The Best Single and Double Monk Strap Shoes

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Both single and double monk strap shoes are considered by many fashion experts to be one of the most versatile and best dress shoes that a man can add to his wardrobe.

Their sophisticated yet restrained design gives these shoes a truly unique look compared to any other dress shoe.

Here are some of the best monk shoes currently available.

1. Best Double Monk Strap: Allen Edmonds ‘St. Johns’ Double Monk Strap Shoe

Allen Edmonds 'St. Johns' Double Monk Strap Shoe

When it comes to formal American footwear, there is none better than Wisconsin-based Allen Edmonds.  Founded in 1922, Allen Edmonds makes finely crafted shoes with high-quality materials.  The St. Johns Double Monk Strap shoes are no exception.  

A leather upper paired with a rubber sole, these double monk strap shoes are elegant and timeless in style.  The cap-toe, along with some light broguing, delivers an extra touch of class and sophistication.  

Available in many sizes, widths, and three different colors, it makes it easy for any man to find a pair that they can slide into.

If you are looking for the quintessential double monk strap shoe, it doesn’t get any better than the St. Johns by Allen Edmonds.

2. Best Monk Boots: George Cleverley Tan Monk Boots

George Cleverley Tan Monk Boots

These British-made monk strap boots by George Cleverley are a luxury splurge for men who want uncompromising style.  Featuring a tan pebble-grain leather that has been paired with gold-tone fastenings, the style is timeless and will be an upgrade to any weekend or semi-formal wear.  

The bottom of these monk boots has been outfitted with premium Dainite rubber soles for added confidence with each step.

3. Smart Selection: Paul Evans The Poitier Double Monk Strap Shoe

Paul Evans The Poitier Double Monk Strap Shoe

The Poitier Double Monk Strap Shoe by Paul Evans is a well-made and stylish selection.  For starters, the handpainted colors of Oxblood, Marrone, Havana Brown, and more subtly demonstrate a unique palette that offers a modern but not an overly trendy look.

But what sets this shoe apart from others on the market is its craftsmanship.  Relying on a full-grain leather upper, it’s both durable and will develop a lovely patina with time.  Additionally, the sole features blake stitching, allowing it to be resoled by your local cobbler, greatly extending the life of the shoes.

The plain toe increases versatility so that you can get good use out of The Poitier on multiple outings.  

Those unfamiliar with Paul Evans should know that they started in 2012, are headquartered in New York, and make their shoes in Italy.

4. Affordable: Cole Haan Wagner Grand Monk Strap Dress Shoe

Elegant and sophisticated, this Cole Haan product is just what you need if you are looking for a plain dress shoe to wear every day.

The Wagner model features a double monk strap; the straps are connected by one wide strap that expands across the arch of the foot, with two buckles to secure it. This is ideal for men who want a tighter grip near the arch, and a looser one across the top, or vice versa.

There are three holes on the strap that, although they do not provide a whole lot of wiggle room, they do give you a little extra comfort right where you need it.

Cole Haan has been making shoes since 1928, so it’s no wonder that these shoes showcase exceptional quality, style, and function.

These shoes may not look like much, but they are handsome in their simplicity and will go well with numerous outfits, plain or patterned. The leather sole and upper supply comfort and flexibility, while the rubber sole adds stability and all-weather wear to this great-looking shoe.

Wear with dress pants, jeans, or slacks to dress up any outfit for an affordable price.

5. For Formal Wear: George Cleverley Thomas Leather Monk Strap Shoes

George Cleverley Thomas Leather Monk Strap Shoes

What makes for a good quality shoe?

Is the leather the manufacturer uses, or the finish after the fact?

Perhaps it is due to years and years of experience in the field that makes a shoe pleasurable to wear. The George Cleverley line of shoes is a testament to those years of professional shoemaking, and the Thomas dual monk strap shoe is just one of many shoes to catch the eye of many highly-esteemed individuals.

This shoe features a solid black finish with striking silver buckles and a cap toe that draws viewers into the rest of the shoe.

The dual monk strap is comfortable and blends seamlessly into the rest of the shoe, providing a classical look that can only be achieved with quality shoemakers.

The leather lining, soles, and uppers contribute to this shoe’s price tag, but if you are looking for a quality product, you pay for what you get. These shoes are sure to last you through many years, especially if you only wear them occasionally.

They are comfortable and make a great work shoe as well. Perfect for formal occasions, business engagements, or as part of your everyday look. Available in US sizes 7 to 13, with half sizes available.

6. Best Under $100: Massimo Mateo Double Monk Cap Toe


Seamless design with a handsome finish is what Massimo Mateo strives for.

This particular shoe of theirs features an elegant flow from toe to heel, and in its simplicity, there is beauty.

For starters, these shoes are made out of 100% leather, and the leather is capped at the toe to give a slight oxford look, without detracting from your outfit. The finish carries a slight shine, though it is not overwhelming at all.

The dual monk straps are fashionable, and they can be adjusted for greater comfort.

Both the black and the brown colors are gorgeous and will accent a suit or casual outfit nicely.

Day or night, these shoes work with whatever you want to put them through. The leather lining and the insole are both extraordinarily comfortable to wear, and you don’t have to worry about undoing and redoing laces, as these shoes are entirely slip-on.

Many customers say that this product fits true to size, but there are some outliers that say that these shoes actually fit a bit bigger than what they say. Your best bet will be to order your size and see how it feels and exercise the return policy if necessary. These Massimo shoes are available in sizes 7 to 13.

5 Tips for Buying Monk Strap Shoes

1. Number of Straps

Monk shoes will have either a single or double strap that is paired with a clasp.  Deciding on a single or double strap is a personal choice.  Some may argue that double straps are a touch more casual given the additional hardware.  However, the double strap monk shoe is the more popular of the two.

2. Upper Material

You will find that many monk shoes will vary in their leather quality.  

  • Full and top grain leather:  This is the highest quality of leather and will last you several years.  Additionally, full and top grain leather will develop a velvet-like patina with time.  Unfortunately, this leather variety may feel a bit stiff and requires a break-in period.
  • Genuine leather:  This is a cheap cut of leather that isn’t nearly as durable.  Genuine leather is often used in budget-focused monk shoes that cost under $100.  Expect a genuine leather monk shoe to only last a year or two at most.

3. Sole

If you are looking for a monk shoe that will last you for several years, it’s essential to know the stitch of the sole.  Well-made shoes will rely on a blake stitch or Goodyear welt.  Shoes featuring these stitching varieties can be brought to your local cobbler and be refreshed.  

Cheap shoes will have cemented soles (glued) that cannot be repaired.

4. Intent

Monk shoes are widely considered to be more casual compared to oxford or derby dress shoes due to the lack of laces and the addition of clasps. 

Therefore, monk shoes are best when worn with a semi-formal or smart-casual wardrobe.  

5. Price

When shopping for dress shoes, you will find price varies greatly. For example, some luxury brands, such as John Lobb, charge upwards of $3,000 for a pair of monk shoes, whereas other well-known brands such as Ted Baker charge $175.

Ultimately, set a budget ahead of time that you are comfortable with. If you want value, look for details such as the quality of the leather, sole construction, and brand reputation.