Best Foot Forward: The Most Iconic Men’s Shoes Ever Made

Do you know how many new footwear styles hit retailers’ shelves every year? Neither do we, there aren’t any statistics available on that. But we do know it’s a lot; far too many to count. And while 99% of them are destined for the sales come next season, a select few will live on through the ages, shaping the footwear landscape for decades, perhaps even centuries to come.

Those are the styles worth investing in. The classics; the icons; the styles that industry nerds like us will still be penning articles about 100 years from now. Why? Because they’re unique, timeless and have carved their own path. In short, they’re the best shoes ever made; the shoes every man should own… or at least know about.

That’s why we decided to curate a definitive list of these influential footwear styles, complete with a bit of history and some quickfire styling tips on each. Here you’ll find everything from loafers to high tops, all united by their shared iconic status.

Clarks Desert Boot

The Clarks Desert Boot might just be our all-time favourite smart-casual shoe. It’s been a menswear mainstay since its launch in the 1950s and imitated ad infinitum, but to the best of our knowledge, never bettered.

The style itself was inspired by founder Nathan Clark’s deployment in Burma. He spotted Burmese soldiers wearing simple crepe-soled boots and decided to bring the concept to Western shores. Clark’s version features a double-eyelet lacing system, a mid-height shape and that same crepe-rubber sole that caught his eye all those decades ago.

Buy now at MR PORTER

Wear It With

Anything ranging from casual to smart-casual. The best thing about the desert boot is its versatility.

Dr. Martens 1460 Boot

Over the decades, this classic piece of footwear design from Dr. Martens has proved that even the scariest of subcultures can have a soft side. Albeit the object of their warmness and affection does happen to be a massive leather boot.

From punks to skinheads to heavy metallers, the 1460 has been a staple for them all, earning its place in the Footwear Hall of Fame and cementing its reputation as a countercultural icon. However, it’s not all skulls, daggers and tattooed knuckles – the 1460 is actually surprisingly versatile and well deserving of a spot in any style-savvy man’s footwear rotation.

Buy now at Dr Martens

Wear It With

Grungy staples like flannel shirts, black jeans and slouchy knitwear.

Timberland 6″ Boot

Also known as the Original Yellow Boot, this waterproof workhorse evolved above and beyond its functional roots and became a fully-fledged cultural phenomenon. It was originally designed for the white working class of New England but later became a piece of Black history when it was adopted by East Coast rap pioneers in the 1980s and 1990s.

Today the 6” boot remains largely unaltered, and for good reason. After all, this is one of the most recognisable and often-imitated boots ever designed. A must for anyone who likes their footwear big and bold.

Buy now at END.

Wear It With

We think this boot works best with workwear staples. Think chore coats, raw denim and heavy casual shirts.

Gucci Horsebit loafer

Since its launch in the early 1950s, the Gucci horsebit loafer has been a beacon of opulence and elegance, unconstrained by demographics or dress codes. It’s the sort of shoe that can add a little sparkle of luxury to any outfit, whether it be a tuxedo or a T-shirt and shorts.

Now in its eighth decade, this simple slip-on has shown the world the power of the loafer as an all-bases-covered shoe and remains something that every style-conscious man should aspire to own at some point in his life.

Buy now at MR PORTER

Wear It With

A surprising amount of outfits ranging from ultra dressy to the super laid-back, that’s the beauty of it.

Church’s Shannon Derby Shoe

The Derby shoe is such a ubiquitous style that it’s almost impossible to single out any one version as the benchmark. Still, if you put a gun to our head, we’d probably say the Shannon Derby from English shoemaker Church’s is the Derby against which all others should be measured.

The Shannon Derby shoe has been popular since its launch in 1970 and while some footwear aficionados talk about a drop in quality since the brand was purchased by Prada, we’ve seen no evidence of this. In fact, the shoes are still handmade in Northamptonshire and boast the same clean good looks that first made them a hit all those years ago.

Buy now at FarFetch

Wear It With

A well-cut suit.

Sperry Authentic Original Boat Shoe

When Paul Sperry set to work replicating his dog’s ability to hold fast on slippery surfaces, little did he know he was about to create one of the most iconic summer shoes of all time. With its unique tread pattern, the Sperry Authentic Original boat shoe allowed affluent North-Eastern sailors to keep their traction on wet decks and became a symbol of preppy East Coast style in the process.

