In the heritage-obsessed world of menswear, to refer to an item of dress as ‘classic’ before at least 20 years has passed since the first bloke plucked up enough courage to wear it out in public is to risk being stripped of your cufflinks and escorted off Savile Row.

However, when the monk strap shoe waltzed out of the friary and onto the front row of fashion week during the mid-2000s, even the most mulish of menswear curmudgeons could see that an exception had to be made.

Quickly adopted by everyone from puff-chested Pitti peacocks to style-conscious guys who just fancied a change from their Oxfords, the monk strap was an instant hit – providing a much-needed, fashion-forward alternative to the usual dress shoe suspects.

The History Of Monk Strap Shoes

Granted, monks are a pretty offbeat source of style inspo, so let’s just take a moment to be thankful it was the shoes that fashion chose to adopt and not the tonsure hairstyle. Although, having witnessed the man bun phenomenon first hand, it seems nothing is beyond the realms of possibility.

The monk strap shoe originated in Europe several centuries ago, when holymen conducting manual labour needed a closed-toe version of their sandals for added protection. After all, nobody wants a broken toe, even if there is an endless supply of mead in the monastery’s brewery to ease the pain.

The look later found its way into the public fashion consciousness. Leather shoes with strap and buckle fastenings became popular for quite some time through the 1700s and 1800s, before fading into relative obscurity as lace-up styles regained popularity.

The style evolved throughout the 20th century, but it wasn’t until midway through the noughties that the monk strap went mainstream and was quickly jumped on by the #menswear scene, propelling it back into the spotlight via a full-scale Tumblr assault.

Today, a sleek pair of monk strap shoes is the hallmark of the fashion-forward yet traditionally-inclined modern gent. Skirting the line between classic and contemporary with beautiful precision.

Monk Strap Shoes for MenOliver Sweeney

What Is A Monk Strap Shoe?

Sitting somewhere between an Oxford shoe and a loafer, the monk strap has the DNA of a slip-on, while retaining the tongue and vamp commonly found on its lace-up cousins.

In place of laces, monk strap shoes have their titular straps and buckles. Double monk straps are without a doubt the most popular, but single- and even triple-strapped versions do exist, offering even more scope for standing out from the crowd and catching the eye of a waiting street style photographer next time you’re swanning around Florence in your finery.

With that in mind…

Single Vs. Double Monk Straps

Single or double? It’s a debate that has provided the fuel for many a heated discussion in the menswear community. But are two straps really better than one?

It all boils down to personal preference. Single monk straps tend to draw less attention and therefore offer a touch more subtlety than their dual-strapped counterparts. A single-strap monk shoe is therefore better suited to a formal environment due to its clean, stripped-back appearance, while the ‘dub monk’ (that’s an abbreviation for ‘double monk strap’, not another name for a reggae-loving clergyman) is the stomper of choice for parties, weddings or any other occasion where your outfit permits a touch of personality.

How to wear monk-strap shoes

ReissBurtonMangoBrunello Cucinelli

Different Types Of Monk Strap Shoe

Just like its Oxford and Derby shoe relatives, the monk strap has more than just a few variations to cause the potential for confusion. Here’s what you need to know.

Classic

Similar in appearance to the plain-toe Oxford, the classic monk strap features minimal detailing, with the only stitching tending to appear between the vamp and the quarter, and also down the heel of the shoe. This creates a smooth, uncluttered appearance, making the classic monk strap the most formal of them all.

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Toe Cap

No prizes for guessing what this variation’s defining characteristic is. Yes, obviously, it’s a toe cap. The extra layer of leather stitched over the toe lends the shoe a businessy edge, which means if you want monk strap shoes you can wear to work, these are your best bet.

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Wingtip

For a less dressy alternative, a wingtip is the perfect option. Decorated with an W-shaped patch of leather stitched onto the top of the toe, ‘wings’ that can extend right around the sides of the shoe and broguing throughout, a wingtip monk strap makes for a slick, weekend walker.

