Fashion legend Christian Dior said that “you can never take too much care over the choice of your shoes”. This still holds true today. Whatever the outfit, whatever the occasion, the perfect pair of men’s shoes is the key to completing your look. Here, we break down the top tips for buying new kicks in 2023 plus our most-loved brands and styles.
In This Men’s Shoes Article…
How to Buy Men’s Shoes Online:
What’s the Occassion?
The most important questions to ask yourself before buying a new pair of men’s shoes are these:
- Why am I buying these shoes?
- What sort of events and activities will I use these shoes for?
These might seem obvious, but they’re more important to ask when buying shoes than any other garment. Sneakers don’t look good at weddings, Brogues aren’t great for marathons, and so on.
By answering these questions, you’ll immediately be able to prioritise certain factors when buying your new shoes – do they need to be lightweight? A certain colour – black, white, brown? Do they need to be made of a certain material? You catch my drift.
Start with what you’ll be wearing them for and work back from there to ensure you buy the right pair for purpose.
What’s In Fashion Right Now?
It’s important to understand that some men’s shoes are absolutely timeless. A white sneaker, a black brogue or oxford, and certain brands like Vans, classic Converse, or Nikes will never go out of style.
As such, it’s well worth stocking your wardrobe with a few of these classics that you can wear again and again, knowing they’ll style with near enough anything.
Having said that, shoes aren’t exempt from the endlessly cresting and crashing waves of fashion trends: loafers, derbies, apron-toed oxfords and suede chukka boots are all expected to sweep the streets in 2023.
So on top of your must-have capsule wardrobe shoes – those pairs that never go out of rotation – be sure to top up your collection with a couple of pairs that really show you’ve got your finger on the pulse this season.
Whether that be a bold colour, a daring print, or an interesting design that sets it – and you – apart from the crowd, be as subtle or as audacious as you like.
Sizing and Fit
Sizing is more crucial with men’s shoes than it is with any other garment; badly fitting shoes won’t just hurt your aesthetic, but they could do you some serious damage as well.
Sizing can vary slightly by brand, so always err on the side of caution (if in doubt, go up).
If you don’t already know your size, it’s best to go and get measured up in your local store and try out a few different pairs.
Here are our tips for getting the perfect fit:
- Have a 1/4 to a 1/2 inch of space between your toes and the end of the shoe.
- Take them for a short test drive – just lap the store a few times – you won’t truly know the fit just by standing still.
- Get your feet measured in the afternoon – your feet expand during the day.
- Watch out for internal labels or inseams that could rub against your feet on longer outings.
- And… this one may seem obvious: If one foot is bigger than the other, make sure you buy the size that fits the larger foot.
Materials and Durability
Materials are important in men’s shoes for a few reasons.
First, they’re important for getting your look right dependent on the event. For weddings or other smart occasions, dark leather is what you want. For summer BBQs or smart-casual events, suede or lighter leather could provide a nice middle ground. For running, you want performance-engineered composites.
When looking at running or workout sneakers, the material is also important in terms of weight: if you’re trying to run 10k, you don’t want to feel like you’ve got a ball and chain on your ankle.
In contrast, if all you’re doing is trotting around a garden party or office, this is far less of a concern.
Sustainability is also an increasingly important factor for customers and designers alike. If sustainability is important to you, avoid plastics and composites; chase those natural materials instead.
Some materials are also more durable than others, meaning your shoes may (or may not…) last longer. This is often reflected in the pricepoint but always check the material information online before purchase.
Short For Time? These Are Our Top Picks
| Best Sustainable Men’s Shoe: | VEJA |
| Best Vegan Men’s Shoe: | TOMS |
| Best Skate Shoe: | Vans |
| Best All-White Men’s Shoe: | Oliver Cabell |
| Best Basketball Shoe: | Converse |
| Best Running Shoe: | On Running |
| Best Smart-Casual: | Johnston & Murphy |
| Best for Wide Feet: | Grenson |
Cariuma
1/22Price: From $79
Sizes: 5-13
Material: Cotton
Customer Reviews: “Comfortable well designed shoes built to last with no compromise. I like the unique style. Good value for the price.”
