman’s shoe closet and double monks have even achieved a certain kind of mainstream appeal. In Mediterranean countries especially, men often wear partially or completely unbuckled double monks to underline their nonchalant look.

Types of Monkstrap Shoes — Single Monk, Double Monk & More

Traditionally, the single monk strap was the only shoe around until the double monk strap made an appearance. With the popularity of two buckled shoes, some designers have adopted unusual variations with 3 and more straps. Realistically, the 3 or more strapped shoes will likely not be anything more than a short-lived fashion that will disappear in a few years. If you want to invest in a sustainable wardrobe that can be worn 10 years from now without looking dated, then a single monk strap or a double monk strap is the way to go.

Gold buckles on a tan monk strap shoe

Gold buckles on a tan monk strap shoe

Single vs Double Monk Strap Construction

Defined by the single broad strap that closes across the instep and fastens using a saddle buckle on the outside, the only difference between a single and double monk strap is the number of straps used to fasten the shoe to the wearer’s foot.

Otherwise, the monk strap is a traditionally designed, low-fitting strapped shoe with an upper that’s made from three leather pieces. To give the wearer a more comfortable fit, the monk strap uses a wider tongue compared to other shoes to help secure it around the ankle. This is needed as there are no laces used and the only fastener is the strap. With that said, double monk straps offer an additional strap, which in theory allows for a better fit — especially for smaller or narrower feet — though in practice that seems questionable.

Classic vintage style monk strap shoe

Classic vintage style monk strap shoe

RTW vs. Bespoke Monks

Ready-to-wear shoes always have a few holes in the strap to make a proper adjustment, whereas most bespoke monk straps will only have one hole because they are perfectly fitted.

Double Monk Straps in dark brown with patina, navy chinos and burgundy and beige striped socks

Double Monk Straps in dark brown with patina, navy chinos and burgundy and beige striped socks

Monk Strap Buckles Come In All Shapes and Forms

Monk strap buckles come in manifold shapes, thicknesses and sizes. Classic options include square, rectangular, oval and octagonal or hexagonal. Most of them are made of brass and then either chrome, or palladium-plated, but certain bespoke buckles are sometimes made of sterling silver or even solid gold. When choosing a buckle color, bear in mind that it should ideally match the hardware of your belt buckle, cufflinks, tie bar , collar pin, bag or other metal colors, though in practice you may not always be able to abide by that rule — and that’s OK as long as the overall look works.

Carmina alligator double monk strap shoe

Carmina alligator double monk strap shoe

Strap Spacing  & Positioning

While a single monk strap can be positioned a bit further up or down on the shoe, a double monk strap can look hugely different depending on the spacing and angle of the straps. Generally, unsophisticated lasts feature narrow spacing and often parallel buckles, whereas a slightly off-set angle with wide spacing seems more elegant to the eye.

Monk strap buckle detail

Monk strap buckle detail

Of course, this is a matter of taste to a certain degree, yet well regarded shoemakers and shoe companies never align the buckles parallel and always have them slightly off-set.

Sometimes you can also find monk straps with extreme narrow or wide spacing and buckles that are placed very low or high on the side of the shoe. As with many things in classic menswear, it pays to avoid extremes such as these because balanced proportions yield a more elegant, timeless look.

Double monk strap with narrower spacing and almost parallel straps

Double monk strap with narrower spacing and almost parallel straps

General Construction

Apart from these considerations, the same measures should be taken when purchasing a pair of monk strap shoes as you would when buying a pair of goodyear-welted Oxfords or Derbies.

Crockett & Jones Ebury Spectator Double Monk in Navy

Crockett & Jones Ebury Spectator Double Monk in Navy

Leather Is The Best Material For Monks

Some fast-fashion brands and designers have begun using unusual manmade and synthetic materials. Others have adopted exotic skins from alligator and lizard for their shoes. In the end, leather is your best friend. If you are just starting out, plain calf leather is best, and if you got that covered a pair in dark suede may be in order. Of course, once you have the basics covered you can also experiment with exotic leathers and contrasting linen or tweed. A brown alligator single monk strap is a very classic yet unusual choice, especially in matte leather on a refined last. Stay clear from the boxy last, high-shine alligator shoes because they look cheap.

EG Monk strap variation

EG Monk strap variation

 Single Cutaway Monk Strap Shoe

Apart from the traditional monk strap, in recent years a much more angled, cutaway version has been popularized by companies like John Lobb Paris and Edward Green. Rather than pointing down towards the welt, the strap points back towards the heel. It is certainly a more unusual style and while they look interesting by themselves, they don’t seem to be as pleasing to the eye when combined with trousers. Of course, it’s a matter of taste.

