The Very 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 shoe that a man can add to his wardrobe.

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

However, when wearing monk shoes, there are a few ‘rules’ you should adhere to:

  • Of all the dress shoes, monk shoes are still considered slightly more casual.  Therefore, if you plan on wearing a tuxedo, then you will be better off going with Oxford or Derby shoes instead.
  • Monk shoes pair incredibly well with sport jackets, blazers.  In addition, they are a nice addition to any sophisticated smart casual look.
  • Single or Double strap monks are both considered to be fashionable.  However, three monk straps are more of a trendy option that will likely go away in a few years time (hence their absence from this article).
  • You can wear monk shoes with or without socks.

Here are some of the finest crafted single and double monk shoes that you can purchase with a few clicks of a mouse (listed in alphabetical order):

Best Single and Double Monk Strap Shoes For Men

1. 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.

2. 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 shoe making, 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 shoe makers.

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.

3. Magnanni Marco Monk Strap Loafer

Plain colored dress shoes are nice, but having a textured color to your leather shoes is even nicer, and that is exactly what Magnanni has done with their Marco strap loafers.

These dress shoes feature a very elegant color without being plain or boring.

The tasteful stitching on the sides and around the buckle further improve the design, and create a very aesthetically pleasing piece of footwear that is a joy to wear.

The handsome silver buckle is equally functional and stylish, and pulls the shoe together very nicely. These shoes go well with most pant and suit combinations.

Magnanni Marco shoes are made with 100% leather, which definitely accounts for a fair chunk of their price.

In terms of fit, these shoes have an elongated toe, and a higher heel and ankle piece that may or may not cause some problems depending on the fit.

They do run a little large as well, so purchasing the next half-size down should result in a closer fit. These shoes come in a wide range of sizes, from a 7.5 to a 15, meaning there is a fit for every man.

The biggest complaint with these shoes is that breaking them in is a little tough, and may take several weeks. Wearing with thicker socks will make this process faster, but they still do need plenty of time to stretch.

4. Cole Haan Men’s Williams II Monk Strap Loafer

If you are looking for an elegantly simple dress shoe, the Cole Haan Williams II is an ideal first choice for men looking for their next comfortable dress shoe.

This shoe features a plain leather upper with a rubber sole and a single monk strap that spans across the upper part of the foot. This strap allows for easy tightening or loosening of the shoe to accommodate all different foot shapes and sizes.

The buckle is also highly fashionable, and the removal of the laces makes this shoe very easy to put on and take off.

Because this shoe is entirely made of leather, it is exceptionally easy to break in. The leather interior contains the foot, and adjusts as necessary while you wear them.

These shoes fit true to size, and many buyers agree that these shoes are extraordinarily comfortable with a deep rich color that is striking against many different colors of pants.

Both shoes feature a mid-high arch and a matte finish that is subtle when worn but looks as good as a shiny finish. The leather insole is perhaps not the most comfortable, but supplying your own insoles will make breaking in these classy shoes so much easier.

5. Magnanni Men’s Cotillas II Double Monk Strap Shoes

Made with 100% leather, including the uppers and the sole, and are perfectly designed for everyday life; whether you want to wear them casually or you want to wear them to an event, these shoes are perfect for any occasion.

According to buyers, these shoes are great in all aspects: style, comfort, and functionality.

There aren’t too many negative complaints about the shoe as a whole, but a couple of individuals have expressed some concern around the hard leather exterior.

These shoes are a bit difficult to break-in and require plenty of time to get them where you need them to be. Other than the first few wears, after you get these shoes broken in, they are a dream to wear around and are incredibly stylish to boot.

They are a bit expensive, but that’s the price you pay for designer quality. These shoes are only available in medium width, and because they are already rather narrow shoes, they would not be good for people with wide feet.

6. Massimo Mateo Double Monk Cap Toe

Seamless design with a handsome finish, that 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.

7. Stacy Adams Men’s Dinsmore Monk Strap Slip-On Loafer

Stacy Adams is a reputable company that specializes in men’s dress and casual shoes for every day of the year.

They showcase extraordinary quality with timeless design that is a pleasure to wear day after day.

The Dinsmore monk strap dress shoe is not only a great quality shoe, it also looks and feels like a dress shoe should; it is comfortable, stylish, and works well with many different outfits.

The shoe upper is made of 100% leather, which allows it to stretch and mold to your foot over time, without warping or losing it’s shape.

What stands out the most with this shoe is the superb color each shoe has. Not only are the leather uppers made with bold, quality leather, but the synthetic soles are also colored to offer a striking contrast between the two parts of this shoe.

Because of this, every Dinsmore shoe can be worn with a wider array of pants and suits. These shoes come in 5 different colors, such as black, red, and even navy. It also comes in many sizes, starting from a US 7 to a US 15, with many half sizes available, as well as a choice between medium and wide widths.

For men who have issues finding their size, these may be a good place to start.

About Shawn Burns

Shawn Burns is the founder and senior editor of Tools of Men. He started this site with the goal of teaching men proper grooming habits and sensible style. Shawn's expertise includes in-depth product reviews and how-to articles. Shawn was recently featured in the Wall Street Journal for his expertise.

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