11 Shoes Every Man Should Own

by Jamie Wilson

Reviewed & updated: October 19, 2022 by Jamie Wilson BA

Whether you’re an avid footwear collector or just starting to put together your essential pieces, our extensive guide on all things shoe related will give you the best idea about what shoes you actually need in your life. From boots to brogues to trainers, a modern man needs all the essentials.


Shoes have an interesting history. From functional to flashy designs, it can be easy to feel lost in all the details. As a whole, footwear choice is extensive. A simple wander through a history museum will show you how shoes have evolved through centuries dating back to Ancient civilisations. Now, we look at today’ men’s shoes, and there are endless styles to choose from.


Different types of shoes can amp up more simple outfits, or create clean, minimal lines for a more sophisticated look. Colours no longer stop at the neutral palette, and you’ll find that vivid prints are available too. No matter what your personal style’s like, there are pairs out there that will match everything you love.

The Best Oxford Shoes Guide You'll Ever Read

Oxford Shoe

Oxford Shoes are often confused with Derby Shoes, but there are marked differences between the two. Here’s the easiest way to tell them apart: closed or open laces. To put it briefly, you’ll see a line of stitches underneath the vamp for an Oxford versus more space and no stitched line with a Derby.

When it comes to styling, the Oxford shoe is much more formal than the Derby. These are the ones you see being paired with tuxedos, and more often than not you’ll come across the shiny patent ones. You might not feel you really need a pair, but it doesn’t hurt to invest in a decent set of Oxfords. There will be occasions where you need to break out a tux – weddings and holiday galas come up quick and before you know it you’ll need a shiny smart pair of Oxfords.

Origins of... The Derby

Derby Shoe

The Derby shoe on the other hand, can be worn with the rest of your suits. The open space on the vamp feels slightly less formal, but there’s still a clean, minimal design to the Derby shoe that you get with the Oxford. Good for date nights and semi-formal events, the Derby is a huge favourite and a forever a classic among men’s shoes. These are still smart so you need to keep them clean and well polished – the care is everything.


With their unmistakable perforations, brogues have a broader range than the Oxford or Derby. Being shoes that can go beyond the casual direction, they’re great paired with sports jackets and button down shirts. They’re definitely suitable office shoes for men but you can also wear them for a trip to the pub on a Friday night.

You don’t have to stick to tradition. Many designers and brands are creating soles out of lightweight foam and cork for an extra summer casual look. Surprisingly durable, these styles could become your weekend favourite in no time. Both a pair of jeans and chino’s work well with this kind of shoes, keep the legs slim and not too skinny and complete the look with a button down shirt on it’s own or open over a T-shirt.


Loafers, depending on the material, can come off dressy or very casual. Going for a nice neutral leather will help you compromise between the two. Easy to slip on and off with a moccasin-like construction, the loafer has quite a bit of history behind it. There isn’t an exact starting point on its origins, but it comes down to either Norway or England. Regardless of which version is correct, this leisurely design came about in 1920s Europe. Fast forward a little and G.H. Bass & Co introduced their Penny Loafer in the 1930s. Widely accepted and appreciated for having no laces and an easy design, their loafer is still very much loved today.

Monk Straps

Monk shoes fall in-between your Derby and Oxford shoes. Named for historically being worn by monks, Monk shoes remain one of the best shoes for men. From single to double straps, you can even find them in brogue patterns and styles. Though they need to find a proper place between being for formal or casual situations, styled right they can fit both occasions.

If you need to pair them with a suit, stick to black and brown – it’s sleek and has no strings to deal with. The monk strap shoe also looks seamless with well hemmed trousers and a shirt. This is definitely an ultra stylish men’s shoe, but if you want a pair that fits your denim days, try them in different coloured leather and suede. As time progresses, designers get more adventurous. You can find monk shoes in royal blue, green, and several shades of red and oxblood – we’ve even seen a few on the avant-garde side. Wear your bottoms cuffed and try printed socks if you want to be more daring.

Chelsea Boots

Some of the best casual shoes for men include a reliable pair of Chelsea boots. A huge proponent of the Mod era of the 60s, these boots date back to Queen Victoria. Slim fitting at the ankles with an elastic panel to create a smooth look that was loved by the musicians of the Swinging London scene. Even now, they’re still considered as one of the top cool shoes for men.

