Looking for stylish dress shoes that stand out from the crowd? Try out a pair of monk straps!
Despite their supposed spiritual origins (which we’ll get to later), monk strap shoes can easily have a uniquely heavy metal aesthetic as far as dress shoes go. Don’t get me wrong.
They’re still elegant and highly sophisticated, monk straps being one of the main dress shoe styles along with Oxfords, loafers, and derbies.
However, they can more easily be worn in casual contexts than most dress shoes. Depending on the design, a pair of monk straps can literally be worn with a tuxedo or ripped jeans — if that’s your thing.
The hardware provides an aesthetic connection to even workwear pieces sometimes. Now that’s unique.
Short on time? Here are our top picks for the best monk strap dress shoes you can buy:
A perfect combination of sophistication and versatility. Not only do they make a bold fashion statement, but they also provide unexpected comfort that is rare in a dress shoe.
With a unique and minimalist wrap-like aesthetic, these shoes will elevate any outfit. The leather is surprisingly good quality for a sub-100 price tag, making these shoes a steal for any budget-conscious fashionista.
Thee simple and classic design has remained unchanged since the 1940s, which is a true testament to their ability to stay in fashion.
If you want more options and details, here’s the full list…
What Are Monk Straps?
The defining feature of monk strap dress shoes is that you buckle them closed via their strap or straps. They work more like belts, as opposed to the typical lacing system. Monk straps can have one, two, or even three straps per shoe.
Supposedly, they get their name from the fact they’re descendants of the strapped sandals worn by 15th-century monks in the Alps.
When it comes to detailing, they’re generally more adorned than Oxfords (hardware and all), but more minimal than derby shoes. They’re still dress shoes, but moderate ones that can easily be worn with jeans or a black-tie combo, depending on the design.
Best Monk Strap Shoes
You’ll find that monk straps are impressively versatile (even shoes with more “busy” designs).
Here are some great monk strap shoe options:
Allen Edmonds Plymouth Single Monk Strap
The Allen Edmonds Plymouth Single Monk Strap is definitely an investment shoe, but also a more reasonable investment shoe, given the insane designer prices on the market.
With the Plymouth, you truly do get your money’s worth with the quality of the materials, the construction, and the refined design.
It flaunts sleek lines but with a rounded toe, providing the quintessential balance of relaxed and dressy that you go to for monk strap shoes.
The walnut colorway can be worn with most outfits, while the blacks can be worn with essentially any outfit (including tuxedos and excluding athleisure, of course).
Speaking of the toe, this shoe is made using the brand’s 201 last which provides more room in the forefoot, so there’s almost a Narnia of space. It’s comfortable but is still visually slim.
They’re made from lush European calfskin, chosen for its tight grain and high strength-for-weight ratio. The surface is so well-oiled, that even the hue on the black version is more lustrous, compared to the blunt color of most black shoes.
And as this respected heritage brand does, these guys are 360 Goodyear welted, ensuring they’ll last you as you’ll take care of them.
Johnston & Murphy Reece
If you aren’t afraid of details, the Johnston & Murphy Reece is highly brogued and features two straps with buckles but isn’t loudly maximalist by any means. It pushes the boundary but still has an everyday wearable quality with its distinctness.
The perforations happen throughout the surface, giving them a more minimal look than if they were only on the seams. It’s definitely “a look,” but it’s not costumey.
It’s also closer to the budget end of shoe prices, making it a relatively safe price bracket for experimentation, without dipping too far into cheap fashion shoe territory.
The Reece is hand-finished in Italy with calfskin, inside and out, each individually patinated.
Saint Laurent Stan Monk Strap
I bet you didn’t think a triple-strap monk shoe could look so sleek.
The Saint Laurent Stan Monk Strap, a decidedly premium shoe, is adorned with three thick straps, each buckled. These buckles take up the entire upper vamp.
All of this hardware could result in a biker look, but the tip is knife-sharp and the silhouette is refined and skinny. That, along with its low collar and dress heel brings a beautiful balance.
If this shoe were a person, it would be one that was a member of a motorcycle gang that then went to reform school and put on a tux.
The black calf leather is exquisite and supple. The very same material is even used for the lining, so this shoe is about as posh as it gets while still having a touch of fashion-forwardness.
Ace Marks Kurt
Not only are the Kurt Monk Strap Shoes super chic and versatile on the style front, but they’re also surprisingly comfortable for a dress shoe.
Uniquely, this comfort factor comes not from some hybrid footbed, but from the shape of the shoe. Ace Marks has an in-house last built to diminish the effects of the added pressures on the ball and heel.
The break-in period is quite short, and I’ve even heard reports of zero break-in.
