A contemporary shoe with heritage appeal, the monk strap shoe is one of the sempiternal dress shoe styles of all time, remaining within the collective consciousness of the sartorially-minded since their inception. Classy yet fashionable, monk strap shoes can be slipped on and off and are ideal for the lace-averse gentleman. A viable alternative to Oxfords and derby shoes, the meticulously crafted nature of monk strap shoes lend the style a sense of formality, while the straps themselves add a touch of rakish insouciance to any outfit.
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History of monk strap shoes
Although the monk strap shoe as we know it today is a relatively new development, the inspiration behind them dates back centuries. Monks are a rather atypical source of stylistic stimuli, but fortunately it’s their footwear and not their number #1 haircut or hooded robe we’re looking to emulate. During the 15th century, the life of a European monk primarily comprised worship and manual labour. For monks located in alpine regions, the latter component required a more protective style of footwear than the sandals the religious sect is often associated with. The result was a closed-toe iteration of the single or double strapped sandals, forming the basis of what we now know as monk strap shoes.
During the next couple of centuries, monk strap shoes found their way into public wardrobes, flitting in and out of style as lace-up shoes grew in popularity. Monk strap shoes underwent a couple of stylistic changes and made their way back into the public eye during the 20th century, however, it wasn’t until the early to mid-2000s that the style solidified itself as a mainstay in the fashion world. Today, monk straps have completely shunned their manual labour origins, firmly cementing their place as a sophisticated dress shoe.
What are monk strap shoes?
Almost an amalgam of Oxfords and loafers, monk straps are a laceless leather slip-on that retains the vamp and tongue of its lace-up relatives. Forgoing laces, monk strap shoes feature their namesake straps across the vamp, fastened with a buckle or two. Double monk strap shoes are the most popular style, however, single-strapped versions also have their place. If you’re in the mood for something particularly daring, there are also the rare triple-strapped iterations. Additionally, monk strap shoes for men can come with wing-tips, toe caps, or brogue detailing, while a pair of monk strap boots makes for a unique way to differentiate yourself from the crowd.
Single monk strap vs double monk strap
A seemingly innocent question, albeit one that has served as fodder for ongoing debates within the sartorial world. Single monk straps have a sleek, streamlined silhouette, making them a suitably understated footwear choice for smart casual, business, and formal dressing. Meanwhile, double monk strap shoes allow for a little more expression of personal style, imbuing any outfit with a playful note and making them ideal for parties, weddings, and other get-togethers. Though historically considered too casual for office wear, when styled appropriately double monk straps can fit in well within a corporate setting.
How to wear monk strap shoes
A key drawing card of the monk strap shoe is its ability to seamlessly move between dress codes and occasion wear. Whether it be an upscale luncheon or Friday afternoon knock-offs, the monk strap shoes are equally at home. From casual to formal attire, here’s how to style them.
Casual
For casual attire, double monk strap shoes are your best bet. When dressing down, avoid patented iterations and dark hues in favour of relaxed materials like suede or brushed leather and lighter or more vibrant shades. Style double monk strap shoes with slim fitting trousers, chinos, or jeans and a button-down shirt or t-shirt. For warmer weather dressing, opt for shoes in a lighter shade like tan and pair them with linen pants and a lightweight knit polo shirt.
Smart casual
Smart casual outfits are where monk strap shoes really hit their stride. A pair of brown leather shoes works well for most occasions, whether it be teamed with an open-necked button-down shirt and pleated trousers for drinks, or paired with slim-fitting trousers, an Oxford shirt, and a blazer for work.
Business formal
Both single and double strap iterations can lend themselves to business formal wear. If opting for the latter, stick to dark, neutral tones like black and chestnut brown. Stick to well-tailored, elevated pieces like suits or suiting separates, sleek shirting or roll neck jumpers, structured outerwear, and accoutrements like ties, pocket squares, and tie clips to ensure your outfit sits firmly in business casual territory.
Formal
Swapping out your Oxford or derby shoes for a pair of monk straps makes for the ideal way to infuse your formal outfits with a personal touch. While single straps are traditionally recommended for formal wear, double strap iterations can also work when done well. Deep hues like black and chestnut brown always work well, however, more interesting shades like oxblood, burgundy, deep blue, and even forest green make for a savvy sartorial statement. A three-piece suit in grey or black teamed with black patent leather monk strap shoes is a foolproof option, while a beige or tan double-breasted suit works well with burgundy, oxblood, and forest green footwear. Alternatively, switch it up by teaming a plain charcoal or black pinstripe suit with a sleek pair of black leather monk strap boots.
The best monk strap shoes to buy
From understated single straps to boot versions, these are the best styles on the market.
1. Tom Ford Black Leather Monk Strap Boots


If you’re going to go all out with a pair of monk strap boots, let them be Tom Ford. Impossibly sleek and elegant, these boots are as at home peeking out from under a slim-cut suit as they are teamed with jeans. The clean, streamlined silhouette and gold hardware make them elevated enough for formal wear, while the high cut and double straps give them a touch of rocker edginess.
2. Santoni Leather-Trimmed Suede Monk-Strap Shoes


Ideal for casual and smart casual wear, these Santoni monk straps pair monk straps with the moc toe stitching typically found on loafers. Pair with a knit polo and pleated linen pants for the ultimate summer outfit. ‘
3. Mr P. Peter Leather Monk-Strap Shoes


This iteration from Mr P. is as simple as it gets. Crafted from smooth leather and featuring silver hardware and an unembellished vamp and toe box area, these shoes are ideal for business formal dressing.
4. Carmina Plain Toe Monk Strap Shoes


For a dressy style in a unique shade, look no further than this pair from Spanish shoemaker Carmina. The single strap and minimal hardware are ideal for formal dressing; pair with a three-piece suit or slim-cut trousers and a blazer worn over a finely-knit turtleneck.
5. Zette Shoes Archer Men’s Vegan Leather Boot


A low-cut boot with a single monk strap detail, this pair from Zette Shoes is cut from vegan-friendly Spanish leather. With an elasticised upper side panel, it’s suitable for both business formal and casual occasions.
6. Stefan Cooke Biker Buckle-Detail Monk Shoes


While we’re not sure actually monks of yesteryear would approve of this Stefan Cooke, it’s an undeniable way to stand out from the crowd. With oversized buckles around the upper and heel quarter, it’s the perfect way to lend jeans, chinos, or trousers a tougher edge.
7. AQ By Aquila Dwayne Tan Monk Strap Shoes


A style that shifts between relaxed and smart casual occasions, these double monks add interest through a cap toe and brogue detailing. The dark tan shade lends itself to being paired with suiting separates in lighter shades and everyday attire like pleated trousers and chinos.
8. Santoni Double Buckle Monk Shoes


Double monks with a clean silhouette, the burgundy hues of this pair adds interest to both business formal and formal attire.
9. Reiss Suede Monk Strap Shoes


Lend a pop of colour to your casual outfits with these airforce blue double monks.
Words by T. Angel