A Comprehensive Guide To Smart & Formal Men’s Shoes

Do you know your men’s Oxford shoes from your Derbies? How about the difference between chukka boots and desert boots or what shoes to wear with a suit? Discover everything you need to know about types of shoes here.

Men’s Brogues

Back in the day when they were first popularised, men’s brogues were considered a less formal smart shoe to be worn in the countryside rather than town but these days they’re considered one of the smarter options available. Like many terms in menswear, the word ‘brogues’ can be misleading because it doesn’t refer to a particular classification or style of smart men’s shoes like Oxfords or Derbies. Rather, men’s brogues refer to a particular feature: decorative patterned perforations in the uppers of the shoes, or ‘broguing’ to use the specific terminology. In the case of wingtip brogues, the broguing appears on almost the entirety of the shoe and resembles, you guess it, a bird’s wing. For that reason, men’s brogues can technically also be Oxfords or Derbies (or even boots come to think of it). 

What shoes should you wear with a suit? What style of shoes are considered formal? The world of men’s shoes can be a confusing one, and with so many styles and variations, it can be tricky to figure out the answer to these sartorial questions. Without a guide like this one, that is. Read on to find out more about what types of shoes you should wear for certain occasions and how to spot men’s smart shoes in the wild.  

Men’s Oxford Shoes 

Without a doubt, the smartest men’s suit shoes are widely considered to be men’s Oxford shoes – they’re usually what people have in mind when they say men’s dress shoes or men’s formal shoes. With origins in the nineteenth century – when they were once known as Balmorals before taking on the moniker of Oxford University – they are characterised by a closed lacing system with no gaps or spaces in the uppers (unlike Derby shoes). The minimalistic construction means men’s Oxfords shoes are a lot sleeker than others, with a refined silhouette suited to more formal clothing such as black tie or business suits. There are several variations on Oxfords, depending on what look you’re going for. Cap-toe Oxford shoes, for example, are common, with stitching across the toe area, while whole-cut men’s Oxfords are made from one single piece of leather with no seams save the one at the very back of the heel.

Men’s Derby Shoes 

The main thing distinguishing men’s Oxford shoes from men’s Derby shoes (or ‘Derbies’) is the lacing system: while it’s closed on Oxford shoes, it’s open on their Derby equivalent, with separate vamp and quarters (parts of the upper), leaving a gap between the vamp and laces. This creates a slightly less formal silhouette. In recent years, chunkier soled Derby shoes have emerged lending them more fashion-forward appeal, but if you opt for classic low-profile soles, you’ll find it’s still an incredibly classic and versatile shoe, especially for work or weddings. If you’ve ever asked the question, ‘what formal shoes can I wear for most occasions?’ then men’s Derby shoes are probably your best bet. 

Men’s Loafers

Did you know men’s loafers were originally designed as indoor-only men’s shoes? It wasn’t long, however, that people realised that these comfortable and smart shoes deserved their moment in the sun. Characterised by their slip-on design and lack of laces, men’s loafers are most typically made from leather or suede and come in a few variations. The most classic is the penny loafer, which has a slotted strip across the upper – menswear lore has it that it was once used to store coins, hence the name. Then there’s the tassel loafer and its more ostentatious cousin, the kiltie loafer, which includes fringing. Whatever you pick, the men’s loafer has cemented its place as one of the most versatile men’s designer shoes around.

Men’s Monk Strap Shoes 

Men’s monk strap shoes are a much rarer sight than other entries on this list, but they are on par on a smartness scale with men’s Oxfords, Derby shoes and brogues and therefore are considered formal enough for work as well as special occasions like weddings. Men’s monk strap shoes (sometimes referred to as simply ‘monk shoes’) are so-called because they resemble the sorts of styles worn by monks back in the day and are defined by buckled straps which are used to fasten the shoe rather than laces. As men’s designer shoes go, they’re an elegant choice that’ll set you apart from the crowd.

Men’s Chelsea Boots

Are boots considered formal footwear? Well, the answer to this question largely depends on your definition of ‘formal’. For a traditional black tie dress code, men’s boots, for the most part, wouldn’t make the cut. But men’s boots can almost certainly be smart. If you’re looking for a pair of men’s boots to go with a suit, for example, then you won’t go wrong with a pair of polished men’s Chelsea boots. Dating to the Victorian era, men’s Chelsea boots evolved out of traditional riding boots and by the 1960s they’d earned their current name thanks to the popularity of the area in London with the young and well-heeled ‘mods’ of the era. Usually made from leather (or suede), Chelsea boots are characterised by an elasticated insert that offers a comfortable fit and negates the need for laces.

Men’s Desert Boots 

There’s some confusion about the difference between men’s desert boots and chukka boots (see below) – but there’s really only one key variation you need to keep in mind: men’s desert boots are equipped with a crepe rubber sole. Usually made of suede or nubuck, desert boots were worn by troops in Burma as a hard-wearing but comfortable footwear option for decades before Nathan Clark popularised them in Britain in the 1950s. While men’s desert boots might not be suitable for very formal occasions or more conservative offices, they’re still an excellent alternative for smarter looks especially in autumn and spring.

Men’s Chukka Boots 

Men’s chukka boots have a lot in common with desert boots, but unlike desert boots, men’s chukka boots are defined by a more solid, traditional sole. This has the advantage of making them altogether a bit smarter. And while we tend to think of chukka boots as classically suede or nubuck (like their cousin the desert boot), they look especially sophisticated in polished leather, too.

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Words: Molly Isabella Smith