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The Most Iconic Men’s Boots Ever Made

Last updated: 02-07-2018

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The Most Iconic Men’s Boots Ever Made

Men have been wearing boots for at least 3,000 years, so we’re going to hold our hands up here. What follows does not include calfskin ankle boots designed by Inca warriors or mankind’s original winter boots, which were made by Inuit tribes and decorated with seal intestines. Sorry about that. What it does include, however, are classic 20th-century designs that do what the best boots have always done: they work.

Fashion rarely gets more functional than this. Whether you’re talking military stompers, steel-capped workers or rootin’-tootin’ cowboy boots, they’re all built for purpose. The fact that they look good is, in most cases, a happy coincidence.

These days, you might not work on the docks. Perhaps your feet only need protection from deceptively deep puddles. But if you want to look rugged and stylish at the same time, in footwear that will last longer than almost anything else in your wardrobe, this is what you should have on your feet.

Having shod the feet of Allied troops in two world wars, traditional Northamptonshire shoemaker Grenson is more than qualified to offer the smart, functional footwear when you need to look suited and booted. The firm, founded in 1866, was among the first to adopt the famous Goodyear welting technique, but its triple welt boot proves that it’s still innovating more than 150 years later.

Launched in 2014, the triple welt gives the brand’s classic brogue boot an even chunkier sole, adding width and height to a design that was already hard-wearing and nigh-on watertight. Designed to last you winter after winter, the sole will wear as slowly as the dapper brogue details date.

“Grenson provides practicality with its hiking-inspired eyelet lacing and sturdy Goodyear-welted soles, but also through offering a contemporary vibe with brogue detailing,” says Mr Porter style director Olie Arnold.

For meetings in the city, the pebble-grain leather pairs expertly with flecked wool trousers, but don’t mistake them for a strict Monday-to-Friday option. “These boots will always give a rakish look when teamed with denim jeans,” says Arnold.

A classic variation of polo-inspired chukka boots, the key difference is the casual and exceedingly comfortable crepe sole. Nathan Clark, whose grandfather founded the eponymous shoe store in 1825, first noticed the style on the feet of British troops in Myanmar in World War II. He sent sketches back home, and the design has remained virtually unchanged since 1950.

“As [footwear] staples go, this is quite possibly one of the most important pairs you’ll own,” says Sarah Ann Murray, a stylist who has dressed the likes of Samuel L. Jackson and Kit Harrington. “What’s particularly relevant about them, given the ankle height, the weight of the boot and its fabric, is that they complement all heights and builds and pretty much all trouser styles, even suit trousers.”

“Clarks offers a handsome colour palette with clean lines and unfussy finishings, though you can’t go wrong with chocolate brown if you can only pick one,” says Murray. “They’re perfect weekend attire, great paired with casual trousers or smarter jeans and offer a cool alternative to luxury sneakers.”

A bona fide cultural icon, this boot – famously worn by The Who’s Pete Townshend and a whole generation of skinheads – is about shit-kicking rebelliousness. It’s punk. It’s self-expression. So it’s funny that it was dreamt up by a German bloke with a dodgy foot. Dr. Klaus Maertens came up with the idea of an air-cushioned sole while recovering from a foot injury. At first, the innovation appealed mainly to elderly women and postmen, but then came the 1960s and 1970s, and with them, counterculture’s adoption of workwear styles.

Today the 1460 boot (named after the date production began – 1 April 1960) is available in dozens of finishes, numerous collaborations, lightweight soles or – if you really want to rebel – vegan leather. “It’s one boot we all ought to own, never throw away and let that classic yellow stitching and cherry finish patina to perfection,” says Murray. “Dr. Martens bridge the gap between rebel style and hardcore functionality. But it’s their unconventionality that forms part of the appeal. Decades of nonconformists usurping the latest sneaker trend, or overpriced bourgeois luxury boots, has elevated DMs to an almost cult-like status.”

“When you want to add just a nod of inner rebel and a confident edge to your ensemble, they’re perfect to rock with an upscale workwear look, or tapered pleated trousers and a casual jacket,” says Murray.

“Then for a full off-duty model look, of course, skinny jeans, a leather jacket, check flannel shirt or any one of the above will complete the punk roots of this boot – but you don’t have to be Joey Ramone to wear them with panache.”

Nancy Sinatra presumably approves of Timberland’s iconic style because this boot was made for walking. Thick treads and a cushioned ankle make for a comfortable hike while sealed seams keep the rain from leaking through that famous wheat-yellow nubuck. But, 40 years after they were first designed, the 6-Inch is, if anything, more comfortable on the tarmac than the open countryside.

“They are proof that function and fashion can, in fact, go hand in hand,” says celebrity stylist Alex Longmore. “They stood the test of time on the style front, are de rigueur in the wardrobes of seriously successful American rappers and are a favourite with the likes of David Beckham and his son Brooklyn.”

As well as appealing across the generations, this boot also strolls between fashion tribes. Outside of hip-hop, you’ll also find them in workwear outfits, while the range of colours they’re now available in mean they work with all kinds of tonal winter looks.

“The reason they are so popular is they are masculine,” says Longmore. “These legends look best worn with casual clobber.” So put your pleated trousers away and make like Kanye in some relaxed-fit jeans with a simple T-shirt and bomber jacket.

Chelsea boots were first designed by Queen Victoria’s bootmaker J. Sparkes-Hall in 1851 as an alternative form of riding boot, with an elasticated ankle that made them easy to slip on and off. The high society connection survives to this day, but such an elegant boot is tougher than it looks.

“R.M. Williams’s Chelsea boot was built for durability and comfort to withstand the demands of the Australian outback,” says Arnold. “The fact that these handcrafted boots are still worn and celebrated today highlights the level of expert craftsmanship,” Arnold says. “Investing in a pair of these will guarantee you lasting style and substance.”

Today the silhouette may be more synonymous with menswear bloggers than Mick Dundee, but its origins should be all the proof you need that the Goodyear-welted style is as resilient as it is dignified.

Despite the Chelsea boot’s outback credentials, resist the urge to team them with a ripped shirt and cork hat. One of the few boots you can wear with a suit, the design is nevertheless more comfortable a couple of dress codes down. Ideal for getting your date-night outfit off on the right foot, wear them with slim-fit jeans or tailored trousers, some fine-gauge knitwear and either an overcoat or leather jacket, depending on the season.

These days you’ll more likely see Red Wings on the feet of creatives and baristas, but the brand’s moc toe design was first made for farmers and factory workers in the mid-20th century. It comprises reassuringly sturdy uppers on a lightweight crepe sole with minimal tread underfoot to reduce the mud that would cling to the boots at the end of the working day.

They’re grafters, too. Goodyear-welt construction and triple stitching will ensure these boots put in a long shift and if you look after the oil-tanned leather, it will age better than you will. “Work boots from Red Wing are legendary [for their] quality, unsurprising since the brand has been making boots in the US since the turn of the 19th century,” says Arnold. “They are practical, rugged and offer a vintage workwear look that can be worn for years to come.”

What was originally made to wear with overalls, today looks best with another workwear staple: denim. The round moc toe and contrast white sole suits a look that mixes pinrolled indigo jeans, a flannel shirt and a worker jacket. If you have to clock on, you might as well look good.

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