Aside from a grippy sole, the shoe features a moc-toe construction, leather laces and additional leather-lace detail to the sides.

Buy now at END.

Wear It With

Preppy, smart-casual pieces like Oxford shirts, chinos, cardigans and soft tailoring.

Converse Chuck Taylor All Star

Shoes don’t come much more iconic than Converse’s classic Chuck Taylor All Star. It’s impossible to overstate the significance of this simple canvas sneaker within the context of modern footwear, but suffice to say it’s an important piece of design history.

We’re talking about the most popular sneaker in the world here. According to statistics from Footasylum, more than 60% of Americans own a pair. The secret to the shoe’s success? Its simplicity. The All Star isn’t packed full of cutting-edge tech or weird and wonderful materials, it simply does what it does and does it well.

Buy now at SSENSE

Wear It With

Pretty much anything short of formalwear.

Adidas Stan Smith

It’s easy to forget that Stan Smith was an actual professional tennis player and not just a name on the tongue of a sneaker. That’s how famous his pro-model court shoe has become.

The Adidas Stan Smith might just be the ultimate minimalist sneaker. Clean and simple but so effective. It’s both one of the most instantly recognisable shoes out there and one of the most nondescript. It’s also far more accessible than some of the more coveted minimalist sneakers out there. And let’s face it, if not for the Stan Smith, those other shoes probably wouldn’t even exist.

Buy now at ASOS

Wear It With

Anything, but simple staples like plain tees, slim-fit denim and light outerwear work particularly well.

Nike Air Jordan 1

Sneaker culture is huge and it could be argued that the Air Jordan 1 is the shoe that started it all. It was NBA superstar Michael Jordan’s first pro model and remains the stuff of sneakerhead legend.

The Air Jordan 1 paved the way for one of the most hyped lines in footwear history. Some of the most sought-after kicks of all time have come courtesy of the Air Jordan brand and this classic basketball shoe is at the root of it all.

Buy now at Nike

Wear It With

Streetwear staples like hoodies, sweatshirts, bomber jackets, loose-fitting legwear and relaxed tees.

Red Wing 875 Moc Toe

From mechanics’ workshops in the Midwest to hipster coffee joints in south east London, the footwear of choice is the same. The 875 Moc Toe from Red Wing is a classic work boot with crossover appeal and has become synonymous with quality, durability and heritage Americana cool.

The great thing about a pair of Red Wings is that instead of deteriorating, they mature like a fine wine. They’re boots for those who adhere to the raw denim school of thought: the more you wear it, the more individual and characterful it ultimately becomes.

Buy now at END.

Wear It With

Heavyweight workwear classics like thick flannel shirts, raw denim, gilets and heavy outerwear.

Birkenstock Arizona

There aren’t many style preferences that unite bird-watching uncles and menswear influencers, but a penchant for chunky German sandals is most certainly one of them. The Birkenstock Arizona exists in a sort of quantum state: it’s both the coolest piece of footwear on earth and the most catastrophically uncool at the same time. Maybe that’s the secret to its success.

The re-emergence of wearing socks with sandals as a completely reasonable thing to do has seen the Arizona thrust into the spotlight once again. Only it never really went away in the first place. This super-comfy sandal is a resortwear essential and will always be stylish in the right setting. If you don’t already own a pair, there’s never been a better time to buy.

Buy now at East Dane

Wear It With

Camp-collar shirts, tailored shorts and sunglasses in the summer. Hoodies, joggers and your jazziest socks for WFH in winter.

Tod’s Gommino Driving Shoe

Italy: land of Lamborghinis, leather and, as a result, possibly the finest driving shoes known to man. The Tod’s Gommino is a loafer with a difference. Famous for its soft, suede underbelly and pebble sole, it’s designed to provide maximum feedback from pedals to driver and look the part while doing so.

Alongside the Gucci horsebit loafer, the Gommino is probably one of the most famous slip-on styles in existence. We love it for its character and the cheeky way it coaxes us into experimenting with footwear colours we might ordinarily write off.

Buy now at FarFetch

Wear It With

A dash of Riviera style. Think white legwear, a linen shirt and maybe even a little bit of ankle if you’re feeling particularly Mediterranean.

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.