A few years back, I took a trip to Italy.
My goal was to bring back three things:
- A bottle of Tuscan wine
- A collection of ravioli stamps
- 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.
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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.
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.
Both single and double monk strap shoes will pair well with jeans, or try rolled chinos for some European panache.
5 Best Men’s Monk Strap Shoes
Best Double Monk Strap: Beckett Simonon Hoyt
Beckett Simonon crafts their shoes to order, and there are some pros and cons to consider with that. Their quality is phenomenal, and the full grain Argentinian leather feels like a dream.
All of my Beckett Simonon’s have been comfortable right out of the box, so I have no complaints there.
The big issue is that your shoes can take several weeks (or even months) to arrive because they’re hand made to order.
If you need a double monk right now, you’re better off elsewhere.
But if you want a high-class shoe that feels like a $400 piece, but costs half that, the Beckett Simonon Hoyt is the way to go. You should also check out their suede options while you’re there.
What I 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 I Don’t Like
It can take several weeks, or even months to arrive, though Beckett Simonon is very good about communicating with you through the entire wait.
What Other Reviewers Say
Beckett Simonon is beloved by professional reviewers and casual wearers alike. The general sentiment on this brand is: sure, it’s inconvenient to wait a few weeks to get your shoes, but they fit and feel like an absolute dream when you get them.
The Verdict
The Beckett Simonon Hoyt is all about versatility, which is one of the strongest reasons to get a double monk strap shoe.
The Hoyt 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 Hoyt with a cuffed chino or pair of dark denim jeans.
The Beckett Simonon Hoyt is the best blend of quality, value, and style we've found with a double monk strap shoe. The only downside? There's a waiting period as they're handmade to order. Quality-wise, these shoes should be in the $400 range, but they're much less expensive than that.
Best Brogue Double Monk: Johnston & Murphy Reece
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 Reece.
What I 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, the Reece are great shoes for wearing all day at work.
What I Don’t Like
The Reece 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 Reece a nearly perfect score:
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 Reece 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 $300 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 $300, but you still want something that will be worth the investment, these are my top choice (provided you like the broguing detail).
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.
Most Unique Double Monk: Taft Prince
Want a pair of brown monk straps that stand out? Look no further than Taft.
Their double monk strap shoe has a wacky design with opposing buckles, but it still looks classy.
Taft makes their shoes with the best quality materials (this leather is tanned in England and feels creamy-smooth).
What I Like
The full glove lining is silky soft and a pleasure to wear.
The French calfskin upper looks rich and breaks in smoothly so these shoes only look better with age.
These feature a Goodyear welt so they’re able to be resole if needed.
What I Don’t Like
There aren’t many color options and black isn’t on the menu.
What Other Reviewers Say
A lot of folks come to Taft for their boots, and several reviewers mentioned they’re becoming Taft shoe converts. It’s always a positive sign when you see people coming back and purchasing a second pair from a brand.
The Verdict
If you’re ready to take the plunge and pick up a unique pair of double monks, Taft is the first place you should look.
Taft’s design is a bit quirky, but not too outlandish. The end result is a stunning funky double monk that’s still at home in the boardroom.
The Prince from Taft is one of the more unique double monk strap shoes I've seen. Instead of both upper straps facing the same direction, they're pointed opposing each other. It's a classic Taft move where they subvert expectations but still look classy.
Best Single Monk Strap: Beckett Simonon Leonard
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. Plus, you can get the Leonard in black leather, too.
What I 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 I 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.
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's signature last has a sleek, modern profile, and the Argentinian full-grain leather feels like butter.
Best Budget Monk Strap: Cole Haan Johnson
The Cole Haan Johnson is the lowest price double monk strap shoe I can recommend, as below this level, the quality and comfort really suffer.
Truthfully, I think it’s better to save up and get a pair of Beckett Simonon or Johnston & Murphy shoes.
But if your budget can absolutely not exceed $125, then the subtle gold buckles of the Cole Haan Johnson is worth looking into.
What I Like
What I Don’t Like
The Verdict
Cole Haan makes a good looking shoe. At just over $100, it's a budget friendly option, though I'd wait to find it on sale or pony up for one of the Beckett Simonon shoes above.
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.
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 Beckett Simonon Hoyt, this outfit lets them be the star of the ensemble.
Of course, double monk straps look dapper and can be dressed up too.
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.
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.
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 15th century 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.
Why Are They Called Monk Strap Shoes?
Before there were laces, 15th century European monks were using leather straps and brass buckles to keep their shoes on their feet. Modern day dress shoes took the look as inspiration and classed it up for what is now known as an office favorite.
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.
There are some high end double monk strap makers like Vince Camuto and Paul Evans, but through the research, Beckett Simonon seems to offer similar quality for a much lower price.
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 Beckett Simonon Hoyt.
The Beckett Simonon Hoyt is the best blend of quality, value, and style we've found with a double monk strap shoe. The only downside? There's a waiting period as they're handmade to order. Quality-wise, these shoes should be in the $400 range, but they're much less expensive than that.
If I were in the market for a single monk strap shoe, I’d endure the wait and choose Beckett Simonon’s Leonard.
If you’re all about the comfort, check out the Johnston & Murphy Reece.
So which monk strap shoes speak to you?
FAQs
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.
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.