John Lobb Chapel in black

John Lobb Chapel in black

Double Cutaway Monk Strap Shoe

In the same vein, the double cutaway monk strap shoe has two buckles facing backwards. Personally, I find it more appealing than the single cutaway monk but it’s not a shoe you need in your collection early on.

John Lobb Chapel in brown museum calf

John Lobb Chapel in brown museum calf

Bspoke Split Toe Single Monk Strap Shoe

Bspoke Split Toe Single Monk Strap Shoe

Other Monk Strap Shoes

St. Crispin’s is well-known for creating unusual styles and they have come up with an unusual strap model that is unlike traditional monk straps. If you have all the basics covered and you are thinking about the 43rd pair in your collection, this can be a good option.

Sometimes you also see double monks with straps on either side of the shoe.

Triple Monk Strap Boots from Septieme Largeur

Triple Monk Strap Boots from Septieme Largeur

Monk Strap Boots

Once you have acquired a chelsea boot, desert boot, balmoral boot,  jodhpur boot, and button boot, you may want to add something else to your collection. That’s when the monk strap boot comes into play. With the strap and buckle placed higher than on a shoe it can look quite elegant in brown, especially with a tweed suit. Of course you can also find double monk and triple monk boots, although you have to be cautious.

John Lobb Highgate Monk Strap Boots

John Lobb Highgate Monk Strap Boots

Triple Monk Strap Shoe - not recommended

Triple Monk Strap Shoe – not recommended

3 Strap Monks – Not recommended

More blades on a razor are inferior in quality to a single blade — it’s very similar with monk straps: less is more, which means anything above 2 straps is too fashionable and flashy, which is why we recommend to stay clear of those styles.

Barbera in a SB beige jacket with a grey pants and striped tie in blue paired with a single monk shoes

Barbera in a SB beige jacket with a grey pants and striped tie in blue paired with a single monk shoes by Sartorialist

How to Wear Monk Straps

The monk strap is an intermediate formal shoe that’s incredibly versatile. In fact, one could argue it is one of the most versatile dress shoes, as it pairs well with casual, business casual, and less formal business attire such as blazers, tweedsnavy and grey suits. It’s not suited for funerals or morning dress, and it should never be worn with black or white tie ensembles.

One of the best parts of the monk strap is that despite it being a very popular shoe, it is still rarely seen in comparison to the more iconic Oxford and Derby. Average dressers who buy off-the-rack from chain menswear stores will typically not be wearing monks and therefore the details of the buckle and strap become a rather noticeable part of any gentleman’s outfit. A well polished and unique pair of monk straps will certainly get noticed.

Because it is classic yet unusual, monk straps are popular amongst well-dressed men. For example Luciano Barbera has a very high taste level and you can see single brown monk straps on his feet regularly. At the same time, younger chaps like Fabio Attanasio wear them as well.

Use A Shoehorn

Even more than with regular lace up shoes, it is essential to use a shoehorn when putting on monk straps.Even if you unbuckle all four buckles, it can be quite tight to get into the shoe and you definitely want to avoid damaging the heel cap of your shoe. If you prefer to stand when you put on shoes, get a long shoehorn — if you sit get this one and when you are on the road, the travel shoehorn is best.

Navy Suede Double Monk Strap shoes

Navy Suede Double Monk Strap shoes

Monk Strap DO’s

  1. If it’s your first pair, stick with a shade of brown since it’s quite versatile.
  2. Consider black only if you wear a lot of charcoal and grey suits. Otherwise consider oxblood or burgundy.
  3. Once you have the basics covered you can look into lighter shades of brown and suede.
  4. On a double monk, leave one strap unbuckled if you want to add some sprezzatura to your outfit. This is similar to unbuttoning one button on your jacket sleeve or leaving your shirt cuff undone. It’s a very popular trend and is prominently seen at Pitti Uomo.
  5. Pair them with striped, over-the-calf socks to add a subtle pop of color to your outfit.
  6. Reddish Brown Captoe Double Monks

