5 Best Monk Strap Shoes for Men in 2021 and How to Wear Them

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William Barton Avatar by  William Barton | Last Updated:  Mar 21, 2021

Monk strap shoes are an amazing option for adding flair to your style, but there are so many to choose from.

In this guide, we’ll show you the best monk strap shoes in every category and even give you a few pointers on how to rock them with style.

Best Double Monk Strap
  • Calfskin upper with full leather lining is soft and patinas nicely
  • Blake-stitching for a slim, European style silhouette
  • Leather sole features durable rubber insert and stacked rubber heel for comfort
  • 30% off your entire order using code SUMMER30
Best Single Monk Strap
  • Thick full-grain Argentinian leather
  • Comfortable Vachetta leather lining
  • Unique toe box from proprietary Beckett Simonon shoe-last
Best Brogue Monk Strap
  • Hand-burnished, Italian calfskin leather
  • Goodyear welting for easy resoling
  • Rubber sole with cushioned insole for extra comfort
Best Luxury Pick
  • Made on the iconic Alden Aberdeen last
  • Water-lock outsole that repels water
  • Calf-skin upper and full glove leather lining looks rich and feels soft
Best Budget Pick
  • Frequently on sale
  • Square toe box for a unique look
  • Cemented construction and rubber sole, which is less expensive

A few years back, I took a trip to Italy. 

My goal was to bring back three things:

  1. A bottle of Tuscan wine
  2. A collection of ravioli stamps
  3. The best monk strap shoes I could find

Well, I spent a little too much time exploring my wine and ravioli options and I was rushed in the last few days to find my dream pair of shoes. 

But while window shopping, I found the perfect looking pair.

They practically vaporize my feet every time I wear them, so recently, I went on the hunt for a new pair of monk strap shoes that are comfortable and stylish. 

And I ended up getting some, too. 

So here are my favorite monk strap shoes—I’m confident you’ll find your perfect pair on this list. 

What’s the Difference Between Double Monk Strap and Single Monk Strap Shoes?

The biggest difference is pretty obvious: you get two straps or one. But let’s go a little deeper.

Double monk strap shoes are more common and typically have a piece of leather that buckles over your instep. 

MGemi Monk Strap Shoes 2

Two smaller straps are buckled in along the outside of your shoe. 

With a single monk strap, you’re usually getting a larger strap and buckle. They’re seen as more formal because of the cleaner, bolder lines. 

Monk strap shoes follow the basic style-etiquette guidelines other dress shoes follow:

  • Darker is always more formal, with black being the formal color of choice.
  • Polished is more formal than unpolished.
  • Can be worn with a suit and tie.
  • Can be worn with a black tie outfit (if they’re black). 

But monk strap shoes have a little more flair than your standard oxford. While they’re an excellent choice for hitting the office with a suit and tie, think about how you can weave your monk straps into a casual outfit. 

MGemi Monk Strap Shoes 6

Both single and double monk strap shoes will pair well with jeans, or try rolled chinos for some European panache.

5 Best Monk Strap Shoes for Men

1. M.Gemi Tommasso

model wearing mgemi tommasso double monk strap shoes feet dangling

M.Gemi crafts their shoes in the spirit of Italy. The brand’s namesake and founder, Maria Gangemi, grew up near the luxury shoe factories of Sicily. After decades of designing shoes for other US-based companies, she struck out on her own.

The Tommasso is now my fifth pair of M.Gemi shoes. The timeless double monk strap design, luxe calf skin leather, and slim Blake-stitched silhouette make these my top choice.

What We Like

  • The rounded toe is an excellent balance between formal and casual.

  • The beautiful calf-skin leather feels and look rich.

  • Blake-stitched soles give this a slimmer, more European vibe.

  • Rubber insert and heel lend much more durability to the shoe, but it still has a leather outsole for more formality.

What We Don’t Like

  • M.Gemi only offers the Tommasso in two colorways: chestnut, and black. I’d love to see a darker brown.

