A Definitive Guide to Monk Straps
June 01, 2023

A Definitive Guide to Monk Straps

The Monk Strap Shoe

The Monk Strap Shoe is one of the most timeless footwear designs for men. Its titular straps make for a more comfortable footwear choice, and present a unique alternative to the other traditional laced dress shoes like Oxfords and Derbys. Despite the rich history of the Monk Strap shoe, it is still rarely seen compared to the iconic Oxford and Derby shoes as the former is not available off-the-rack. With their distinctive elegant look, slip-off design and versatile styling options, wearing a pair of Monk Straps will be sure to make you stand out from the crowd.


History of Monk Strap Shoes

double strapped sandals

Image Credit via Medieval Design
The origin of the Monk Strap Shoe is commonly attributed to 15th Century European monks from the Middle Ages. The monks altered their double-strapped sandals to increase their durability against the harsh conditions of the mountainous terrain and the protection offered for their feet. Out of these needs, the closed-toe Monk Strap was borne – made with efficiency and quality at the forefront. 
In the present day, the position of the Monk Strap Shoe mirrors the position of the monks in the past. While the monks did not share the high status of the noblemen for formal dress, they were also not considered part of the common folk to wear casual footwear. This middle ground in the spectrum of formality also became occupied by the Monk Straps. Today, the Monk Straps have almost entirely abandoned their physical labour roots and are now considered a proper dress shoe that is suited for both business and casual events – Not as formal as the likes of Oxfords, but not as casual as the likes of Loafers.

What is a Monk Strap Shoe?

General Construction of Monk Strap Shoes

Derby, Double Monk Strap and Loafer

A Derby, Double Monk Strap and Loafer – Image Credit via Pinterest
The Monk Strap is a strapped shoe made out of three pieces of leather. It is considered a cross between a Derby and a Loafer, sharing the Derby style of a looser and more comfortable fit (achieved by having its upper quarters overlap with the tongue of the shoe) and the slip-on wearability of a Loafer. 
Still, the most characteristic feature of the Monk Strap is the lack of lacing. Instead, laces are substituted with strap(s) and an enclosing buckle for securing the wearer’s feet. This allows the Monk Strap to function like a slip-on while retaining the tongue and vamp associated with its laced-up counterparts.

Specific Features of Monk Strap Shoes

Like all other dress shoes, the Monk Strap in its simplest form consists of the sole, upper and buckles.
blake stitch diagram1. Soles: The method by which the sole is attached to the upper is a pivotal detail that influences the durability and comfort afforded by the shoe. For instance, a blake stitched Monk Strap will typically be more durable than cemented construction (glued together). This method involves the upper being wrapped around the insole and attached between it and the outsole. A single stitch attaches everything together. This method will also allow the shoe to be resoled in the future
blake stitched double monk

    Escalada Chestnut                                               Escalada Walnut                                               Escalada Black

    Leather and Suede Monk Strap Shoes

    Leather and Suede Monk Strap Shoes – Image Credit via Pinterest


    2. Upper: Opt for real leather or suede with regard to the shoe’s material. Synthetic alternatives will look cheap and wear out faster too. 

    3. Buckles: Brass would be a good material to stick to as it is of good quality and lasts longer than cheaper alternatives.


    Types of Monk Strap Shoes


    single and double monk straps

    Single and Double Monk Strap Shoes – Image Credit via Pinterest 

    Double Monk Straps are definitely the most popular design of Monk Straps, but single- and triple-strapped versions are also available. Having said that, Monk Straps with three or more straps are typically seen as almost comical. Most will avoid these styles for they are definitely not timeless designs. Here, the old saying holds true – less is more. 


    As for the choice between single or double Monk Straps, it is a matter of personal preference.  As suggested by their name, the only difference between the single and double Monk Strap shoe is the number of straps. But, this difference translates into drastically different effects. Single Monk Strap shoes tend to be more subtle and elegant, which makes them more formal than their double-strapped counterparts. As for the Double Monk Strap shoe, which is a visibly more elaborate design, it’s more suitable for casual or business occasions. Either way, both Monk Strap shoes are versatile and unique designs that will allow you to express your sense of style.


    classic monk straps

    Gallegos Chestnut                                        Gallegos Walnut                                       Gallegos Black

    The Classic Monk Strap shoe bears striking similarity with the Oxford Wholecut in terms of style. Both shoes feature minimal details to achieve the smooth, clean cut befitting the Oxford Wholecut’s title as the most professional dress shoe of them all. 


