The Ultimate Guide to Monk Strap Shoes: Buckled-Up Adaptability

Shoebly is supported by readers. When you buy through our links, we may earn a commission. Learn more.
by  Karlton Miko Tyack | Last Updated: 
monk strap shoes - beckett simonon hoyt & beckett simonon leonard shoes

When it comes to selecting a dress shoe as part of their shoe rotation, many guys simply opt for some standard oxfords and call it a day.

They’re classic. They’re more formal than loafers. They’re probably the most versatile, right?


Allow me to introduce you to the humble monk strap shoe.

The lack of lacing but the addition of hardware makes them more minimal than other dress shoes in some ways, but more detailed in others. Monk straps can do everything your oxfords and loafers can, and even pick up more slack by doing a lot of the things boots can, too—at least, style-wise.

Intrigued? Good. Read on.

What Are Monk Strap Shoes?

Monk strap shoes are dress shoes, usually leather, featuring straps secured by buckles. These straps are like belts in place of traditional laces. Monk strap shoes can have multiple belts, but most often feature a one-strap and two-strap design. 

Along with oxfords, derbies, and loafers, monk straps are definitely in the common, core group of dress shoes.

They’re more detailed than most oxfords and less detailed than most derbies. So, monk straps are considered the middle-ground, less dressy than the former, but more so than the latter.

Still, even in casual contexts, you can get a lot more mileage out of monk straps compared to derbies. The fact there’s hardware on monk strap shoes gives them a visual bridge to certain workwear-inspired pieces, a rare quality for dress shoes.

Ironically, even though monk straps are the closest thing to metal-as-hell when it comes to traditional dress shoes, they actually get their namesake from monks. You know, the praying, meditating kind.

Modern-day monk strap shoes resemble, and may have been inspired by, strapped sandals worn by 15th century monks when plowing the fields in the Alps.

Since there’s no lacing, monk strap shoes can often be pretty narrow, so they might need a bit more breaking in, especially if they’re Goodyear welted.

If that’s a concern for you, I think a Blake-stitched monk strap is still a pretty exceptional choice. I feel similarly towards Blake-stitched, whole-cut leather shoes. The uppers of these styles are so narrow and lack flex points that a Goodyear-welted version could potentially keep it quite tight even after break-in.

Look at the Beckett Simonon Leonard, as an example. With its slim silhouette and full-grain leather build, it’s one of the chicest and most adaptable monk shoes on the market.

It’s Blake stitched, but also features a steel shank. This means the break-in will be quick and moderate, without compromising its sturdiness or its resolability.

Beckett Simonon Leonard

The Leonards have a classy, minimal look thanks to their single-strap, clean-toe design. And since Beckett Simonon uses a small-batch system, these full-grain leather, handcrafted shoes have the quality of footwear double their price.

Check Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Single vs. Double Monk Strap Shoes

Let’s dig a little deeper into the two main types of monk strap shoes: The single monk shoe and the double monk shoe.

Inherently, all monk shoes balance formality and casualness. However, a single monk strap is generally more formal than a double.

The more details a shoe has, the more casual it is. Compare the previously mentioned Beckett Simonon Leonard, their single-strap monk, with their double-strap, the Hoyt. They’re both excellent shoes that I highly recommend, and you can wear both with jeans or dress trousers, but the Hoyt would definitely look better in a casual context than the Leonard.

Beckett Simonon Hoyt Monkstraps

Crafted from Italian full-grain leather and with a classically refined last, the Hoyt is an exceptional showcase of the double monk style.

Check Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Remember when I said that the hardware on a monk strap gives it a touch of a workwear vibe? Well, the more straps there are, the more buckles, and the more hardware. Additionally, the Hoyt has a cap toe.

Of course, other details, like buckle style and toe shape, will affect how detailed a shoe looks beyond the strap number. With a monk strap shoe, though, the strap style is the foundation of this, since it’s the dominant aesthetic component.

Taking it a step further, let’s look at the Ace Marks James, another well-built shoe. The full-grain leather and burnishing are truly exquisite.

The James not only has that added second buckle, but it has even more detailing throughout its upper than the Hoyt because of all the stitching. 

From most to least dressy, you’ve got the Leonard, the Hoyt, then the James. The more formal your outfit is, the more you’ll want to stick to shoes like the Leonard. The more relaxed it is, the more you’ll lean into shoes like the James.

Ace Marks James

The Ace Marks James are undeniably premium boots, hand-made in Italy using 100% full-grain calfskin. Combining the best of both worlds, they’re as tough-looking as boots but as classy as dress shoes.

Check Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

5 Ways to Style Monk Strap Shoes

At this point, I’m not sure how many times I’ve mentioned that monk straps are the kind of dress shoes you can wear casually or formally. 

Remarkably, certain variations of monk strap shoes can be wildly casual to an extent few dress shoes can. This Lethato Triple Monk, for example, is a rare instance of a three-belt monk. Aesthetically, it’s somewhere between cowboy and workwear, while still maintaining that dress shoes silhouette.

So yes, monk strap shoes come in a wide range of variations. Even wider is the range of different ways you can style them.

Here’s proof of that.

Lethato Triple Monk

With a seldom-seen triple strap and a notable blend of style and comfort, these Triple Monk Strap boots are here to redefine your footwear fashion! Straddling an aesthetic somewhere between cowboy and workwear, while still maintaining that dress shoes silhouette, they look great with a suit.

