10 Iconic Men’s Shoes & Boots

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, Leicester in the Champions League, Ed Balls thrusting in a sequined romper suit), the heroes of the shoe rack remain reassuringly constant.

To help you put your best foot forward in 2017, we present 10 of the most iconic shoes and boots of all time.

Timberland Boot


The Timberland boot never wanted to be an icon. A humble, deeply practical work shoe designed for the labourers 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 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 labouring teamed with selvedge jeans and chunky knits.



John Lobb Half Brogue


If you’re going to buy a new pair of smart shoes, you’ll want to choose half-brogues. And if you’re going to wear half brogues, you’ll want to choose 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 above it look about 10 times sharper.

Available at John Lobb.


Sperry 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 maximised 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 birth place.



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 in the desert – 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.

Today, the desert boot is most at home with lightweight tailoring for a relaxed twist on formalwear, or with rugged jeans and knitwear for a casual weekend look.



Converse Chuck Taylor All Star


The Chuck Taylor All Star turns 100 next year, but the deceptively simple canvas and rubber sneaker feels as fresh as ever. Though originally 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 less blisters) the trainer 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 colourways and endless reincarnations ensure the model stays relevant where other shoes waver.