Good shoes are the bedrock of a man’s wardrobe – the foundation on which everything else lies. Do you remember what happened to the man who built his house on sand? Well, neither do we, but we’re pretty sure it had something to do with him torpedoing a job interview by marrying a pair of leaky plimsolls with an otherwise perfectly good suit.

Thank the heavens, then, that it’s so easy to get the foundations right (with a little know-how). Though we live in changing times (celebrity presidents, moustaches, the return of the bum bag), the heroes of the shoe rack remain reassuringly constant.

To help you put your best foot forward all year round, we present 10 of the most iconic, unique shoes and boots of all time.

Timberland Classic 6-Inch Boot

The Timberland boot never wanted to be an icon. A humble, deeply practical work shoe designed for the laborers of New England, the Original Yellow Boot was built to outlast all its competitors and, crucially, keep its owners’ feet warm and dry during the snow-addled East Coast winters.

It did that through a combination of thick-cut nubuck leather, 39 separate parts, a revolutionary welted sole and a lengthy 80-step construction process. But then the nineties came along, and a hip-hop movement obsessed with larger-than-life garments and high-cut statement shoes dragged the Timberland boot from the worksite to the streets. And then the word was out.

Still made from the sturdy, no-nonsense materials of its 1973 prototype, the prerequisite work boot is a design legend that today does its best laboring teamed with selvedge jeans and chunky knits.

The Best Timberland Boots


Sperry Authentic Original Boat Shoe

While sailing one summer on the Long Island Sound estuary just off New York, shoemaker Paul A Sperry slipped on the deck of his topper and fell overboard.

After hauling himself back on deck, the inventor resolved to develop a sports shoe that held its grip even on the damp surface of a sailing boat. This he did with the Sperry Top-Sider: a rubber soled deck shoe engraved with a revolutionary herringbone texture that maximized traction without adding bulk.

Lightweight, hard wearing and with a flattering low-cut upper, the Sperry boat shoe looks as good today with dark chinos and smart-casual staples as it does amongst the preppy slouch of its East Coast birthplace.

The Best Sperry Boat Shoes


Clarks Originals Desert Boot

“It will never sell.” That was the verdict on the prototype desert boot designed by Nathan Clark (grandson of the British brand’s founder) when he pitched it to the board. Clark poached the idea for the shoe from the soft suede casual model that British officers wore while stationed in Burma – crepe soled, high-topped boots that were light, durable and flexible enough to handle the varied terrain of the desert.

Undeterred by the reservations of the old guard, Clark unveiled his creation at the Chicago Show Fair in 1949, where its sleek silhouette and chunky sole captured the imagination of the world’s fashion press. In the decades since, the desert boot has been adopted by almost every subculture under the sun – from the London mods to the Riviera Playboy; the Cool Britannia of the nineties to the understated chic of the New York millennial.

Still one of menswear’s best boots, today it’s most at home with lightweight tailoring for a relaxed twist on formalwear, or with raw denim jeans and knitwear for a casual weekend look.

The Best Clarks Desert Boots


Converse Chuck Taylor All Star

The Chuck Taylor All Star recently turned 100 year sold, but the deceptively simple canvas and rubber sneaker feels as fresh as ever. It’s little wonder, then, that it remains one of the most successful types of shoe in history, with the US firm shifting more than 200,000 pairs a day.

Though initially conceived as a technical basketball shoe (the soft canvas high-top was designed to move more naturally with a long gym sock, and thus cause fewer blisters) the unique shoe has become one of the most versatile pieces of footwear in history.

With its clean lines and forgiving materials, the All Star feels at home in almost any setting, while its countless colorways and endless reincarnations ensure the model stays relevant where other shoes waver.

The Best Converse All-Stars


Birkenstock Arizona Sandal

You know you’ve created an icon when its name is hijacked and repurposed as a political slur. During the 2004 Presidential race, frontrunner Howard Dean’s hippie-ish supporters were referred to slightingly as the ‘Birkenstock Liberals’, much to the delight of the mainstream press.

Well, we can think of worse brushes to be tarred with. After all, the Birkenstock sandal is a seriously impressive piece of engineering and just about the only shoe in the much-maligned sandal category that has stood the test of time. Though its revolutionary arch support was developed almost a century ago, the shoe remains the gold standard in ergonomic and foot-friendly design. The rugged combination of cork and leather, meanwhile, lends the sandal both timeless styling and heavyweight environmental credentials.

