How to wear monk strap shoes

Monk shoes from Samuel Windsor are sleek, stylish and brimming with personality

Monk shoes are sleek, stylish and brimming with personality
Image: Samuel Windsor

Your monk shoes look sharpest when you wear them with smart pants, a crisp shirt and cashmere sweater. It’s a classic look that’s perfect for almost every social occasion. To dress things up a little, or for an evening out, add a tweed jacket.

Monk shoes are a versatile addition to your menswear wardrobe, working just as well with a sharp suit as for weekend brunches at your favorite cafe. Wear single or double monk straps to create a look that’s sleek, stylish, and just that little bit different.

What are monk strap shoes?

Single strap monk shoes from Samuel Windsor

Monk strap shoes can often be slipped on like a loafer
Image: Single strap monk shoes from Samuel Windsor

As the name suggests, monk shoes are descended from medieval monks who first introduced a strap-fastened shoe to provide more comfort and protection than their usual sandals.

Modern monk shoes are often smart dress shoes featuring a side fastening consisting of either one or two buckles. But they’re occasionally used to add an unexpected dash of flamboyance, and so you’ll also find funky two-tone, patterned and leopard print versions under the guise of men’s goth or punk creepers.

Single or double monk straps?

Double strap monk shoes in oxblood from Samuel Windsor

Patent leather double-buckle monks are incredibly smart
Image: Double strap monk shoes in oxblood from Samuel Windsor

There’s some debate about whether single or double monk straps are smartest. Some argue the more minimalist single buckle creates a cleaner silhouette that’s more suitable for formal occasions, while others point out that with a larger piece of leather covering the opening, double monk straps are actually the sleeker of the two styles.

Our advice is to base your decision on the individual shoe – what looks to be the more formal footwear probably is, indeed, smarter. After all, whether they feature one buckle or two, patent leather monks look great with your tux.

Are monk shoes suitable for the office?

Brogued monk shoes from Samuel Windsor

Brogued monks are ideal for an approachable look
Image: Brogued monk shoes from Samuel Windsor

Yes, you can wear monk shoes to the office – a pair of single or double strap monk shoes offers a very acceptable alternative to your usual Oxfords. Wear yours with your navy or charcoal suits, and if you feel like adding a unique touch to your office ensemble, try oxblood monks – a very tasteful way to rock monk straps!

For tan or rustic tweed suits, brown monk shoes are a better choice than black. Brogued monks look great with tweeds, and because this combo adds approachability, it’s a look that’s a great choice for people-facing professionals like teachers, college lecturers and therapists.

Smart casual monk straps 

The less shiny the Samuel Windsor monk shoe, the less formal it is

The less shiny the shoe, the less formal it appears
Image: Monk shoes from Samuel Windsor

Think of monk straps as a sturdier version of a loafer. They’re almost a slip-on, but not quite. What you’d normally wear with your loafers is equally suitable for a switch to monk shoes – think chinos, cotton shirt and a thin sweater. Or go preppy by wearing a button-down shirt and cardigan, or a tweed sports jacket for fall and winter seasons.

Alternatively, choose a pair of pants in a textured fabric like tweed, corduroy or moleskin, and top with a shirt, knitted tie, and smooth twill jacket for contrast. Our tip – keep a twill jacket ready for cool blustery days – twill packs a high thread count which results in a fabric that offers more than token wind resistance.

Casual monk shoes

Double strap monk shoes in tan leather from Samuel Windsor

This casual tan coloured leather is great with jeans
Image: Double strap monk shoes in tan leather from Samuel Windsor

Wear a pair of brown monk shoes with with tan cords, a burgundy fisherman’s sweater and a wax jacket and flat cap. It’s a look that gives more than a nod to the kind of wardrobe typical of English countrymen. Add a soft, brushed cotton tattersall shirt for a touch of British comfort.

Feel like kicking back and relaxing? Go for black or oxblood monk straps with indigo or black jeans. Add a pair of classic sunglasses and you’re ready to unwind.

Monk shoes make an excellent addition to your wardrobe. Extremely versatile – you can wear them with your tux, your business suit, your smart casual ensemble, and even your casual weekend gear. Whatever the occasion, there’s a monk strap to suit.

Posted in Men's Shoes.

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