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Monk Strap Boots

When the weather turns soggy, there’s no need to sour the look of your suit with a pair of wellies. Well, not when you have a pair of these bad boys at your disposal anyway. All the good looks of a traditional monk strap shoe, with the practicality and comfort of a boot. A fine, gentlemanly choice for winter.

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Casual

Lighter shades, rubber soles, hits of vibrant colour and suede construction are all elements that have helped soften the monk strap shoe’s dressy image and broaden its appeal. Feel free to rock a pair of these with jeans and an oxford shirt, or even a neutral suit for a summer wedding – we practically guarantee you some compliments.

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Buyer’s Guide

So, you’re sold on the merits of buying your first pair of monk strap shoes, but what should you be looking for when it comes to picking the right ones out? Cobbler-in-chief at Oliver Sweeney, Tim Cooper, loves these alternative kicks so much that he tied the knot in his. If anyone knows what makes a good pair, it’s him.

Soles

“The construction must be one with a name, like Blake-stitched, Goodyear-welted or a Bologna construction,” explains Cooper. “Definitely not a sole stuck on as this is not premium, comfortable or as stylish.”

Upper

Always go for real leather or suede if you want quality and durability from your footwear. Synthetic alternatives will look cheap and wear out fast. Remember, good shoes are an investment.

“For classic, opt for full-grain calf leather, as it gives a crispness to the finish. The monk should be a crisp shoe,” adds Cooper. “Lining as well should always be leather for both comfort and luxury.”

Buckles

“The buckle should be brass as it’s good quality and lasts longer than cheaper alternatives,” says Cooper.

If in doubt, have a play with it. A good quality buckle should feel heavy and solid – the last thing you want is it snapping five minutes before you’re due to step out the door, or worse, when you’ve already left.

The Best Monk Strap Shoe Brands

Now that you’re a bona fide monk strap shoe expert, it’s time to take a look at some of the best brands making these modern, menswear staples.

Kurt Geiger

Since the sixties, Kurt Geiger has been the British high street’s go-to for premium footwear. A focus on quality and a commitment to fair pricing has seen the brand cement its name as one of the best in the game.

From contemporary twists on classic silhouettes to trend-led styles capable of accommodating even the most forward-thinking of footwear fanatics, KG is most definitely the place to be.

Buy Now: £99.00

DIGBY in brown KURT GEIGER LONDON

Oliver Sweeney

Lovingly designed in London and carefully crafted in Italy by the hands of some of the world’s finest shoemakers, Oliver Sweeney’s footwear is in a league of its own. Mixing traditional craftsmanship with contemporary design, the brand’s artisans create shoes that challenge convention without compromising on comfort.

With premium features such as Blake stitching, Goodyear-welt construction and even the option of tattoo personalisation, a pair of monk strap shoes from Oliver Sweeney is a pair like no other.

Buy Now: £329.00

TONI BLACK Calf Leather Double Monk

Aquila

Born in 1958, this heritage Australian brand has Italian craftsmanship in its DNA. It uses traditional construction techniques and fine leathers but doesn’t shy away from contemporary updates of classic designs.

Its monk straps come double-strapped, toe-capped, brogued, wing-tipped or even rubber soled. They all look great.

Buy Now: £117.14

Aquila monk straps

Paul Evans

Designed in New York, made in Naples and delivered to your front door, Paul Evans is a brand that eschews the boring traipse down the high street for a more bespoke service.

It makes proper monk straps, solidly built, classically designed, well heeled. Available in boots, single- or double-strapped, too.

Buy Now: $399.00

The Poitier Double Monk Strap

Suitsupply

The one-stop-shop for all your formalwear does an occasionally overlooked line in excellent footwear made from the best Italian leathers, and using traditional construction techniques like Blake stitching. In other words, they’re built to look good and stay that way.

Gorgeous suede options aside, the chunky monk strap boot is an excellent choice. Fully leather-lined, it’s flexible on the foot and will age better than you most likely.