We’d opt for the classic chocolate colorway in its laid-back two-strap incarnation – match it with natural tones and blue denim in the springtime, or chino shorts and linen shirts as summer settles in.

The Best Birkenstock Sandals For Men


Dr Martens 2976 Chelsea Boot

Dr Martens’ most famous piece of footwear is the eight-eye boot – a chunky-tread stomper that transformed the brand from a maker of obscure workwear (the boot was first marketed as a gardening aid) to a symbol of counterculture and rebellion. But for our money, the British brand’s most significant contribution to the modern wardrobe is its moddish take on the Chelsea boot.

With its classic gum rubber sole, this Goodyear-welted shoe dragged the traditional Chelsea boot from the riding school to the streets of London via the swinging sixties’ hub of the King’s Road and the rock ‘n’ roll stylings of the Rolling Stones.

Today it plies its trade as a rough-and-ready take on its more formal cousin, with a buoyant air-cushioned heel and all-weather tread. Worn with pin-rolled jeans or dark chinos, it’s a no-nonsense way to winterproof a smart-casual outfit.

Best Dr Martens Chelsea Boots


Tod’s Gommino Driving Shoe

The boisterous lovechild of Italy’s two great obsessions (driving and style), the driving shoe is a European icon that screams for the heat and drama of the racetrack.

Deeply impractical on paper — the best driving shoes have an exposed underbelly of soft, defenceless suede for better pedal feel — the shoe has nonetheless become a stalwart of the shoe rack, thanks, no doubt, to its relaxed lines and foot-swaddling comfort.

You needn’t be Neapolitan to pull them off, mind. Pair yours with rolled up chinos and a splash of ankle, and don’t be afraid to plump for a slightly more colorful model than you might otherwise allow yourself.

Best Tod's Driving Shoes


Gucci Horsebit Loafer

The Gucci loafer has lived a charmed life. From the Gatsby-esque origins of the house’s founder (who pinched the horsebit snaffle from the equestrian obsessions of his aristocratic friends) to the blue-blooded Sloane Rangers of the 1980s (not to mention a thousand Wall Street power brokers, international diplomats and Ivy League trust-funders along the way), the shoe has long been the common denominator of the upper crust.

Eerily long-lasting and hardy despite their famously supple and lightweight construction, Gucci’s horsebit loafers are a serious investment piece and perhaps the only shoe that it wouldn’t be silly to include in your last will and testament.

They also look good below almost anything: the right pair adds a knowing flashness and a continental chic to casual dress (try them sockless in the summer for a dose of ageless sprezzatura), and will also drip a little decadence onto formalwear or black tie penguin suits.

The Best Gucci Horsebit Loafers


Common Projects Achilles Low

Not all icons are long-lived. The Common Projects sneaker is little over a decade old, but already the cult tennis shoe has garnered a following to match its older counterparts.

With a sleek profile that lends an upmarket feel to the classic low-top shape, Common Projects has become the new standard in high-end sports shoes and minimalist sneakers. The iconic all-white upper is set apart from the crowd with an understated gold serial number, while the supple Saffiano leather ensures the product matures and improves with age.

And, like most icons worth their salt, the sneaker is more than happy to break the rules: pair with anything from distressed denim and relaxed chinos to formal suit separates and pleated two-pieces.

The Best Common Projects Sneakers


John Lobb Half Brogue

If you’re going to buy a pair of smart shoes, you’ll want to choose half-brogues. And if you’re going to wear half brogues, you’ll want to select the original and the best.

An elegant middle-ground between the more ornate wingtip brogue and the business-like Oxford, John Lobb first presented his half brogue at the Paris Exhibition of 1937. It may well still be the cordwainer’s biggest gift to menswear (which is saying something, seeing as Lobb also perfected the penny loafer and pioneered the shape of the modern Chelsea boot).

Imitated everywhere but never bettered, John Lobb’s quintessential town shoe lends a touch of reassuring quality to any formal ensemble. Plus, it pulls off the magic trick that only a very well made shoe can: it makes everything worn above it look about 10 times sharper.

The Best John Lobb Half Brogues


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