Six pairs of shoes that every gentleman should have in their wardrobe

From Tod's Driving Shoes to John Lobb's Chelsea Boots, these are your footwear essentials

Good shoes are the bedrock of the modern male 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 heavens, then, that it’s so easy to get the foundations right. Though we live in changing times, the heroes of the male shoe rack remain reassuringly constant. And here they are, spread at your feet by the publication who really ought to know. Tread carefully, for you tread in the finest.

Six pairs of shoes that every gentleman should have in their wardrobe

John Lobb Half Brogue

If you’re going to wear dress 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 cobbler’s biggest gift to the menswear canon (which is saying something: 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, and pulls off the magic trick that only a very well made shoe can manage: it makes everything above it look about ten times sharper.

Six pairs of shoes that every gentleman should have in their wardrobe

Sperry Boat Shoe

While sailing one summer on the Long Island Sound, 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 birth place.

Six pairs of shoes that every gentleman should have in their wardrobe

Clark’s Desert Boot

‘It will never sell.’ That was the verdict on Nathan Clark’s prototype desert boot when the grandson of the brand’s founder pitched it to the board. He’d poached the idea from the soft suede casual shoes that the 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, it’s been adopted by every subculture under the sun – from the London teddyboy to the riviera playboy; the Cool Britannia of the nineties to the understated chic of the New York millennial. 

Today, the desert boot does its best work with lightweight tailoring for a relaxed twist on formal wear, or with rugged jeans and knitwear for a casual weekend look.

Six pairs of shoes that every gentleman should have in their wardrobe

A Chelsea Boot

Practical yet elegant, versatile yet utterly unique, the Chelsea boot is the deeply successful marriage of country and city. Based on a horseman’s rough-and-ready jodphur boot, the Chelsea first appeared in its modern incarnation at the end of the nineteenth century as an emerging class of gentleman began to desire sleeker and more convenient footwear for their St James’ jaunts. 

The Chelsea didn’t get modern its name, however, until the 1950s, when a generation of long-haired, free-living, boot-wearing young pups descended on the Kings Road area of the Royal Borough. There is still something deeply traditional yet raffish and faintly artsy about most modern versions of the boot, and it can be styled accordingly.

Six pairs of shoes that every gentleman should have in their wardrobe

Tod’s Driving Shoe

The boisterous lovechild of the Italy’s two great obsessions, 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, defenseless suede for better pedal feel) the shoe has nonetheless become a stalwart of the modern male wardrobe, thanks, no doubt, to its relaxed lines and foot-swaddling comfort. 

Pair yours with rolled up chinos and a splash of ankle, and don’t be afraid to plump for a slightly more colourful model than you might otherwise allow yourself.

Six pairs of shoes that every gentleman should have in their wardrobe

Gucci Horsebit Loafer

The Gucci loafer has lived a charmed life. From the Gatsby-esque origins of the house’s founding father – who annexed the infamous horsebit snaffle from the equestrian obsessions of his British aristocrat friends – to the riviera playboys of the 1960s and 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 a casual dress code (try them sockless in the summer for a dose of ageless sprezzatura) and will also drip a little decadence onto formalwear or black tie ensembles.

Further Reading