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Men’s Shoe Style Guide

Men’s Shoe Style Guide

Men’s shoe styles can vary widely, so it’s good to have a knowledge and understanding of the different options available. Some types of men's shoes are more suitable for certain occasions than others, so take a look at our guide to make sure you make smart footwear choices.

Boat & Deck Shoes

Men's Casual Shoes

Casual shoes form part of every man’s wardrobe, and whatever your personal style is we bet you have at least one of these types in your style staples. Apparently the average man owns 12 pairs of shoes – a good balance of both smart and casual shoes in your collection will ensure you have the right footwear for any occasion.

Men’s Boat Shoe

Boat & Deck Shoes

Boat shoes, probably more commonly known as deck shoes made a massive resurgence into popular men’s footwear trends a few years ago. In the 1980s in particular, deck shoes were hugely popular with ‘preppy’ style and were mentioned in a publication of “The Official Preppy Handbook” by Lisa Birnbach in 1980.

Before the ‘invention’ of boat shoes, sailors and boatmen struggled to keep their grip on slippery boat decks, hence the need for a sturdy sole with good grip.

Early in the 1930’s, a passionate boater named Paul Sperry was noticing that he needed far more grip when he was on out and about on his boat. Apparently, he first noticed a solution to his problem when he took his dog, Prince, out for a walk on frozen Connecticut ground. He noticed that Prince was slipping less on the ice and he devised a shoe to emulate the grip that Prince had; Sperry’s new shoe design had a sole with herringbone cuts and grooves.

In 1935, Sperry introduced white soled deck shoes as black soled shoes left marks and dirt on the deck of the boat. He sold his Sperry Top Sider shoe to the US Rubber Company and the US Navy who started to sell the shoes on a mass scale.

Boat/deck shoes traditionally have two or three eyelets, are crafted from mid to dark brown leather – although in recent years, you may notice them in any colour. Historically they are made out of leather, but again, more recently, negating practically for style, they are now sold in canvas or fabric, even suede.

Men’s Trainers


Advances in technology and manufacturing have allowed the design and development of highly complex technical running shoes that fall into their own category outside of just simply ‘men's trainers’. High performance running shoes can be a real investment and can provide safety as well as style when training. Fashion trainers are also a comfortable, casual shoe that can be worn at any time, whether exercising or simply relaxing.

Men’s Canvas Shoes

Canvas Shoes

Men’s canvas shoes predominately came into fashion in the 80’s, when skate shoes became increasingly more popular.

Before this period, canvas shoes were usually associated with plimsolls, which were worn for sports and usually before adulthood. Plimsolls probably evoke some nostalgia in everyone, as they were compulsory for P.E. lessons at school. Canvas plimsolls have their own names in many different regions and cultures, and were usually black with an elasticated front panel and a thick rubber sole.

Fashion has come a long way since then, and although plimsolls are still available for kids for their P.E. lessons, canvas shoes for adults are now much more comfortable and stylish.

Canvas shoes can come in almost every pattern and colour imaginable. Canvas is a versatile and lightweight fabric that is perfect for everyday wear.

Men’s Sandals / Flip Flops

Sandals/Flip Flops

Men’s sandals divide opinion more than any other type of footwear. They are the thin line between practical and utter style sin, the men’s sandal may have a reputation but if you wear it with some rules in mind, there’s no need to shy away from it.

  • Less is more: The less straps the better, according to fashion experts, around three straps is perfect.
  • Get a pedicure: If you’re going to brave bare feet, get a pedicure to make sure they’re in tip top condition.
  • Turn up: Turn up or hem trousers before wearing sandals. It will stop trousers getting caught under your sandals and add a contemporary twist to your outfit.
  • The obvious: No socks with sandals. Ever.
  • Outfit choices: If you’re going to wear a risky choice such as sandals, keep the rest of your outfit sharp, sophisticated and classic. Think tailored linen shorts and a shirt.
Men’s Espadrilles


Nothing says ‘Summer’ like a pair of espadrilles. The shoes originate from Spain, and are defined by their braided rope soles. ‘Esparto’ is the plant that was burnt and twisted into thick, durable rope to form early styles of espadrilles.

