In almost every instance, it’s advisable to steer clear of indigenous clothing. So much damage has been done by folks wearing headdresses to festivals or sports societies in hachimaki headbands that our default position on wearing garms with a cultural resonance to which you are not privy is simply: “nah, pal.”

But there are exceptions. Some clothes transcend their roots to become not just okay, but essential. Take the parka, a winter coat ripped off from an Inuit original by the US military in the 1950s. Wear one today, and you’d be tarred as an Oasis fan, rather than a racist. (Your call on which is worse.) It’s the same deal for moccasins, which have been traditional Native American footwear for thousands of years but have crossed over into high fashion too, inspiring everything from loafers to work boots and even trainers.

“They are a classic,” says Luke McDonald, a stylist at personalised online menswear store Thread. “They can be styled to dress down a preppy look, but they also have a great hippie heritage and look ace with double denim or more relaxed ensembles.”

Red Wing HeritageRed Wing Heritage

The OG versions were designed to protect the foot while still letting the wearer feel the floor, and are still incredibly comfortable. “If you’re going for a classic moccasin style, try and find native makers who are producing them. They usually aren’t too pricey and are often made from unique North American hides like caribou, elk or bison.”

Of course, while going traditional has its authenticity merits, it does also put you in, to put it delicately, the mung beans and healing crystals camp. Like people who wore Birkenstocks before designers got their hands on them.

Lucky you, then, that labels have seen fit to take some of the moccasin’s most appealing features – that pie-crust toe lip in particular, but also more decorative details like ankle fringing and leather laces – to give contemporary shoes a timeless feel.

ClarksClarks

These stylistic shifts will also ensure no accusations of insensitivity, says McDonald. “You’re looking at quite a different shoe, and it won’t be mistaken for cultural dress-up. Moccasins are by their nature a casual, earthy style, so you want an outfit that has a rugged feel. Nothing too formal. A dress shirt and chinos for something vaguely Riviera is as smart as it gets.”

And, it pays repeating, no headdresses, war shirts or Washington Redskin football jerseys. Ever.

Four Contemporary Spins On The Moccasin

The Moccasin Sneaker

Clarks leads the way on the mash-up between street- and prairie-wear. The British brand’s Trigenic Flex model is particularly innovative for its blend of classic uppers and futuristic sole, but trainer behemoths Nike and Adidas have also dabbled in mocs.

The former’s Solarsoft took its style cues from the Apaches’ moccasin and its signature upturned toe. Meanwhile, the German firm has slapped everything from toe stitching to leather fringing on a glut of silhouettes.

“They echo traditional moccasin styles but for a more modern, trainer-obsessed world,” says McDonald. Keep the styling up-to-date, either with denim or slim joggers. “They’re great for making a statement without a mad logo or loads of colour. It’s something distinctive, modern but minimal.”

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Moc Boots

In 1950, Red Wing released the Red Setter boot, the first of its kind to feature that signature moccasin stitching on the toe box. When the design detail migrated to its 875 work boot a few years later, a template was set.

“The moccasin toe is derived from the hunting moccasin styles of the late 19th century,” says McDonald, “but made in a heavy-duty leather, for foresters and factory workers.”

Moc boots are a key part of any serious workwear wardrobe, although admittedly now are more often seen in creative studios than anywhere near an assembly line. “They look great with any heritage style – think tough denim, canvas jackets and flannel shirts.”

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Classic Moccasin

Leaning authentic with your moccasins sounds troublingly WOMAD, but it can work. Mid-top boots, usually in a tactile suede with crepe soles, have some serious menswear heritage, adopted by several different style tribes.

Clarks Wallabees (a moc-inspired version of desert boots) are a cultural staple in Jamaica and closely associated with reggae style, but they’re also big with hip-hop and Britpop crowds (Richard Ashcroft wore them in the video for Bittersweet Symphony). “This is a defiantly casual style, so you want to pair it with some well worn wide leg chinos or beat up jeans.”

The Best Moccasins For Men

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Driving Shoes

What do you get if you mix Native American ingenuity with Italian flair? “Somewhere between a traditional native moccasin and a penny loafer, this louche Italian take is the smartest variety,” says McDonald.

From above, driving shoes look like a streamlined spin on old-school mocs, with a cleaner toe stitch and penny loafer-alike saddle strap. But flip them over, and you’ll see a sole covered in rubber grommets, to help your feet grip the pedals of your classic sports car.

Their styling cues are less guy-who-wears-a-Ferrari-hat-on-the-bus, more Gianni Agnelli on vacation. “They look great with a loose cut suit or a pair of drawstring or pleated trousers. The vibe you’re after is elegant but relaxed.”

The Best Driving Shoes For Men

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