Co-founders David and Fernando started Cariuma after feeling that major sneaker companies were producing uncomfortable sneakers that weren’t created in a sustainable or socially responsible way. They set out to provide stylish, comfy, consciously made shoes, and let us tell you, Cariuma shoes certainly meet those goals.
Cariuma’s cool men’s sneakers come in a huge variety of styles and colours that’ll keep your footwear game cool as ice.
Tropicfeel
2/22Price: From $159
Sizes: 6-12.5
Material: Recycled nylon, recycled elastane
Customer Reviews: “So far so good. I am not use to give reviews so quickly. Shoes truly waterproof, easy clean, easy to step in. had to change from higher to low shoes for problem easily to step in.”
Created to fill a gap of versatility present within the men’s sneaker market, Tropicfeel is dedicated to creating travel gear that is lightweight and sustainable, and above all can be worn for almost any and every situation or adventure.
Tropicfeel has a huge selection of cool shoes for men, available in awesome colour combinations. If you tend to travel or spend a lot of time in the great outdoors and you’re after a cool pair of sneakers that’ll meet your comfort needs as well as fashion needs, Tropicfeel is the brand for you.
Allbirds
3/22Price: From $105
Sizes: 8-14
Material: Merino wool, FSC-certified TENCEL™ Lyocell
Customer Reviews: “Super comfortable, light-weight shoe at a great price! Plus: they’re machine washable! I’ve washed mine twice already and they still look and feel great. Highly recommend!”
New Zealand-American company, Allbirds is dedicated to creating eco-friendly footwear made from sustainable resources, but that doesn’t mean that Allbirds’ sneakers don’t deliver in the comfort or style department.
Allbirds have high and low top sneakers as well as slip-on style shoes all available in a variety of cool and fresh colours. If you’re after a pair of cool shoes for men that’ll keep your feet comfortable while also serving street-style looks, you can’t go wrong with Allbirds.
Why we like them? Not the world’s coolest shoes but they are comfy.
Casca
4/22Price: From $168
Sizes: 7-15
Material: 100% Vegan materials
Customer Reviews: “The shoes have a phenomenal appearance. Get lots of compliments. But the real kick are the custom insoles. It takes it from a vanity purchase to a plain out smart one. Worth the price and then some.”
In most cases, ‘cool’ and ‘comfortable’ don’t usually go together; especially in a fashionable sense. But Casca merges the two together easily. All of Casca’s footwear is designed with orthotic experts and are constructed with a triple-thick cushioning with Everest-grade rubber, to ensure premium comfort and long wearability.
But Casca’s range of shoes do NOT look like the kind of daggy orthopedic shoes you see on the elderly. Casca’s shoes are extremely modern and stylish, and will most definitely add a cool look to any outfit you pair them with.
Oliver Cabell
5/22Price: From $219
Sizes: 6-15
Material: Leather
Customer Reviews: “Absolutely love these. Just got them in and I love the color and design. Gives you a classic sneaker look but also will have people wondering what they are. You’ll definitely stand out.”
Oliver Cabell is committed to fair pricing for top quality and design, and strongly advocates against unethical manufacturing and inflating prices. The result? Hand-crafted, European-made, and affordable premium shoes that are designed to last.
The best bit is that most of Oliver Cabell’s sneakers feature an extremely cool stitched circle design on the side; reminiscent of Golden Goose’s style but at a much more affordable price point.
Everlane
6/22Price: From $65
Sizes: 5-13
Material: Reconstituted leather
Customer Reviews: “The shoes came in yesterday and they are beautiful and feel like they are made with very durable material. High quality shoes.”
