According to legend, an English traveler met a monk from the Alps in the 15th century who had created a unique form of sandal. He instantly took a liking to the design, made a note of it, and returned to England. The new design was an instant hit, and became popularly known as the monk strap ever since.

In reality however, the origins of the monk strap shoe are unclear, although it’s likely that the design is around 250 years old. The shoe reached the height of its popularity around the 1920s, but the monk strap’s recent resurgence means that it has found a new lease of life as a stylish, modern footwear choice.

Remarkably comfortable on the foot, and similar in construction to the Derby shoe, the monk strap can in many ways be considered as the Derby of the modern day. A well-chosen monk strap can add a touch of old-school sophistication to any man’s wardrobe, whether you’re wearing them with a sharp suit, or simply smartening up a casual outfit. For these reasons, we’ve compiled a selection of the best monk strap shoes out there. Take a look below…

Carmina

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These brown double monk straps from Carmina (£379) are a reliable option for pairing with any smart outfit. Those who are new to the monk strap will fare best with the darker brown colour, although more seasoned wearers should feel free to experiment with the lighter tan shade. A simple yet elegant choice, wear it with a smart blazer, shirt and trousers for the best effect. Ultra-formal outfits such as the tuxedo, however, are generally an area to steer clear of when it comes to the monk strap.

Crockett and Jones

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Part of their Main Line collection, the Lowndes double monk strap by Crockett and Jones (£425) is the priciest option on our list, but it will exude minimalist quality when paired with a super sharp black suit. Entirely made in Northampton, England, the Lowndes uses a leather sole with open stitching, stained and waxed to provide protection from the elements. Avoid incorporating navy and brown tones into your outfit when sporting a black monk strap – go for the Carmina above if that’s your plan.

Tricker’s

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The lightweight Rufus double monk strap by Tricker’s (£395) is the ideal shoe for slightly more casual attire – wear with a stylish pair of chinos for the best effect. While the brown colour is the safer option, those wishing to stand out from the crowd may prefer to sport the Rufus in navy. If this is the case, avoid black, and instead pair with smart grey trousers for a bold look.

Bonus: Scarosso

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For a slightly more affordable option that’s still bringing some serious quality, look no further than Scarosso’s Francesco Moro monk strap (£195). Hand crafted in Italy, the Francesco Moro is made from dark brown calfskin, with a natural coloured lining in goatskin and a light rubber sole. If brown isn’t your first choice, check out the Francesco Nero (also £195) for the same design in black.