During the youthful revolution of the 60s in Britain, Chelsea boots were often seen paired with tailored suits. Since they’re slim around the ankle, wider leg styles with your boots won’t do anything for the boots or your shape. Skinnier legs help show them off. With endless outfit possibilities, try them with your button downs, vintage-fit sweaters and even your most beaten-up pair of jeans.

Sneakers And Trainers

Streetwear followers are always on top of the newest drop, whether it’s the next Nike Air Max or a collaboration to beat all other collaborations, sneakers are constantly flying off store shelves. Trainers and sneakers will undoubtedly provide solid comfort, but it’s the ease of making them coordinate to nearly all your clothes that’s key. You can’t beat a pair of trainers as being the ultimate cool men’s shoes.

Trainers are a big part of the modern guys life – there’s so many styles, colours and variations that have made the trainer world massive. Sneakerheads create massive hypes over the newest and latest trainers, making the reselling market bigger and better each year.

Running Shoes

There’s many die-hard runners out there, and running shoes are heavily reviewed. Yes, they can have sharp, edgy looks, but function is the most important thing. If you’re a distance runner, they need to efficiently support your weight when you walk and run to reduce the pressure on your knees. Without superior arch support, there’s loss of stability. Cushioning needs to respond properly and not have an overly tight-fitting toe box. So there’s really a lot to think about.

We know there’s camps for Nike being the best or New Balance being on top, but in reality you need to make sure they work for your foot shape, width and length. You want them to be light so you can move fast but keep in mind that if you run on pavement, dirt trails or a professional track, these things need to be taken into account when looking at running shoes.

Boat Shoes

White rubber soles on men’s boat shoes are originally meant to provide traction on slippery boat decks, they’re now considered a part of men’s daily wardrobes. This is an ultra casual shoe for weekend gatherings and family summer events, especially when paired with pieces equally as summery. When you feel like you just want to run around in a V-neck T-shirt and shorts, grab your boat shoes or cuff some trousers and wear a button down with the summery shoe.

One major issue you’ll run into with boat shoes is the super stiff leather. Breaking them in will happen with wear over time, but if you want to speed up the process then get them wet. We know some of you are thinking “leather and water?!” Don’t worry, there are proper ways of breaking in leather with water.

  • With your boat shoes on, step into your basin or even the bathtub with a few inches of lukewarm water.
  • Move and flex your feet, this will help the leather conform as the water soaks in. You’ll start to see how the leather shapes around your foot.
  • Step out, and soak excess water with a towel. Then if you have them, use shoe trees placed inside as the leather dries. If you can, just wear them as they dry for a true fit.
  • The easiest thing to do is to wear them out on the water or beach, get them wet and they’ll dry as your day goes on.


When you think about plimsolls and trainers they can sometimes seem the same. You see a canvas upper and a rubber sole, but the difference is a matter of terminology. In the UK, plimsolls still stand as how they have been throughout their history. They’re always referred to as a shoe made with those features.

However, in other parts the world, especially the United States, plimsolls have been categorised with the rest of the sneakers. This includes leather sneakers, running shoes and so on. Sneakers is such a broad term over there compared to how the plimsoll still stands alone here. Sticking to tradition, style your plimsolls with shorts and T-shirts, roll up the sleeves of your shirt and wear it open. Distressed denim will always work with plimsolls. Cuff up your pants, throw on a light jacket and you’re set for a Saturday.

Desert/Chukka Boots

Many shoe styles come from military backgrounds, and the Chukka boot is no different. Worn during World War II across Libya and Egypt, these boots were made to survive extremely harsh desert conditions and terrain. Like many of the men’s stylish shoes we examined, Chukka boots transitioned from a life built for function to now purely being a fashion necessity.

The sole ranges from its original rubber construction to leather, and the upper comes in a variety of skins and colour variations. A minimal design that works amazingly with tailored trousers or a sports coat to jeans and casual shirt. A go-to for inside and outside the office, you can make these nice shoes for men work in almost every situation.

The Top 11 Men’s Shoes

  • Wear a pair of Oxford, Derby or Brogue shoes when going for a more formal look.
  • Loafers are great for a smarter casual style. Try wearing them with a sports jacket.
  • Chelsea and desert boots are great for smart casual looks.
  • Trainers and plimsolls are the ultimate comfortable and casual footwear.

On That Note

There are a whole host of shoes that are forgotten about when choosing what to wear. Whether you need to be smart for a night out or Sunday lunch or you’re after something more casual to run to the shops in, you should have footwear that fits accordingly. If not, these are the top pieces that need a definite place in the wardrobe.

Feature image from Pinterest

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