What Other Reviewers Say

Ordering through M.Gemi is easy and customers are impressed with their service. Online shopping for shoes can be difficult, but the brand’s policy on complimentary shipping and returns softens the blow. 

Reviewers of the Tommasso found that the shoe beat their expectations for its sleek profile. 

Most reviewers will tell you to stick to M.Gemi’s sizing guide (my experience is the same). Don’t try to “game” the system by getting a size larger or smaller than your standard size.

The Verdict

The M.Gemi Tommasso is all about versatility, which is one of the strongest reasons to get a double monk strap shoe.

The Tommasso is simple and made with premium quality materials. It’s comfortable and the rubber insert and heel lend plenty of durability. 

If you want to pick up a shoe for your everyday work attire, this checks all the right boxes. But I like it even better paired with a casual outfit. 

It may seem bold if you’re the type who’d rather blend in with a pair of sneakers, but I encourage you to try the Tommasso with a cuffed chino or pair of dark denim jeans.

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M.Gemi Tommasso
(Get $50 off your first order with code FIRST50)

Italian all the way through: the Tommasso from M.Gemi is made with all full-grain Italian leather and has the classic, low-profile Blake stitching that gives it an iconic European style.

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2. Beckett Simonon Leonard

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Beckett Simonon makes their shoes to order. It’ll take a few months for your new monk straps to show up, but what you get is worth the wait. 

If you’re in the market for a more formal single monk strap shoe, the Leonard is our favorite. Because of their lengthy made to order process, they have virtually zero extra stock, which ends up saving you a solid $100 or so.

What We Like

  • The brand makes their shoes with exquisite Argentinian full grain leather.

  • They’re built on a proprietary last that has a slim and unique silhouette—especially in the toe box.

  • Beckett Simonon does easy-to-resole Blake stitching like M.Gemi.

What We Don’t Like

  • If you buy in July, you won’t see these beauties until October. There’s about a three month period in between ordering and your shoes arriving.

What Other Reviewers Say

Nearly 20 reviewers on the Beckett Simonon site reviewed the Leonard.

Beckett Simonon Leonard Review

Only one person mentioned the lengthy wait time, but all they said was that it was “well worth” it. 

It’s a unique business model, but the reviews speak for themselves. With perfect scores across the board, reviewers mention multiple times that the quality far outweighs the price.

The Verdict

If you can handle a three month wait for your new monk straps, the Leonard is worth looking into. 

My experience with Beckett Simonon has been great (I have the Douglas Jodhpur, made on the same last)—the leather is buttery-soft and the shape is modern and masculine. 

Double monk strap shoes are far more common, so if you’d like to push the style boundaries a little, check out the Leonard.

Beckett Simonon Leonard

Beckett Simonon's signature last has a sleek, modern profile, and the Argentinian full-grain leather feels like butter.

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3. Johnston & Murphy Conard

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Johnston & Murphy helped spread the gospel of Goodyear welting to a new generation, and we’re grateful for that. 

Their brogue patterns are ornate without going overboard. And I can attest to how long these shoes hold up. I’ve owned a pair of Johnston & Murphy’s for almost seven years now, and haven’t needed to resole them either. 

If the double monk strap buckles aren’t enough flair for you and a little broguing detail gets you all excited, you can’t go wrong with the Conard.

What We Like

  • The hand-burnished Italian calfskin leather breaks in beautifully and develops a rich patina. 

  • A Goodyear welt means easy resoling and a bit of extra water resistance. 

  • Johnston & Murphy adds extra cushion in the insole, and because of that, Conards are great shoes for wearing all day at work. 

What We Don’t Like

  • The Conard has a rubber outsole, but with no grip-pattern. The added traction is one of the major benefits of a rubber sole, so it’s curious that Johnston & Murphy wouldn’t take advantage of that. 

