Stylish and functional, there’s a reason Americana-inspired workwear is a mainstay of a man’s wardrobe.

Look up a definition of fashion and you will probably find something along the lines of “the latest style of clothing”, so it might seem counterintuitive that one of the biggest trends in menswear continues to be a style of clothing that dates back a century or more – workwear.

It is this very longevity that is a large part of workwear’s appeal as it evokes a time when ranchers and prospectors were opening up the West and needed clothes that were built to last – such as Mr Levi Strauss’ eponymous riveted denim trousers that had already become a favourite of miners and cattlemen in the 1870s. And great quality and durability means good value.

Not only does workwear last well, it wears well, adapting itself over time to the wearer’s body and, as form follows function, developing a unique patina. With any luck, having been around for 100 years or so already, it’s unlikely suddenly to go out of style.

The key to pulling it off is to keep things simple: use block shades of dark blue or neutral colours such as sand, stone and khaki and keep the silhouette clean. Don’t be afraid to mix and match individual pieces. And make sure the fit is relaxed – jackets should be roomy enough to layer pieces underneath. If you want a pop of colour or pattern you should look out for a lumberjack shirt.

The classic overshirt is a wonderfully practical piece, allowing men to enjoy an extra layer of protection without being weighed down. It also happens to be an ideal between-season piece. Try pairing an overshirt in a complementary but lighter colour over a button-down shirt (to keep your neckline clean). The classic combo is navy and chambray, but any pale blue or white will work just as well. Or wear it open with a white T-shirt. The generous patch pockets are perfect for phones, wallets, earphones and beanies.

For a more hipster vibe, see the section on plaid. In colder weather, wear over a chunky rollneck or under a peacoat.

Every man should have a loose-cut field jacket in his wardrobe. When it comes to workwear, these work best in a neutral colour such as off-white, pale mustard or khaki to contrast with the indigo denim dye. As these jackets are cut short, they should be buttoned high to the neck, leaving the lower half unfastened. While the jacket will twin well with nothing more than a white crew-neck T-shirt, when the weather is less clement it can be layered over a high-tech padded jacket or lightweight gilet for a layer of insulation.

Look after them and a rugged pair of boots will last for years. You can go for a leather sole or, like these Red Wings Classic Moc (above), a Goodyear-welted gripped rubber sole. Pair with loose-cut utility-style trousers, such as cargo pants, but rolled up to the ankle to show more boot. Because if you have the best boots, why not flaunt them? As spring arrives,  this look works well with a pair of Converse Chuck Taylors and lightweight chinos.

The only trousers that come close to rivalling jeans in this trend are classic chinos in camel or stone. The double-pleated front here is both stylish and comfortable. These come up fairly high, so wear them with a slouchy top that sits on the waist and on the pleats. They work particularly well worn slightly shorter in the leg, sitting on your shoes without breaking.

Workwear should never be worn tight to the body. Not only does this allow movement, it also means jackets can be worn on top of layers, according to the weather. The rule is to keep it simple. Just as you wouldn’t expect an old-school cowboy to be wearing a Metallica T-shirt on the ranch, so you should keep everything understated and logo-free. Start with the longest layer first – the shirt – and build up, making sure each layer is visible.

There is more to workwear than denim and cotton drill. For outerwear, try pieces in wool and tweed, and for extra protection, rather like cotton, wool can be waxed. The look is redolent of the great outdoors, so look for details such as chunky buttons and generous pockets. Twin with wide-legged jeans or, for a smarter take on this weekend look, with a rollneck, tailored chinos and suede loafers.

The chore jacket is a classic workwear piece, especially in waxed cotton or wool. It was once the uniform of the jobbing photojournalist, thanks to its roomy pockets that were perfect for rolls of film. In wool, the look also works well smartened up as a laid-back blazer with a knitted tie and brown brogues. In cotton it is more casually paired with cargo or carpenter pants.

The American love affair with plaid dates back to the mid-19th century, inspired by the tartans of the Scottish clans – the word “plaid” is derived from the Gaelic word for blanket. It soon became a staple for workers – most notably lumberjacks, thanks to a 1914 ad campaign for the Red River Lumber Company that featured the mythical giant lumberjack Paul Bunyan in plaid shirts. It is great for adding a splash of contrasting colour and works particularly when used on a soft fannel padded overjacket layered over denim shirts. Or just go for a straight plaid shirt over a white tee under a chore jacket.

The men featured in this story are not associated with and do not endorse MR PORTER or the products shown