    Reddish Brown Captoe Double Monks

DON’Ts – How Not to Wear Them

  1. Don’t wear monk straps with formal attire such as a tuxedo, morning coat or tail coat. They should also not be worn with a Stresemann or stroller coat because they are not formal enough.
  2. Monk straps work very well with casual wear including denim. However, they shouldn’t be paired with shorts or athletic apparel.
  3. Be picky when buying monk straps. Just as you would with other shoes, choose quality over quantity. Avoid budget brands, sales, and inferior materials or craftsmanship. A good pair of monk straps should last a very long time.
  4. Use a shoehorn & don’t slip them on. Although you may be tempted just to slip them on like a loafer – and the buckle may be stiff at first – it is always best to buckle and unbuckle your shoes the same as you would lace and untie your oxfords. This will increase the longevity of the shoe.
  5. Try to avoid overly big, shiny buckles as they will scratch easily and look worn after a short while. Consider smaller or larger brushed buckles and opt for brass if you will be wearing them with both gold and silver jewelry such as your watch, belt buckle, and cufflinks. If you can, try to match the buckle to your jewelry. Nothing will look more out of place then a gold buckle on your shoes and a silver buckled belt.
  6. When you wear a single monk strap, don’t leave it unbuckled as you might with a double monk strap. This is akin to wearing oxfords with your shoelaces untied.
Beautiful Monk Straps by The Dandy Project

Beautiful Monk Straps by The Dandy Project

What Monk Strap Shoes To Buy?

Just as with Oxfords there are hundreds of quality makers of monk strap shoes with various details and lasts. We cannot comprehensively list all of them although you can find plenty of monk strap inspiration here with this guide.


Shoepassion No. 591 – The Budget Double Monk Strap

Relatively well constructed for the price. There were some  quality issues (you get what you pay for), but overall it was a well-made shoe that provided immense value. Shoepassion has consistently improved their shoes over the years, so please take a look at the in-depth double monk review.

Crockett Jones Chadwick 2 – the Medium Budget Monk Strap

As with all leathers from the handgrade selection of Crockett & Jones, the Chadwick 2 has a nice hand-burnished patina and a wingtip with broguing, which is rather unusual for a monk strap shoe.

Crockett & Jones Chadwick 2 Monk Strap with silver buckle, blue linen pants and blue and navy striped socks

Crockett & Jones Chadwick 2 Monk Strap with silver buckle, blue linen pants and blue and navy striped socks

Bespoke – For High Budget

 If money is of no concern to you, getting a bespoke monk strap shoe is certainly your best bet, because no off-the-rack shoe will be able to provide you with the same level of fit. Even though you can adjust the strap on an RTW shoe, it is less flexible than a lace up shoe and hence it is more difficult to achieve a great fit off the rack. Needless to say the options for customization and details are endless.

Beautiful patina and custom medallion and buckle on a bespoke monk strap shoe by Ugolini

Beautiful patina and custom medallion and buckle on a bespoke monk strap shoe by Ugolini


Monk strap shoes are versatile, dashing and show a certain level of flair and panache that other dress shoes fail to offer. They are a shoe worthy of any gentleman’s collection and one we heartily recommend. Do you prefer the single or the double monk? How many pairs do you own?

This guide was written by Sven Raphael Schneider & J.A. Shapira

Monk Strap Shoes & Double Monks Guide
Article Name
Monk Strap Shoes & Double Monks Guide
Everything you need to know about Monk Strap Shoes incl. Double Monks, history, how to buy them, how to wear them. DO's & DON'Ts + style advice.
Gentleman's Gazette
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10 replies
  1. Dr. Mobeen Javaid Farooqui says:

    Hello, whe it comes to Monk strap, I think John Lobb’s RTW are not a bad choice. I have a biege / brown pair with almost parallel straps and mate brass buckles which is very versatile in summer with beige , kahakis and light olive troussers/suits. The only problem is that even after nearly 12 years of use, I still find them quite stiff. However, they look just great and worth every penny.

  2. Ian says:

    Great article. Monk shoes are my favourite and I have been wearing them for 20 years – with suits, with sport’s coats and with denim paired with a blazer. I normally have 3 pairs: black leather, brown leather and brown suede. I always “match the metal” to watch and cuff links and think they are the most versatile of all dress shoes. One can be casual or formal; staid or dashing – but never conventional. It is a style adored by Edward VIII and suits that 30s style. Personally, I adore them and pair them with single button coats. The double buckle, though, I leave to the under 30s. It seems to suit a shorter and narrower trouser. However, if you have the confidence, a monk shoe is a joy. My favourite is brown suede with chinos and a sock colour to match my shirt. Enjoy!

  3. Camaro Blackstar says:

    Never seen these shoes before. Could possibly buy a single strap but the double one looks horrible (the boot seems OK (but not with three straps !). These shoes may have been the inspiration for those cheap velcro fastening trainers you see in cheap sports shops ? LOL

Trackbacks & Pingbacks

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