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What is a Monkstrap shoe, and which should you be buying?

With a footing in function, these eclectic shoes have walked into the world of high fashion

The Monkstrap shoe has come a long way. Originally created as an alternative to sandals for European monks – a closed-toe shoe for wandering around breezy friaries and monasteries – today these sandal stand-ins have graduated to the rank of dress shoe. Crafted from the finest leather or suede, and with single or double buckles adoring their uppers, the Monkstrap has walked free from its functional origins and into high fashion – seen at Pitti Uomo or upscale society gatherings.

In fact, the Monkstrap has hybridised into some of the most eclectic and eccentric pairs of shoes available to buy today. With plain toe, brogued and even boot varieties cropping up, no man’s wardrobe is complete without a pair of Monkstraps – so buckle down, gents, and take a look at six of the best…

Plain-toe Monkstraps

The workhorses of the Monkstrap family, these simple shoes are the closest to the original monk’s footwear that you can find. But that’s not to say you can’t introduce a dash of luxury. Edward Green are leading the charge with their Fulham Double Monk-Straps, crafted in rich brown leather and boasting comfort beyond compare. Or, if you’re looking for single-buckled and suede, Ralph Lauren’s Purple Label have these hardy, leather-soled option – perfect for the workplace.

What is a Monkstrap shoe, and which should you be buying?

Edward Green Fulham Monk-straps

£1140

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What is a Monkstrap shoe, and which should you be buying?

Ralph Lauren Suede Monkstraps

£570

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Brogued Monkstraps

Upping the formal factor are the Monkstraps that boast brogue detailing. Extra flourishes on the toe cap and down the side of the shoe add even more interest than the double buckle, and O’Keeffe’s ‘Bristol’ is a perfect example. Expertly made in Italy from the label’s ‘Para Shine’ leather – a vegetable-tanned hide that’s meticulously polished by hand – and with Goodyear-welted soles that can be replaced when worn through, these are the perfect investment shoes, in brown or black.

What is a Monkstrap shoe, and which should you be buying?

O’Keeffe Bristol Monkstrap Brogues

£455

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What is a Monkstrap shoe, and which should you be buying?

O’Keeffe Bristol Monkstrap Brogues

£465

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Monkstrap Boots

Perhaps the most left-field variant of these staple shoes sees the Monkstrap blend with a boot. The single buckle brings simplicity, and the robust materials used by heritage shoemaker Edward Green ensure a solid and stylish boot. On Diane rubber soles for both grip and traction, these boots are not only uber-fashionable, but also display the functionality and durability that made the Monkstrap great all those years ago.

What is a Monkstrap shoe, and which should you be buying?

Edward Green Ravenstone Suede Monkstraps

£1090

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What is a Monkstrap shoe, and which should you be buying?

Edward Green Ravenstone Suede Monkstraps

£1090

Buy Now

Further Reading