    Cap Toe 


    Escalada Chestnut                                               Escalada Walnut                                               Escalada Black

    The Cap Toe Monk Strap, true to its name, contains a distinctive extra layer of leather stitched over the toe. The cap toe is known for adding an elegant flair to dress shoes, which is a great finishing touch to business attire.



    Wingtip Monk Straps

    Colonia Dark Chestnut                                        Colonia Walnut                                       Colonia Black

    The Wingtip Monk Strap shoe stands as a less dressy alternative to the more formal Monk Strap shoe types mentioned in this list. This Monk Strap variant gets its name from the W-shaped patch of leather stitched onto the toe (the ‘wings’) that extend across the sides of the shoe, with broguing littered throughout. 



    casual suede monk straps

    Image Credit via Pinterest 

    The Casual Monk Strap shoe has a softer image that differs greatly from the elegant and structured style of the formal Monk Strap shoes. The softer image is typically achieved by using lighter shades of leather or switching to suede construction altogether.


    How to Wear Monk Strap Shoes?


    General Guidelines

    1. On Colours: For the first pair, opt for a shade of brown for its versatility in styling. Black should only be considered if you wear a lot of charcoal and grey suits. Otherwise, consider oxblood or burgundy for the extra pop of colour. 
    2. On Socks: Have some fun experimenting by pairing your Monk Straps with striped over-the-calf socks to spice up your outfit. Wearing no socks or hidden socks works well with the Double Monk Straps in casual settings. But, for professional settings, you should either: (a) Stick with black socks when wearing black Monk Straps or (b) go with charcoal or grey socks when wearing brown and oxblood Monk Straps.
    3. When to Wear:
      1. Pairs well with casual, business casual, and less formal business attire such as blazers, tweeds, navy and grey suits. 
      2. Not suited for: Formal events (Black or White tie events, Funerals etc.) and Casual occasions (with shorts or athletic apparel).
    4. Don't slip them on! Always try to buckle and unbuckle your shoes to avoid damaging or creasing the shoe.
    5. Avoid big shiny buckles. They are easily damaged and quickly become worn out. Opt for more durable alternatives like smaller or brushed buckles instead.


    Style Advice

    Black, grey and charcoal suits with Black Monk Straps

    Black, grey and charcoal suits with Black Monk Straps – Image Credit via Pinterest

    1. Black Monk Straps: For black, grey and charcoal suits, black leather Double Monk Straps should be the only option. All other colours present a poor fit and suede will make the outfit much too informal. They are great for formal and semi-formal business occasions where a Monk Strap will be sure to set you apart from the sea of Oxford and Derbys. However, the colour is rather formal for a shoe intended for more casual occasions as well. 

     Outfits with Brown Monk Straps

    Outfits with Brown Monk Straps – Image Credit via Pinterest

    2. Brown Monk Straps: A versatile colour with light and dark shades that each offer different styling options. It can be worn to formal occasions, paired with a navy suit or blazer and dress pants. Such a combination makes the perfect look for a summer wedding. Alternatively, pairing brown Monk Straps with jeans or white chinos makes for a fun casual look.


    Outfits with Oxblood Monk Straps

    Outfits with Oxblood / Burgundy Monk Straps – Image Credit via Pinterest

    3. Oxblood / Burgundy Monk Straps: These two colours have also become increasingly popular as they pair handsomely with a navy blue suit or a pair of blue jeans.


    Monk Straps at a Glance

    The Monk Strap shoe holds a unique intermediary position between formal dress and casual wear. It offers a much-needed deviation from the classic dress shoes, while adding a touch of sophistication to casual wear. The Monk Strap’s distinctive look, comfortable and convenient design, and versatile styling options have made it the perfect shoe for men’s style expression.