Everlane prides itself on exclusively partnering with ethical factories and using only the finest materials for their products; they call it “Radical Transparency”. Therefore, you get quality garments, footwear, and accessories that will last for years to come, with an added bonus of feeling good about supporting a company that strongly advocates for fair wages and working conditions.
Everlane’s Court Sneaker is crafted with full-grain leather and sports a contemporary utility style. Available in four colours, Everlane Court Sneaker is a must-have when it comes to cool shoes for men.
Cole Haan
7/22Price: From $150
Sizes: 7-13
Material: Leather
Customer Reviews: “Great fit, look stylish, very comfortable, super lite weight! I wish they were not lace ups and had the fake lace up look so one could treat them as loafers. overall, very pleased.”
Founded in 1928, in Chicago, Cole Haan is an American brand renowned for its footwear which is both aesthetically-pleasing and functional. Cole Haan employs various technologies when crafting its footwear, to ensure ultimate comfort, most notably the Zerogrand, and Original Grand collections.
Cole Haan’s aesthetic is extremely unique; they put their own subtle twist on popular and classic footwear styles. If it’s cool shoes you’re after, you have to check out Cole Haan’s range, as his shoes will most definitely make you stand out in a crowd.
Why we like them? Unique shoes and well priced for the man about town.
Johnston & Murphy
8/22Price: From $129
Sizes: 8-14
Material: Leather
Customer Reviews: “Very comfortable and sharp looking!”
Founded in 1850, Johnston & Murphy first specialised in crafting quality and highly durable work shoes but in 1880, took the craftsmanship and durability of their work shoes and built them into a line of higher-fashion footwear, which quickly became popular around the world.
Johnston & Murphy’s footwear range includes dress shoes, sneakers, boots, running shoes, etc. – but the thing that unites them is their unmistakable sophistication. Johnston & Murphy have perfected blending the elegance of dress shoes with their more casual styles, meaning any pair of Johnston & Murphy shoes will keep you looking cool and polished no matter where you wear them.
Von-röutte
9/22Price: From $156
Sizes: 35-46
Material: Leather
Customer Reviews: “Have 4 pairs of different styles. Older they get the better they get. Like me. Love this company, their quality and service.”
Australian brand, Von-röutte are renowned for their timeless sneakers that are made to last. Bringing an experimental flair to minimalist sneakers with pops of colour and modern detailing, the brand’s main inspiration comes from three simple Nordic values: to be simple, functional, and beautiful.
If you’re after cool shoes for men to add to your collection, Von-röutte has an abundance of styles that’ll all fit the bill.
Why we like them? The coolest shoes made down under.
Aurelien
10/22Price: From $311
Sizes: 40-45
Material: 100% French calfskin
Customer Reviews: “This product is looking so beautiful. And then shape and design are look like to me. This quality so beautiful. This product smooth and soft. Wear the shoe and walking look very attractive style. I will refer the product to another person.”
Dutch brand, Aurelien operates out of Italy, and initially placed its focus on shoes for men (although the brand has since expanded to a full-range luxury clothing store). Trying to recreate the image of Mediterranean gentlemen strolling along the coast on a summer evening, Aurelien’s range of shoes perfectly combine cool and elegance to create shoes that’ll elevate your wardrobe without overdressing you.
With everything from boat shoes to sneakers, all crafted in luxurious suede and available in both classic and playful colours, Aurelien is definitely a brand to consider when on the hunt for cool shoes for men.
Why we like them? Trendy designs.
Converse
11/22Price: From $60
Sizes: 3-13
Material: Cotton
Customer Reviews: “Classic, perfect Chucks even after owning a zillion pairs in diverse colors! Sweet!”
A brand that really doesn’t need an introduction is Converse. Known for their Chuck Taylor All Stars, Converse has stood the test of time for a reason; their shoes are simply cool. You really can’t go wrong with the classic white featuring a blue and red stripe around the sole, but when Converse has every print, colour, and style available, go with what you think is cool; because isn’t confidence in your own tastes and styles really the coolest thing of all?
