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A Gentleman’s Guide - Shoe Guide for Men

Updated: Jul 4, 2021

What’s the difference between brogues and Oxford shoes? Here’s our definitive shoe guide for men – including when to wear them and the anatomy of each style.

Owning a pair of quality handcrafted dress shoes isn’t just a luxury, it’s an integral element to every gentleman’s wardrobe.

From date night to plush traditional weddings, having the right footwear can elevate both casual and smart appearances.

This guide to men’s dress shoes will help you understand the difference between styles and identify which is best for particular occasions.

The anatomy of a dress shoe

Whether you’re wearing a pair of men’s Oxford shoes or brogues, all styles have distinctive elements that class them as a form of a dress shoe.

From front to back, a dress shoe has four parts, including the toe, vamp, facing and a quarter. Depending on the placement and construction of these four pieces will enable you to determine which style you’re dealing with.

To break this down further, we’ve included the distinctive characteristics of each below.

The Oxford shoe

A casing example of an Oxford shoe is our very own Percy Stride range (Above Percy Stride Chestnut Oxfords £250). Made popular in the 1800s, this style of dress shoe is timeless and versatile.

The most notable trait of an Oxford shoe is its closed lacing. This means that the shoe’s facing is attached beneath its vamp. As a result, the shoe hugs to the foot’s contour, making it appear sleeker.

The Oxford shoe can be dressed up or down, depending on the occasion. So, unlike other dress shoes, you’ll probably get the most wear out of a pair of these.

They work with suits, chinos and even jeans. Check out our blog 4 Outfits to wear with classic Men's Oxford shoes for more handy tips!

The Derby shoe

Similar to the Oxford shoe, the Derby is classic in design. The major difference between Oxford and Derby shoes is that the latter has its facing attached on top of the vamp – otherwise known as open lacing. This allows for a wider fit and is generally considered a more casual form of a dress shoe.

They were often worn during hunting in the 1850s, until in the 20th century, when they become a staple for a night out on the tiles.

A Derby shoe isn’t appropriate for formal suit occasions like weddings and black tie events. Instead, chinos and rolled jeans are the way forward.

The monk strap

These unique dress shoes sit somewhere in between the Derby and the Oxford in terms of formality. (Above Percy Stride Black Double-Buckle Monks £265)

Used by monks as a more protected alternative to traditional sandals, the monk strap has become a staple in a lot of wardrobes nowadays. There are no laces to think about and a good pair is extremely comfortable to wear.

There are two alternatives to the monk strap – the first with one strap and buckle and the second with two (like our Limited Edition Monks). They’re similar in shape and construction to an Oxford. However, monk strap shoes have a wide swath of leather fastened across the front of the shoe, instead of an eyelet closure.

For the best results, pair these with cuffed jeans and stylish summer suits.

It’s worth noting, if you’re looking to add a subtle touch of class to your outfit, monk strap shoes often draw attention as they’re so distinctive. Meaning they’re probably not the best choice for board room meetings.

The loafer

The original loafer was made for King George VI of England as a casual house slipper until it was popularized in the 1960s in the United States of America.

You can distinguish a loafer by its saddle – a decorative plain strap with a slit or metal ornament. Some may have tassels or a kiltie hanging from it, while the minimalist designs (like the Venetian), have an exposed vamp without any of these extra ornaments.

The signature of the loafer is the elevated seam that runs along the toe. A pair of loafers can be worn with shorts, rolled jeans and chinos for a casual vibe, or even with a summer suit.

The Chelsea and chukka boot

Both the Chelsea boot and chukka boot are ideal for smart/casual looks. The former originates from Victorian England and has rounded toes, low heels and elastic gussets on the sides.

While the latter (chukka boots), originate from polo sport and find a true balance between comfort and style. This ankle-length boot has very few eyelets for a snug fit, rounded toe, minimal stitching and open lacing (like the Derby).

In contrast to the Chelsea boot which looks better in leather, chukkas are best bought in suede.

Pair both styles of boots with jeans and chinos for a perfect date night and smart/casual look.

The brogue

Our shoe guide for men wouldn't be complete without the notorious Brogue. Its decorative pattern of perforations along the seams of the shoe, brogues make a bold statement.

This men’s dress shoe is the perfect accompaniment for Tweed blazer and jeans or crisp shirt and smart trouser combinations.

Enjoyed reading A Gentleman's guide - Shoe Guide for Men? Then subscribe to our free newsletter below. And don’t forget, you can purchase a pair of quality Oxfords or monks from our online shop today.

Or if you are looking for more guidance on what to wear with your new dress shoes try our blog Finding the right trouser length and style for your dress shoes

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