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Single Monk (Left) and Double Monk (Right)

Photos courtesy DJ Scammell

A Dress Shoe

By Douglas James Scammell

Published 1:56 PST, Wed December 17, 2025

FASHION FOR MEN

Another great dress shoe style that can really make your suit choice look that much sharper are to add the Monkstrap shoes. They are a dress shoe with no laces but designed with a buckle strap instead. There are 3 different styles: the Single Monkstrap, as well as the double monk strap and lastly the Cutaway monks.

1. Single Monk: The single monk has one broad strap that closes the shoe across the instep. It is typically kept closed by a saddle buckle made of metal. Some men’s designs feature wider tongues for more comfort. The single monk is a great choice for a subtle yet stylish look.

2. Double Monk: As you might have guessed, double monk shoes feature two straps rather than one. Some see this merely as a fashion statement, but it is really not. The purpose of the second strap is to give a better fit. Double monks are better for narrower feet because the second strap holds them more securely in place.

3. Cutaway Monks: The straps on traditional monks point downward towards the sole. Not so with a cutaway. The Cutaway’s straps tend to point back towards the heel. Cutaways can be either single or double strapped.

HISTORY

Through my research there is no exact date when the monkstrap shoes were first made. However, there is a connection to the life of monks in the middle ages.

The simple life of monks took place mainly in monasteries and close surrounding garden areas. The monks usually wore sandals, which soon turned out to be not very suitable for manual labor in rougher terrains. So, the sandal was transformed into a closed leather shoe with a buckle, the forerunner of today’s monkstrap shoe.

The monkstrap shoe was innovated in the late 19th century by English shoe maker Edward Green creating the style we know today. During that time, the monk shoe gained popularity in England, and it was often worn by gentlemen on formal occasions.

Well into the 20th century the single monk strap was the most popular choice but moving into the 20th century the double strap monk has become more popular. There are 3 types of designs in production today and are available by lots for major luxury brands as well as your custom shoe makers. The third design has 3 straps instead of 2 but in all fairness they are not very popular and in my opinion, I do not think they look good, it’s overkill.

PRESENT DAY

Today, monk strap shoes are an integral part of a classic gentleman’s shoe wardrobe and the double monks have even achieved a certain kind of mainstream appeal. When I was doing my research I read that in Mediterranean countries especially, men often wear partially or completely unbuckled double monks to underline their nonchalant look. Not sure how comfortable that would be because I like to have my monk strap shoes buckled up for comfort as well as being able to walk properly… it would be like walking with your shoelaces untied.

The experts say the monk strap style shoes are not appropriate for a black tie or very formal events however, they do say Oxford lace style shoes are preferred. The monk shoe, no matter what model you like, is a very versatile choice and can be worn in both business and casual settings. I think they work best with your suits, but will also work great with more casual wear like your chino pants or other casual trousers as well as jeans.

Another plus when it comes to buying a pair of monk strap shoes is they are available in all different price points. I recommend to anyone to find a pair that is made from a quality leather and as long as you take care of them the maintenance should be minimum. They can be a lifelong purchase.