Between that and the Blake-stitched construction, which though not as commonly practiced as a Goodyear welt is still resoleable, this shoe has a lot more flex right out of the box.
And of course, these handcrafted shoes are made in Italy (by fourth-generation artisans, no less), and are built using beautiful full-grain leather. Even the dying and burnishing is done by hand. So like a piece of art, each pair is slightly unique from the other.
Johnston & Murphy Archer
Count on Johnston & Murphy to serve up a pretty decent pair of low-cost monk straps. It’s actually a challenging design to implement on a budget, considering all of the potential bad cuts that can happen with the extra leather taking the place of laces.
With the Archer, they cleverly get around this by using one large piece of leather over the top, which then breaks off into two pieces where the buckles are placed. From the aerial view, it has a wrap-like aesthetic, which is unique and minimalist.
The leather is pretty good considering the sub-100 price point, and it comes in a classic black and a cognac colorway.
Beckett Simonon Leonards
Thanks to Beckett Simonon’s small-batch system, the Leonards are a full-grain leather, hand-made shoe at the same quality of a shoe double its price — you might have to deal with irregular wait times though.
Still, if you have the time, this shoe is more than worth it. The toe is a bit rounded, but the shape is slim and dressy.
You can definitely wear them with jeans and a t-shirt, and you can definitely wear the black versions in the most formal of situations.
The single strap design is clean and elegant, but not without personality. I love how there’s another piece of exposed leather right beneath the buckled piece, giving it a nearly asymmetrical look akin to a moto jacket’s zipper design.
Meanwhile, the outsole is made out of leather for a classy and eveningwear-appropriate look, but it’s equipped with functional rubber caps which provide grip and support.
Even more, the premium calfskin leather comes from gold-rated tanneries approved by the Leather Working Group for sound environmental practices.
Beckett Simonon Hoyts
Being Beckett Simonon’s double-buckle monk shoe counterpart to the single-buckle Leonards, the Hoyts are a lot like the Leonards. It boasts the same Gold-Rated full-grain leather construction, the Blake-stitched soles, and even that rubber support cap.
With its extra buckle and its cap-toe, however, it’s a touch more detailed while still maintaining that adaptable formal look.
The toe box is almond-shaped which mercifully gives you tons of hidden extra space. The shoe is dressed up and sleek look though, thanks to its graceful taper and thin profile.
Another great combo? This shoe is built with a steel shank, riveted to the outsole and insole, which ups the support and balance factors.
And despite a stiffer construction, the interior is lined with comfortable, temperature-regulating Vachetta leather. Once broken in, this material will accommodate your specific foot’s anatomy.
Crockett & Jones Savile 4
As its name indicates, the Savile 4 Monk Strap Shoe flaunts that Savile Row level of expert and individualized craftsmanship that simply doesn’t exist anymore.
Crockett & Jones handpicks European calf hides that go into making this distinguished and beautifully grained leather.
The high level of craftsmanship includes a process in which aniline dye is used to create vibrant colors that are resistant to fading but will develop a unique patina over time.
Of course, they’re Goodyear welted and hand polished in Crockett & Jones’ factory in Northampton, England as well.
They also offer repairs, so you can rest assured that the very same experts who built the shoe know exactly what goes into rebuilding any part of it.
The whole-cut vamp and open quarters give a refined, layered aesthetic, as does the softly-squared toe. There aren’t a lot of hard edges on this design, making them easy to wear with most combinations.
The Orwell shoe by Herring is almost like a men’s Victorian-era high-heel shoe but tempered to fit modern standards. With its high collar and substantial heel, this shoe truly has a grand look about it.
It’s essentially a dress Chelsea but with straps. This chiseled piece of footwear is hand patinated in the Carlos Santos factory in Portugal, known for its premium and luxury-level leathers.
As always, this means each pair has a unique visual character to it, whether you go for the black version or the brown variant which has a beautiful murky quality that combines mahogany hues with dark warm browns.
If you’re looking for a high-quality shoe that’s decidedly fancy, but not overly dandy, the Orwell strikes this balance in a truly unique way.
Thursday Boots Saint
Thursday Boots came about because the founders wanted to build boots that are as good-looking but way more substantial than fashion boots and are as strong and long-lasting as often-clunky work boots. Unsurprisingly, their foray into dress shoes carries on that philosophy.
The Saint is made out of full-grain leather that’s undeniably premium, especially for its price, and is even Good-year welted.
It’s a brawny dress shoe in that sense but also features cork midsoles and shock-absorbing insoles that work together to give you comfort, protection, and personalization.
You can basically wear this shoe right out of the box with little to no issues.