Why we like them? Classic and super cool.
Grenson
12/22Price: From $270
Sizes: 6-12
Material: Leather
Customer Reviews: “Their shoes are comfortable, the leather is good quality, they’re generous with the sizes especially if you’re wide footed.”
Founded in 1866, Grenson has been continuously making durable and high-quality shoes. All of Grenson’s shoes are ‘Goodyear Welted’ – a shoemaking technique, meaning the shoes are extremely strong and will last you for a very long time. But don’t think that Grenson compromises on style, as their huge range of men’s footwear is extremely fashionable.
With everything from loafers to sneakers, dress shoes to boots, Grenson has every type of shoe you could possibly want to add to your wardrobe. If you’re after cool shoes for men that won’t fall apart after a few wears, Grenson is the perfect brand for you.
Vans
13/22Price: From $75
Sizes: 6.5-14.5
Material: Cotton
Customer Reviews: “Its a great pair of shoes, i always find it cool looking down at my feel when i wear them and the amout of compliments people give me is crazy, 10/10 would buy again!”
One of the most recognised brands around the world, and not just in the skateboarding industry, Vans has become a dominant player thanks to its Old Skool shoe, which is immensely popular for its versatile cool style.
Vans have every colour and print of shoe available, meaning whatever you think will spice up your wardrobe, they’ll have it.
Nike
14/22Price: From $65
Sizes: 6-15
Material: Synthetic leather
Customer Reviews: “These sneaks are good for running, dodging, driving, and overall conquering the world. Basically every activity besides sleeping.”
Nike is another brand that doesn’t really need an introduction as it’s one of the best sportswear brands in the world. Deeply committed to creating groundbreaking sport innovations, Nike dares to design the future of sport with its highly functional (yet also aesthetically pleasing) products.
Chances are you’ve seen many people sporting Nike’s Air Force 1 sneakers but that’s because the shoe is ridiculously cool. The fashion staple features clean lines, a strong midsole, and is available in both classic and fun colourways in low, mid, and high-top styles.
Orlebar Brown
15/22Price: From $225
Sizes: 7-12
Material: Mixed textiles
Customer Reviews: “Love these so comfy and lightweight took them to Las Vegas washed when back amazing.”
Founded in 2007, London-based brand Orlebar Brown initially focused on ‘shorts you can swim in’; tailored swim shorts that can be worn on the beach or in the pool but are also smart enough to then be worn to summer dinners and drinks.
However, over the years the brand has evolved to a full resort collection inspired by 1960s poolside utopia; think the Riviera or Palm Beach. The result is clothing, footwear, and accessories that are sophisticated yet fun. Orlebar Brown’s cool shoes for men just exude holiday style and will make you look cool and relaxed.
Why we like them? Just cool looking shoes with a twist.
VEJA
16/22Price: From $146
Sizes: 40-46
Material: Leather
Customer Reviews: “I have two Veja sneakers pairs and I can say that they are 100% worth it. They’re comfortable, great quality, sustainable, and trendy.”
VEJA, founded in 2004, is dedicated to producing environmentally-friendly sneakers, made with raw materials sourced from organic farming and ecological agriculture, without chemicals or polluting processes. Completely transparent about their entire process, VEJA has a great range of sneakers that are not only sustainable but extremely stylish.
VEJA takes the classic white sneaker style and injects it with fun pops of colour with the result being seriously cool shoes for men that’ll keep your feet comfortable in eco-friendly style.
Kenneth Cole
17/22Price: From $55
Sizes: 7-13
Material: Leather
Customer Reviews: “Great shoes very comfortable very happy with them.”
Founded in 1982, Kenneth Cole is now one of the most recognised fashion companies in the world. Dedicated to producing high-quality clothing, footwear, and accessories, Kenneth Cole’s products are not only well-made but are also extremely stylish.