The shoes have humble origins and were typically worn by soldiers and priests in the early 19th Century- a far cry from the high end, luxury versions being designed by top Fashion houses these days.

The shoes are lightweight and allow your feet to breathe, making them the perfect summery style essential.

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Men’s Dress Shoes

Men’s Dress Shoes

Every man should own a great pair of dress shoes, even if you only wear them once in awhile, a classic pair is well worth investing in.

When it comes to dress shoes, even the tiniest details can alter the name of the shoe and it can be tricky to navigate what shoe is called what. Whether you’re trying to understand the basics so you can pick the right shoe for a wedding, or if you’re trying to make sure you’ve covered all your bases, our men's shoe types guide breaks down the most common men’s dress shoe styles.

Men’s Brogues


Men's brogues are often mistaken as a style of shoe in itself, whereas the term brogue actually refers to the pattern of the perforation made in the shoe. A Derby shoe or an Oxford shoe can have "brogueing". The perforations were originally made to let out water in wet terrain yet have now become solely a decorative addition to a shoe.

There are several styles of brogueing:

  • Full Brogues: With brogueing on the entire shoes and wingtips
  • Semi Brogues: Brogueing is seen on only half the shoe
  • Quarter Brogues: Brogueing is feature on only the end of the shoe
  • Longwing Brogues: Brogueing is featured down the shoe lengthwise rather than horizontally across the shoe

Brogues are a classic men’s shoe choice, having held their place in the history of men’s shoes for decades.

Men’s Oxfords


The Oxford is by far the most classic of dress shoes that you will come across, instantly recognisable and the best starting point if you’re looking for a wardrobe staple. Also one of the most versatile of shoes that can be worn in any situation or with any combination of casual or formal wear. The name Oxfords originates from Oxford students opting for this style of shoe over the Oxonians that were the preferred choice in the 1800’s.

There are several variations on the Oxford, but whatever variation you choose, a pair of black or brown Oxfords is a classic that you can’t go wrong with, whilst for dress or more formal wear, a pair of patent Oxfords will finish your outfit with an extra dash of sophistication.

The Oxford shoe can come in 4 different styles:

  • The Cap Toe Oxford
  • The Wingtip Oxford
  • The Plain Toe Oxford
  • The Whole Cut / One Piece Oxford
Men’s Derbys


The difference between a Derby and an Oxford is very slight and often Derbys are, understandably, confused with Oxfords.

The difference in the shoes lies at the ‘top’ of the shoe. The Derby shoe has stitching on the vamp, right across the shoe, whereas the Oxford has its tabs sewn under the front panels. The type of shape allows for a wider fit, making the shoe more practical, comfortable and more suitable for everyday wear.

There are again several variations on the style of shoes:

  • The Cap Toe Derby
  • The Wingtip Derby
  • The Plain Toe Derby

Monk-Strapped Shoes

A quirkier option for formal wear featuring similar shaped shoe without the laces. Unsurprisingly the Monk strap takes its name from the styles Monks originally wore. Monk style straps are thick straps across the front of the shoe, usually buckled up with either one or two buckles depending on the amount of straps.

This is a style not for the faint hearted and will almost certainly be the focal point of your entire ensemble.

Men’s Loafers


King George VI used to wear loafers as casual house slippers and men's loafers were popularized in the 1930s after being mass produced in the states. The shoe was kept as a casual shoe until the 60’s when businessmen started wearing leather loafers with suits.

Loafers feature a wide strap at the front, although they slip on, and are usually decorated with either a bit strap, a tassel or kept plain – the plain variations are called penny loafers.



Shopping can a stressful and uncomfortable experience, but once you’ve clued yourself up on what style of shoe is what, you can ask for helpful advice from shop assistant’s using the right terminology, or search online for exactly what you want without too much hunting around. All you have to figure out now is what size you need and how to style your shoes… good luck!

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