Good shoes are the lifeblood of a man’s wardrobe – the foundation on which everything else rests. Do you remember what happened to the man who built his house on sand? Well, neither have we, but we’re pretty sure it has something to do with him torpedoing a job interview by marrying a leaky pair of sneakers with an otherwise perfectly good suit. Thank goodness, then, that it is so easy to lay the right foundation (with a little know-how). Even though we live in changing times (celebrity presidents, mustaches, return of the fanny pack), the heroes of the shoe rack remain reassuringly consistent. To help you do your best all year round, we’re bringing you 10 of the most iconic shoes and boots of all time.

Timberland Classic 6-Inch Boot

The Timberland boot never wanted to be an icon. A humble and deeply practical work shoe designed for New England laborers, the Original Yellow Boot was designed to outlast all of its competition and, most importantly, keep its owners’ feet warm and dry for long. the snowy winters of the east coast. It did so through a combination of thick nubuck leather, 39 separate pieces, a revolutionary welt sole, and a lengthy 80-step construction process. But then the ’90s arrived, and a hip-hop movement obsessed with larger-than-life clothing and high-top shoes dragged the Timberland boot from the construction site down the street. And then the word got out. Still made from the sturdy and practical materials of its 1973 prototype, the Prerequisite Work Boot is a design legend doing its best today with selvedge jeans and chunky knits.

Authentic Sperry Original Boat Shoe

While cruising one summer on the Long Island Sound estuary just off New York City, shoemaker Paul A Sperry slipped on the deck of his topper and fell overboard. After hoisting himself onto the deck, the inventor decided to develop a sports shoe that even held up on the wet surface of a sailboat. That’s what he did with the Sperry Top-Sider: a rubber-soled deck shoe engraved with a revolutionary herringbone texture that maximizes traction without adding bulk. Lightweight, durable, and featuring a flattering low upper, Sperry boat shoes look just as good today with dark chinos and chic, relaxed basics as they do among the preppy slouch of his birthplace on the East Coast.

Clarks Originals Desert Boot

“It will never sell.” This is the verdict of the prototype desert boot designed by Nathan Clark (grandson of the founder of the British brand) when he presented it to the board. Clark came up with the idea for the casual model’s shoe in soft suede that British officers wore while stationed in Burma – crepe-soled high-top boots that were lightweight, durable and flexible enough to adapt to varied terrain. of the desert. Undeterred by old guard reservations, Clark unveiled his creation at the Chicago Show Fair in 1949, where his sleek figure and chunky sole captured the imagination of the world’s fashion press. In the decades since, the desert boot has been embraced by almost every subculture in the sun – from London mods to the Playboy Riviera; 90s Cool Britannia with understated New York millennial chic. Still one of the best boots in men’s clothing, today it’s more comfortable with a light fit for a casual touch on evening wear, or with raw jeans and knits for a weekend look. relaxed end.

Converse Chuck Taylor All Star

The Chuck Taylor All Star recently celebrated 100 years of sale, but the deceptively simple canvas and rubber sneaker is fresher than ever. It is therefore no wonder that it remains one of the most successful types of shoes in history, with the American firm moving more than 200,000 pairs a day. Although initially designed as a technical basketball shoe (the soft canvas high top shoe was designed to move more naturally with a long athletic sock and thus cause fewer blisters), basketball has become one. the most versatile shoes in history. With its clean lines and forgiving materials, the All Star feels right at home in almost any setting, while its countless colourways and endless reincarnations ensure the style stays relevant where other shoes falter.

