9 Types Of Shoes Every Stylish Man Needs (2025)

If menswear were a ship, footwear would surely be its anchor. Great shoes do more than look the part. They underpin wardrobes, keep outfits grounded and, provided they’re carefully considered, can carry a man through the full spectrum of seasons and social occasions.

We’d like to focus on that last part here. A tightly curated capsule footwear collection should contain everything a man needs to take him from the height of summer to the darkest depths of winter, stopping at every conceivable dress code en route.

Its contents are comprised of timeless classics—versatile staples that can be mixed and matched, dressed up and dressed downad infinitum. Consider these your shoe-rack essentials—the types of shoes that no style-savvy man should ever be without.

Black Leather Oxfords

As far as the aforementioned timeless classics go, it’s difficult to imagine a shoe more deserving of the tag than the Oxford.

Black leather Oxford shoes have been the go-to formal footwear for gentlemen for centuries. They’re a loyal companion to almost any colour of tailoring, and now, with the modernisation of dress codes, there’s no reason they can’t cross over into your casual wardrobe, too.

When picking a pair, it’s a good idea to keep things simple. Opt for a toe cap if you must have detail, but avoid broguing, hits of colour or any other embellishments. The aim of the game here is simplicity, versatility and elegance.

White Minimalist Leather Sneakers

Think of these as the Yin to the black Oxford’s Yang. White minimalist sneakers are your does-it-all casual shoes. They can be paired with anything from selvedge denim and a crew-neck tee to sweat shorts and a hoodie. Splash out on a premium pair and even tailoring isn’t out of the question.

It’s hard to imagine a more versatile piece of footwear, which means they’ll be seeing plenty of action all year round. This considered, it’s well worth investing in a luxurious model from the likes of Common Projects, or even a traditional shoemaker like Grenson or Church’s.

Cleaning is of the utmost importance with anything crisp and white. Consider purchasing a shoe-care kit from a specialist like Jason Markk to keep shoes looking their best.

Black Leather Chelsea Boots

Striking a balance between looking sharp and staying dry during the winter can be a sartorial conundrum. Let’s face it: Wellingtons and tailoring are never going to be a good look.

Instead, opt for a pair of black leather Chelsea boots to resolve your winter footwear woes. The added length at the ankle will keep the elements out, while the sleek, smooth finish will enable them to complement anything from dress pants to jeans.

Then there’s the rock ‘n’ roll appeal.We defy you to name another footwear silhouette that can be legitimately worn with a Tom Ford suit or black denim anda leather jacket. It’s 10/10 for versatility.

Suede Desert Boots

The relaxing of dress codes has had many benefits. Not counted among them is the fact that some men have started to take ‘casual footwear’ as a byword for sneakers, and sneakers alone.

In reality, there are many non-athletic shoe styles that can be paired with weekend attire. Perhaps the most favourable of them all is the humble desert boot.

This shoe-rack essential is timeless, comfortable and adaptable. Choose a subtle, neutral colour like brown or beige to ensure maximum wearability, and wear with cuffed chinos and an OCBD for an effortless smart casual look.

Understated Canvas Sneakers

When the sun has put on his hat, nothing hits that sartorial summer sweet spot quite like a pair of understated canvas sneakers. They’re wallet-friendly, extremely laid-back and one of those rare items that actually looks good when it’s a bit beaten up.

This makes canvas sneakers the perfect companions for navigating the warm weather in style. Whether to go high-top or low-top is a matter of personal preference. However, the latterworksbetter with shorts and won’t leave you with unfortunate tan lines.

White is the tried-and-tested summer favourite, but don’t rule out other colours. Brands like Converse and Novesta have some nice, vibrant options that can work wonderfully, so long as the rest of your outfit is suitably toned down.

Brown Derbies

Selecting office-appropriate footwear sounds simple enough, but it can often leave even the most stylish men scratching their expertly groomed heads. While there are a number of options, a simple pair of brown Derbies tends to be the most reliable.

Derby shoes have been the business elite’s footwear of choice for as long as there has been a business elite. They offer smart looks and timelessness, while their open-lacing system yields increased comfort for schlepping from desk to dinner several times a week.

When shopping for a pair, brace yourself to splurge a little. These shoes will likely be used daily, so it pays to buy from the best. Stick to Goodyear-welted styles from trusted Northamptonshire shoemakers for guaranteed longevity.

Suede Loafers

There aren’t many shoes that can be legitimately worn with tailoring or a pair of shorts, but the suede loafer is one of them. If you frequently find yourself confused by the concept of ‘cocktail attire’ then this is the shoe for you.

Suede loafers come into their own when a little flair is required. Think summer weddings or birthday drinks – times for when your Oxfords are too formal and your desert boots too casual.

As touched upon, another way to style this modern classic is to wear it with shorts. Try them with a white polo shirt tucked into navy chino shorts for a Wimbledon-friendly weekend look.

Brown Leather Work Boots

Snow, rain, mud, dirt – the terrain winter can conjure up, even in the city, makes the cooler months a hazardous time for your usual footwear.

That’s where work boots come in. Tough, rugged and built to last, a pair of sturdy leather boots is perfectly equipped to deal with anything the winter throws at them.

As if that wasn’t good enough, when styled right, they look great too. Think ‘workwear’, to really nail the look. We’re talking flannel shirt, raw denim, chore jacket and maybe even a beanie thrown in for good measure.

For some quality options, check out what Red Wing and Danner have to offer.

Performance Sneakers

Love it or hate it, regular exercise is simply a fact of life if you want to stay fit and healthy. Having the right gear to wear is important, but none of it more so than the sneakers.

A good pair of athletic sneakers will offer adequate support, flexibility and breathability in equal measures. Knitted options will ensure all of this and more. Not to mention that they’re aesthetically pleasing. In fact, pick a pair in a neutral shade and there’s no reason they can’t be worn off the treadmill, too.