Check Price
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Pair Monk Straps With Any Suit and Tie

Suits and ties are what monk straps are technically made to be worn with. Still, you can always add your own personality. Suit style can be more fashion-forward, like the first example here. Or it can be less stuffy, like the second.

This gent tone matches his leather monk straps to his gloves, but avoids being too matchy-matchy by going for subtle patterns on his suit and bolder patterns on his jacket. This results in the shoes and gloves almost anchoring the entire look.

Even suede monk straps can go with a suit. This outfit follows all of the tried-and-true rules of “dressed-up relaxed” established by the Northeastern country club set. 

By that, I mean every piece on him is formal, but a laid-back version of it: The broken suit, going for navy instead of black, and, of course, brown suede instead of black leather.

Add Touches of Sportiness to Your Suits and Suit Separates

Pairing your suit with a quilted hunting vest is a true Wall Street staple. Monk strap shoes, with their dressy shape and metal hardware, also embody that aesthetic. Naturally, they pair well with likewise sporty-but-formal combinations.

This outfit has a lot in common with the monk strap concept, in that the silhouette is formal, but there are details that give it some topography and personality. 

His (possibly) wool pants have cargo pockets, while his nylon shirt jacket effectively replaces a blazer.

Is a safari jacket basically the outerwear version of monk strap shoes? This outfit sure makes the case for it. Again, this is an effective combination of outdoorsy and dressy, for that gentleman pheasant hunter vibe.

He gets extra points for going for suede shoes so that his jacket isn’t the only thing on him with texture. Excellent attention to detail.

With Fashion-Forward Combinations

If you love bright, lively colors or trendy pieces and fits, monk strap shoes can serve as a grounding force in such combinations. They add a bit of classicism but are far from being overly traditional.

This gent is going bold in all of the right ways. He leans hard into the striking red, which feels natural with blue. However, instead of going for an equally primary-leaning hue for his sweater, he chooses a dark navy that tempers the look without detracting from the eye-catching quality he’s obviously going for.

Cleverly, he finishes the look off with another spirited contrast: Full-on white suede shoes that are tonal with his shirt, just peeking out of his sweater.

This is another combo that seems tailor-made for monk strap shoes. Each element of the outfit is classic, with a twist. There’s a loose and flowy feel to the overall shape, with structure in select pieces, the monk straps and the jacket, for example.

Workwear-Inspired Casual

Love textures and pockets? As I hinted earlier, monk straps go beautifully with certain workwear pieces and denim.

This outfit was clearly put together by someone who had a lot of fun doing it. 

The denim on denim is accented with stylistically contrasting pieces like his beret and cravat, brilliantly tonal with his socks, and, of course, those high-polish black monk straps.

A more broken-up denim aesthetic, this look proves that even black leather monk straps can be worn casually. The jeans are more straight and relaxed, but this outfit would work perfectly even if you went for a more fitted version of it.

With the leather moto jacket and wide-legged cargo pants, instinct might lead you to finish this combo off with some boots.

However, with the classy turtleneck, the monk straps cinch the high-low approach this outfit achieves. 

Elegantly Casual

Ok, but what if you’re not into denim or workwear or textures? You can always wear your monk straps with a fitted T-shirt and cuffed chinos. Or, you can do what this guy is doing:

A Mandarin neckline and fitted but softly tailored pants go beautifully with his monk straps, every garment being classy yet relaxed. 

There’s structure where there needs to be, but the ensemble is otherwise minimal and understated. The slight heathering on the pants is a nice touch.

3 Things to Avoid When Wearing Monk Strap Shoes

Again, monk straps have a wide range. However, there are three strict rules—commandments, if you will—to ensure you aren’t abusing this versatility.

  • Stick to simpler variations if wearing monk straps with a tuxedo. A highly-detailed, distressed leather triple monk strap shoe? That’s a hard and fast no in formal situations.
  • Yes, you can wear your monk straps casually. However, under no circumstance should you partner them with athletic wear. Chino shorts and sockless monk straps? Sure. Basketball shorts and monk straps? Absolutely not.
  • As with any accessory, think about the color. This is slightly related to the formality rule. Again, a distressed gray would look inappropriate with a tuxedo. Subtle contrasts are always good, like tan shoes with olive pants. And, of course, bright hues, especially primaries (a bright red leather, for example), won’t be as adaptable as trusty neutrals like brown and black. 

Strap In, Buckle Up

Truly, there are few dress codes that monk straps wouldn’t be welcome at. And as previously mentioned, they can be styled like so many other types of shoes.

Sure, you can wear some boots with that leather jacket and denim pants combo, and you can definitely go the oxfords route with your work suit. And while you can’t trade the shoe choices between those two outfits, you can replace both with a nice pair of monk straps anytime.


Are monk strap shoes still popular?

Yes, always. Monk strap shoes go in and out of being the most popular dress shoes, the aughts being an example of one of their primes. However, they’re classic, and they’re never irrelevant.

Why are they called monk strap shoes?

They’re called monk strap shoes because they resemble the two-strap sandals that monks in the Alps wore in the 15th century.

Are monk strap shoes formal?

Yes, though they’re less formal than most oxfords, monk strap shoes are traditional dress shoes that can be worn in formal and professional situations.

Can you wear monk strap shoes casually?

Yes, monk strap shoes can be worn casually, including with jeans and even shorts.

Join the Discussion

Your email address will not be published. Required fields are marked *