And on the style front, it mixes a refined shape with a cap toe and double buckles, allowing you to wear them in the most casual situations without compromising their formality. You can even wear these with certain workwear pieces, like a fitted utility shirt.
Something to note is that each version varies in more than just color.
The black colorway is more rounded, compared to its squared-off cousins, while the distressed gray flaunts extra texture and variated burnishing, making it even more casual.
Ralph Lauren Asher
Ralph Lauren is classic American, and there’s nothing more classic American than being inspired by old England.
The Asher shoe is essentially a modern take on English bench-made boots, which is why they look a bit like a more casual version of the prior-mentioned Crockett & Jones Shoe.
Its shape sweeps more than it tapers, with a more rounded version of an almond toe, and a substantial outsole that extends substantially past the aerial silhouette. The outsole is a bit boot-like, in that sense.
It has that perfect combination of elegant and athletic qualities that lets you wear it with a suit in the city, or out for a walk in the countryside. Classic RL.
The insoles are padded for comfort, while the treaded Vibram outsole serves up some pretty impressive traction.
Herring Lawrence Monk Shoes
There’s two breeds of upscale style. There’s the chic and fancy kind, akin to a brand new downtown high-rise, and there’s the traditional and classic kind, like a pre-war uptown brownstone.
The Lawrence Monk Shoes from Herring combine these two vibes, resulting in a truly stately, downright aristocratic-looking shoe.
Its vamp is simple and minimal, giving you that effortlessly elegant look like that of a slipper dress shoe. Relatedly, the toe tapers thinly, stopping short of a true point and opting instead for a rounded shape.
Meanwhile, the strap itself is thin, held tight by a square buckle, while the collar features a dip, similar to a Mandarin collar.
Since this is Herring, it’s made out of the best leather on the market, built and hand-patinated in the Carlos Santos factory in Portugal.
Ralph Lauren Darnell
The Ralph Lauren Darnell is a monk strap shoe for those who prefer loafers.
The collar is so low, you can actually slip these on and off, while also offering a relaxed yet dressy look thanks to its flat profile and its straight, moderately tapered silhouette.
And while the design and shape sit somewhere between smart and smart casual, the materials and build are 100% premium and exceptional.
Ralph Lauren lines range, but the Darnell is real Italian calfskin, exquisitely burnished. The buckle is sophisticated and features beautiful detailing.
The padded leather insole is comfortable and will conform to your specific foot shape, while the elegant leather outsole is strong and handsome.
The Prince from Taft checks all of the boxes for a premium shoe: Goodyear-welted construction, a full leather lining, a stacked sole, and excellent French calfskin leather.
It’s as good-looking and long-lasting as any high-end shoe.
What makes it stand out is its distinguished criss-cross design. The two straps intertwine, making it bold and interesting, but their square shape gives it more of a Tetris architecture, versus an actual ‘x’. It adds an unexpected character without being too weird.
They also have a pretty wide range of sizes, going as small as a 6 and as big as a 15.
John Lobb William
Finishing this round-up off is the aspirational John Lobb William, which is probably one of the best monk strap shoes on the market.
It has a simple and classic design, unchanged since the 1940s, so you know that it has a good track record of staying in style. It’s like the Rolex Submariner of monk strap dress shoes.
And like the Sub, it combines form and function. The full-grain leather is supple and, honestly, perfect. Meanwhile, the buckles boast a palladium finish, which is a rare type of platinum that’s less dense so it doesn’t add any bulk.
This double-buckle shoe is fully lined, and no surprises here is built with a Goodyear welt, making this shoe a real “buy-it-for-lifer.”
Here are some answers to some commonly asked questions about monk strap shoes:
Are monk straps out of style?
No. Monk straps have gone in and out of style since the beginning of the 20th century, but have made the rounds enough that they’re officially classics. There will be eras in which they’re more or less popular, but they’re essentially timeless.
What are the different types of monk straps?
Monk straps often come as a one or two-buckle design and, rarely but not impossibly, as a three-buckle design. Some are made with leather and others suede, with various levels of details such as broguing.
What are monk strap shoes good for?
Monk straps are versatile dress shoes. The hardware makes them perfect for both casual and formal situations. The fewer details there are on the shoes, the better they are for dressier occasions.
As you can see with monk strap shoes, a lot of variations can come out of a simple design concept.
When it comes to how it affects your wardrobe, one important thing to consider is whether the specific monk shoe you pick leans more into the relaxed side or the dressy side of the spectrum.
Another thing to consider is how monk straps, with the exception of those that use their clever proprietary roomier lasts, are naturally more narrow and might need more breaking in.
Still, you can get a lot of mileage out of this truly versatile dress shoe style.
Questions? Comments? Leave them below!
Ask Me Anything