Sandal Birkenstock Arizona

You know you’ve created an icon when its name is hijacked and turned into a political insult. During the 2004 presidential race, hippie supporters of favorite Howard Dean were lightly referred to as “Birkenstock Liberals” to the delight of the mainstream press. Well, we can think of worse brushes to be tared with. After all, the Birkenstock sandal is a very impressive piece of engineering and pretty much the only shoe in the much-maligned sandal category that has stood the test of time. Although its revolutionary arch support was developed almost a century ago, the shoe remains the benchmark for ergonomic and foot-friendly design. The sturdy combination of cork and leather, meanwhile, gives the sandal a timeless style and heavy environmental credentials. We’d go for the classic chocolate colourway in its relaxed two-strap embodiment – pair it with natural tones and blue denim in spring, or chino shorts and linen shirts when summer sets in.

Dr Martens Chelsea Boots 2976

Dr Martens’ most famous shoe is the eight-eyelet boot – a chunky sole that turned the brand of an obscure workwear manufacturer (the boot was first marketed as a gardening aid) into a symbol of counter-culture and rebellion. But for our money, the British brand’s biggest contribution to the modern wardrobe is its on-trend take on the Chelsea boot. With its classic gum rubber sole, this Goodyear-stitched shoe has dragged the traditional Chelsea boot from riding school to the streets of London to the ’60s center of King’s Road and the rock’ n ‘roll styles of the Rolling. Stones. Today, it plies its trade like a raw version of its more formal cousin, with a floating air-cushioned heel and all-season tread. Worn with rolled up jeans or dark chinos, it’s a practical way to winterize a chic, casual outfit.

Tod’s Gommino driving shoe

The noisy son of love of Italy’s two great obsessions (driving and style), the driving shoe is a European icon crying out for the heat and drama of the race track. Deeply impractical on paper – the best driving shoes have a soft, defenseless suede exposed belly for better pedal feel – the shoe has nonetheless become a mainstay of the shoe rack, thanks, no doubt, to its lines relaxed and comfortable to swaddle the feet. You don’t have to be Neapolitan to pull them off, mind you. Pair it with rolled-up chinos and a touch of ankle cuffs, and don’t be afraid to go for a slightly more colorful style than you might otherwise afford.

Gucci Horsebit loafer

the Gucci moccasin lived an enchanted life. From the Gatsby-esque origins of the house founder (who nipped the bit out of the equestrian obsessions of his aristocratic friends) to the blue-blooded Sloane Rangers of the 1980s (not to mention a thousand Wall Street brokers, international diplomats and from Ivy Trust-funders of the League along the way), the shoe has long been the common denominator of the upper crust. Strangely durable and sturdy despite their famous flexible and lightweight construction, GucciHorse bit moccasins are a serious investment piece and perhaps the one shoe that you wouldn’t be silly to include in your will. They also look great underneath almost anything: the right pair adds a touch of glitz and continental chic to a casual outfit (try them sockless in summer for a dose of ageless sprezzatura), and will also drip from a little decadence on an evening dress or a black-tie penguin. suit.

Joint projects Achille bas

Not all icons are durable. The Common Projects sneaker is just over a decade old, but the cult tennis shoe has already drawn an audience equal to its older counterparts. With a sleek profile that lends an upscale feel to the classic low-top form, Common Projects has set the new standard for high-end athletic shoes and minimalist sneakers. The iconic all-white upper stands out 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 worthy of the name, the sneaker is more than happy to break the rules: wear it with anything from distressed denim and casual chinos to formal jumpsuits and both. pleated pieces.

John Lobb Demi Brogue

If you are going to buy a pair of stylish shoes, you will want to choose half brogues. And if you’re wearing half brogues, you’ll want to go for the original and the best. An elegant compromise between the more ornate wing-tip Oxford and the professional-looking Oxford, John Lobb first presented his demi-brichelieu at the Paris exhibition of 1937. It could well be the largest shoemaker’s gift to menswear (which means something, seen as Lobb also perfected penny loafers and pioneered the shape of the modern Chelsea boot). Imitated everywhere but never improved, John Lobb’s quintessential dress shoe lends a reassuring touch of quality to any formal ensemble. Plus, it pulls off the magic trick that only a very well-made shoe can do: it makes anything worn over it look about 10 times sharper.