Kenneth Cole’s cool shoes for men are inspired by the modern needs of the urban man and feature versatile sophisticated aesthetics, premium materials, and comfort technology. With every style of shoe available – slides, sandals, sneakers, dress shoes, boots, etc. – you really can’t go wrong with adding a pair of Kenneth Cole shoes to your closet.
TOMS
18/22Price: From $55
Sizes: 7-14
Material: 100% Vegan materials
Customer Reviews: “Comfortable and got a few compliments on them. Definitely matches chill fall vibes, when ya break out the flannel and hot toddies.”
Founded in 2006, TOMS’ main goal is to improve lives. Therefore, it’s no surprise that the brand is extremely sustainable and ethical. Currently, TOMS gives one third of their profits in support of grassroots efforts, including organizations that are helping communities thrive—creating change at the local level and driving progress from the ground up.
TOMS has a huge range of men’s shoes that are all made with sustainable materials but don’t you dare think these shoes don’t deliver on style. TOMS’ shoes are extremely cool and are available in a wide variety of styles and colours.
Yatay
19/22Price: From $350
Sizes: 35-46
Material: Bio-based materials
Customer Reviews: “Must say that I am a sneaker freak and in love with these shoes! Perfect fit, lightweight, and super comfortable. Great quality, and eco friendly. Perfection!”
A relatively new brand, Yatay was launched in 2018, and it aimed to merge the best Made-in-Italy quality with the most advanced green fashion technology to create timeless, comfortable, and sustainable sneakers. Environmentally conscious and with a green soul, the mission of Yatay is to prove that uncompromised quality can be achieved without sacrificing sustainability.
Their awesome range of sneakers are crafted with vegan leather that’s much more breathable than normal leather and prevents sweaty feet. Extremely comfortable, you’ll be the King of cool rocking these eco-friendly sneakers.
Rag & Bone
20/22Price: From $260
Sizes: 41-46
Material: Recycled Polyester
Customer Reviews: “Truly the most comfortable sneaker. … Retro, is right. … Love these shoes and their classic look. They’re quite comfortable too.”
Everything Rag & Bone designs is made to last as well as both original and timeless. Committed to doing things “the right way, not the easy way” Rag & Bone’s products are extremely high in both quality and style.
Rag & Bone’s range of shoes are unique in style, and while they may not be to everyone’s tastes, the original and fresh aesthetics Rag & Bone have to offer are definitely cool.
TAFT
21/22Price: From $225
Sizes: 6-15
Material: Raw wool
Customer Reviews: “I am more than pleased with these shoes. I have found many outfits to wear them with and the feedback I get is great! I will definitely purchase more from Taft.”
Founded in 2014, TAFT is a men’s footwear brand specialising in unique, bold shoe designs. TAFT shoes are produced in Spain and Portugal with premium textiles ranging from suiting wool, to woven upholstery fabric, to Charles F. Stead leather. Meticulous in their work, intentional in their designs, and obsessive over what makes the cut, TAFT has become renowned for their extremely well-made unique men’s shoes.
With boots, dress shoes, loafers, and sneakers on offer, what sets TAFT apart from other brands is their daring and bold fabric choices. Their shoes can be had in traditional colours, but also in playful prints that are nothing short of cool. If you want cool shoes for men, you have to take a look at TAFT’s awesome collection.
On Running
22/22Price: From $160
Sizes: 7-14
Material: Recycled Polyester
Customer Reviews: “I have tried on numerous pairs of ON’s and haven’t found one comfortable enough for long shifts on the floor. Until now. Secure fit, comfortable, sustainable, and cute. Win-win.”
Swiss brand, On Running was founded in 2010 to revolutionise running by producing shoes that are comfortable, well-made, and improve the running experience.
On Running doesn’t just cater to runners though; they have a huge range of lightweight all-day wear shoes engineered for high performance and complete comfort. Available in a few different styles and colours, On Running’s shoes have a rather unique look to them which make them seriously cool.
Why we like them? Funky vibes from an athletic shoe.
