We know why you’re here. You’ve seen the peacocks of Pitti swanning (too much bird?) around Florence and you want in. We’ve all seen the photos. Immaculate suiting, all sprezzatura sat on those trademark granite ledges. Zoom down and what do you see? Monk strap shoes. Of course there’s loafers and Oxfords knocking around but you’ve seen the monk straps and you want in. Welcome friend, you’ve come to the right place.

Let us guide you through an often overlooked but nonetheless timeless shoe. We'll talk you through the origins, the great one strap two strap debate, what to wear with monks and finally a quick guide to who makes the best men's monk strap shoes around.

What are monk strap shoes?

When it comes to the monk strap shoe, the origin is in the name. Unsurprisingly, monks, or a 15th century alpine monk specifically, is thought to be the source of the monk strap shoe. Several centuries ago when monks were putting in the hard hours at monasteries across Europe, they needed a stronger sandal.

When they weren’t in the chapel, they were taking part in hard labour and this pummelling work required sandals with the robustness and support of a shoe. This led to the innovative use of the strap and buckle fastening and the design soon took off, evolving into an inevitable closed toe version.

By the 1800s, shoelaces had replaced the humble strap and buckle. But monk strap shoes as we know them now experienced a revival and peaked in popularity during the 1920s. They’re seen as somewhat of a bold move these days but have again undergone a resurgence.

On a scale of shoe formality, a monk sits formally above a loafer but below an Oxford. Despite what people might have you think, a monk is actually closer in construction to a Derby. Available in round toe and square toe styles as well as a variety of materials, the monk is a versatile and extremely comfortable, Goodyear-welted middle ground between smart and casual.

Single vs. double monk strap shoes?

The ultimate question. Men literally fight tooth and nail over this very debate in menswear forums. It’s a real touchpaper topic. But, we’re brave so we’re just going to say it. Single strap monks are a more formal option than double strap monks. It’s as easy as that.

Single strap monks in black leather are arguably the most formal a monk can get, whilst double strap monks in brown suede are closer to a resort wear shoe or something casual to wear with jeans. Double monk straps lend themselves to smart events that still allow for personality, like weddings and summer parties.

Formal business events meanwhile lend themselves to a single monk strap with a more serious Oxford-style toe cap.

What to wear with monk strap shoes?

Despite sometimes being viewed as a bit of a sartorial statement, monks generally tend to go with most styles of smart-casual dress.

Touching on the previous single and double monk strap debate, a single monk strap in black with no toe cap is a great way to finish off a black suit. Ideal wear for important days in the office or similar high profile occasions. Darker, brown styles in calf leather also lend themselves to suiting, adding a welcome contrast to navy suits when worn with a matching belt. Most quality shoemakers will have the matching belt on hand.

Moving down the casual scale ever so slightly and you’re at the point where in our opinion monk straps really come into their own. Sprezzatura-style separates. Well thought out slightly casual tailoring with a break in the trouser, a pair of statement socks and then a double monk strap on the end of it. Perfection. It’s a tough luck to pull off but monk straps lend themselves to this sort of dressing.

Dare we say, as long as the leg isn’t painfully skinny or slim, monk straps even lend themselves to denim. Years of spray on denim twinned with double monk straps (and similarly skin tight tailoring in the recruitment industry) has tarnished the image of the monk. But done right, a brown suede or leather grain double monk twinned with selvedge denim really works.

You inspiration should be Drake’s rather than The Only Way Is Essex.

The best brands for men's monk strap shoes

Myrqvist

One of the many companies that’s cottoned onto the benefits of ditching bricks and mortar and selling directly to the consumer, Myrqvist deal in finely crafted, hand-made shoes made in Portugal. Said shoes are sold to you without the mark-up. Monks are a prime example. Available in single or double strap, taking in styles such as classic derbies as well as boots and loafers, Scandi design pragmatism is evident in the half rubber soles. Consider the Alsten in dark brown in French calf leather.

Velasca

If you’re on the hunt for sprezzatura, consider Milanese shoemakers Velasca. Built upon a love of Italian craftmanship, all roads led to the Marche region of Italy where shoemaking has been passed from generation to generation. The brand has built upon these centuries of expertise and skill. For an Italian-crafted single monkstrap that lends itself to the smartest of occasions, look no further than the Garzon. Available in black smooth calf leather, they’re the ultimate statement shoe.

Grenson

You can always count on Grenson to channel British heritage footwear with an all-important modern twist. It’s what sets the brand apart from their Northamptonshire counterparts. This is no more evident than in the monk strap department, with Grenson’s playful takes on the classics. The Hanbury is a triple-welted, high-shine double monk strap. The triple welt gives an almost commando sole aesthetic whilst still remaining formal thanks to a leather soul and rounded toe.

Church's

Still handmade in Northampton, Church’s is an iconic shoe brand that has been transformed since a certain fashion house took over upstairs. Excellent campaigns too. It’s the polished binder monk strap in burgundy that’s caught our attention. If you’re after a monk in a brogue style this one is a great bulky option that can be dressed up or down. Available in black too, the calf leather has a polished binder finish, Goodyear constructed storm welts and a leather double sole. A classy stomper indeed.

John Lobb

Very much sitting towards the top of Northamptonshire shoe royalty, John Lobb is a brand lauded for quality. One of the best brands on the planet when it comes to shoemaking. But what’s so great about John Lobb is they don’t sit still. Of course there’s the classics. The William is a truly classic double monk strap, with a design first conceived in the 1940s. Fast forward to the William 92 and you’ve got that design and the finest materials money can buy but with a rather dashing contrast stitch and chunky rubberised EVA soles.

Scarosso

You can always trust Italians when it comes to monks. They’ve made a name for themselves. Both making and wearing them. Scarosso is another classic Italian shoemaker using the finest materials whilst swerving the inflated bricks and mortar pricing. We’re very much here for the black on black Francesco Nero monks. Black calf leather, black buckles and black soles.

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