What Other Reviewers Say

Over 100 reviewers give the Conard a nearly perfect score:

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It’s amazing to read through and see how many of the reviews come from repeat customers. Some say this is their second pair of Johnston & Murphy, others say the Conard is their fifth pair. 

The brand has decades of experience, and their loyal fan base proves they’re doing something right.

The Verdict

High quality leather shoes under $200 can be hard to find. Johnston & Murphy was my first introduction to better quality shoes, and I still have my Reynolds after seven years. 

If you’re not sure you want to go “all-in” with a pair of monk straps over $200, but you still want something that will be worth the investment, these are my top choice (provided you like the broguing detail).

Johnston & Murphy Conard Monk Strap

Johnston & Murphy is a legacy American brand, and they've been a big player in reintroducing the US to the quality of Goodyear welted shoes. Comfort is their main concern, but the style isn't too shabby either.

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4. Alden for J.Crew Monk Strap

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Need a pair of monk strap shoes that stand out? Look no further than Alden.

Their single monk strap shoe designed for J.Crew is a masterpiece, albeit on the pricey side. 

The pebbled calfskin upper is some of the best quality you can find in a shoe and Alden has a legacy of craftsmanship and refinement.

What We Like

  • The full glove leather lining is silky soft and a pleasure to wear. 

  • The pebbled calfskin upper looks rich and breaks in smoothly so the shoes only look better with time.

  • USA-made, and there are a few Alden shops around the country you can have these repaired at. 

What We Don’t Like

  • The dark brown alpine grain colorway is the only option available. I would’ve liked to see black for a more formal option, too. 

What Other Reviewers Say

There aren’t many crowdsourced reviews on Alden, but there are entire forums devoted to the brand. 

Alden is a well-known classic American shoemaker, and they’ve built a base of ardent fans.

The Verdict

If you’re ready to take the plunge and pick up a luxe pair of monk strap shoes, Alden is the first place you should look. 

While we love the design done for J.Crew, you may also want to check and see if there’s an Alden shop near you. Their staff is very knowledgeable and they have a variety of constructions that can help with flat-feet, plantar fasciitis, and other foot-issues. You can even customize some parts, like the laces and soles. 

But if you’re not nearby an Alden shop and you want your luxe monk straps now, head over to J.Crew and get these beauties while you can.

Alden Monk Strap for J.Crew

If you're satisfied with nothing but the best of the best, check out Alden's pebbled leather, Goodyear welted, single monk straps.

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5. ALDO Adlershof

Aldo aldershof monk strap shoe

I have mixed feelings on ALDO—they make great looking shoes. But they’re usually uncomfortable and don’t last very long. 

Truthfully, I think it’s better to save up and get a pair of M.Gemi, Beckett Simonon, or Johnston & Murphy shoes.

But if your budget can absolutely not exceed $100, then the Adlershof is worth looking into.

What We Like

  • The Adlershof is a sleek-looking shoe with classic brown and black colorways.

  • ALDO often runs massive sales, so you can find these under $60 sometimes. 

  • A square toe box is unique and adds some distinction to the style.

What We Don’t Like

  • I haven’t tried the Adlershof, but I’ve had two other pairs of ALDO shoes and the leather wasn’t great.

  • The cemented sole construction means that once the sole wears out, the shoe is done for. 

What Other Reviewers Say

After wading through a few dozen reviews, most customers have the same sentiment as I do.

These are solid shoes if you’re on a tight budget and you want something to wear once or twice a week.

If you plan on wearing them every day, you can expect them to last about six months. If you give them some rest, they can last a year or more.

The Verdict

ALDO doesn’t make the best quality shoe, but they look good and the brand runs deep sales that make shoes like the Adlershof seem pretty attractive. 

Don’t get these shoes if you need something for your everyday work wardrobe. They won’t last long enough to justify the cost. But if you want something stylish and cheap for those one or two outfits that would pop with a crisp-looking double monk strap shoe, the Adlershof is worth a shot.