Buy Now: £229.00

suitsupply brown boot

John Lobb

One of Northamptonshire’s finest cobblers, this shoemaker has been in business since the mid-1800s. And the brand’s experts take their time – each pair goes through 190 steps with Goodyear welting giving you what should be a lifetime of stomping around in style.

In terms of the finish, think classic, with minimalist stitching and punching, rock-solid soles and elegant buckles.

Buy Now: £895.00

John Lobb William monk straps

Topman

Pick out a pair of monk straps from Topman’s dizzying array and you’ll be laughing all the way to the bank, wearing a great-looking pair of shoes as you go. The combination of variety, value for money and quality offered by this high-street hero is unparalleled and with prices being as low as they are you could even treat yourself to a second pair.

Hard to beat if you’re on a budget.

Buy Now: £49.00

Tan Leather Luther Monk Shoes

Grenson

Founded in 1866, Grenson is one of the oldest Northampton shoemakers still operating today. This heritage is clear to see in the label’s designs, where traditional, British styles are upgraded with contemporary touches. Think classic broguing alongside modern, rubber, wedge soles.

Old-meets-new is the name of the game here, making Grenson the modern gentleman’s go-to brand when it comes to choosing footwear with the power to transcend trends.

Buy Now: £225.00

Grenson basil monks

ASOS

Online heavyweight ASOS has taken the retail world by storm and if you’re looking to pick up certain styles without breaking the bank, then it’s difficult to think of anywhere better suited. The company’s own-brand monk shoes offer all the good looks at a fraction of the price, so you can put a pair on without wincing at every step, thinking of how much you paid.

Buy Now: £40.00

ASOS Monk Shoes In Black Suede With Distressed Sole

Reiss

Proudly sitting at the upper end of the high street is Reiss – a brand that is certainly no stranger when it comes to premium quality clobber. The label’s sleek, stylish aesthetic and ease of access have earned it fans ranging from inner-city fashionistas, all the way up to the Hollywood elite.

If you’re looking for premium build from the comfort of the high street, Reiss is the place to go.

Buy Now: £185.00

REISS RILMONT DOUBLE MONK STRAP SHOES DARK BROWN

Marks & Spencer

Is there anything as quintessentially British as good old M&S? Perhaps not. The historic retailer has been a staple of every UK town and city for as long as any living person would be able to remember. And for good reason, too.

M&S gear is built to last, not just in terms of quality but also in terms of style. Fleeting trends and shoddy construction are two things that simply don’t exist in the world of Marks & Sparks, and here in 2018, that really is a rare and beautiful thing.

Buy Now: £75.00

M&S COLLECTION Leather Single Strap Monk Shoe

Base London

In 1995, the folks over at Base London embarked on a mission to create stylish footwear capable of meeting the new and complex set of demands laid out by the modern man. Fast forward 20 years and it’s clear to see they succeeded. Base London is now one of the best established shoe brands in the UK and with an unparalleled bang-to-buck ratio, it’s the perfect place to pick up your new pair of monk straps.

Buy Now: £72.99

Base Monkstraps

Church’s

It may be owned by Prada, but Church’s is actually one of the original Northampton shoemakers. Established in 1873, the brand prides itself on its esteemed footwear heritage and its implementation of traditional manufacturing techniques that have been passed down from generation to generation over the course of hundreds of years.

Today, Church’s are still regarded as some of the finest British-made shoes money can buy and the moment you try a pair on for the first time you’ll understand why that is.

Buy Now: £646.00

Churchs Shanghai monk shoes

Aldo

Founded in Canada in 1972, high-street shoe retailer Aldo quickly took the world by storm – and it’s easy to see why. The footwear is made with quality materials, it’s well put together and manages to skirt that notoriously tricky line between timeless and contemporary with ease.

Buy your new monk strap shoes from Aldo and you can be assured you’re getting the best quality and most stylish looks for your hard-earned cash.

Buy Now: £95.00

ALDO Ales Brogue Monk Shoes In Black