ALDO Adlershof

ALDO makes good looking shoes. The quality isn't amazing, but if you want a double monk strap shoe under $100, wait for one of ALDO's many deep-cut sales and pick up a pair.

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How to Wear Double Monk Strap Shoes

Double monk strap shoes are becoming more and more popular as guys are catching on to this whole fashion thing (you’re here, so you’re on the forefront). 

While many folks still relegate double monk strap shoes to the dress-shoe world or the workwear universe, they don’t need to be.

Part of what makes this style of shoe so wonderful is their versatility. I love to wear double monk straps casually. A rolled up pair of chinos, tucked in t-shirt, and sockless look is my favorite combo. 

MGemi Monk Strap Shoes 5

It’s simple, but the cuffed pants and tucked in shirt make it more thoughtful. If you have a beautiful pair of shoes like the M.Gemi Tommasso, this outfit lets them be the star of the ensemble. 

Of course, double monk straps look dapper and can be dressed up too.

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If the “investment banker” look isn’t your style and you want something a little more relaxed, choose a brown pair of double monk strap shoes and explore some navy pairings

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It’s not all business though, and there’s an excellent middle ground between totally casual and formal. 

Pair suede double monks with a light linen suit and a henley or t-shirt underneath for an Italian summer vibe. 

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As you can see, to only wear double monk strap shoes to work is to leave out half of their appeal. Try pairing them with jeans for a date night and see how much they elevate your look. 

The History of Monk Strap Shoes

Monk strap shoes originated in Europe, but they’re gaining popularity in the US. 

The name comes from the strapped sandal worn by European monks years ago—though I’m guessing the holy men weren’t in it for the fashion. 

Over time, the sandal was adapted into a close-toed shoe and the monk strap as we know it was born. 

For some, the hardware is a bit flashy, though the style is becoming more common in workplaces. Fashion-forward gents are flocking to monk strap shoes because of their versatility. Yes, they’ll make do in the office, but you can really turn heads when monks are paired up in a casual outfit. 

Most monk strap shoes have a cap toe, though this is changing every day with more brogue, plain toe, and boot styles coming out everyday. 

Strap In

With the thousands of different options out on the market, I hope we narrowed down the field enough for you to find your new favorite shoes. 

My favorite double monk strap shoe—balancing cost, quality, construction, comfort, and style—is the M.Gemi Tommasso.

Discount Available
M.Gemi Tommasso
(Get $50 off your first order with code FIRST50)

Italian all the way through: the Tommasso from M.Gemi is made with all full-grain Italian leather and has the classic, low-profile Blake stitching that gives it an iconic European style.

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

If I were in the market for a single monk strap shoe, I’d endure the wait and choose Beckett Simonon’s Leonard

If I had a little extra padding in my wallet, first I would take a bath in cognac, but afterward I’d buy the Alden single monk strap from J.Crew. And if I accidentally overspent on cognac for my bath and only had $80 left, I’d stick with ALDO

So which monk strap shoes speak to you?


Can you wear monk strap shoes with a tuxedo?

Yes. We recommend a high polish black shoe, and a single monk strap is better than a double monk strap for a tuxedo occasion, though that’s not strictly necessary.

Are monk strap shoes formal?

Monk strap shoes can be formal, but they don’t need to be. They’re very versatile shoes, meaning you can pair them with a crisp pair of blue jeans for an elevated casual look, or pair them with a suit for a formal wedding. For formal events, remember the darker and more polished, the better.

Why are they called monk strap shoes?

European monks wore strapped sandals, and eventually the fashion world drew inspiration from the look. Monks never wore these types of stylish shoes, but the name stuck.

Can I wear monk strap shoes with jeans?

Yes, absolutely. Monk strap shoes look excellent with jeans as an elevated casual ensemble. Try cuffing your jeans once or twice and show a little ankle for a more relaxed, but still dapper look.

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