No discussion of the history of 20th-century menswear would be complete without a mention of that classic piece of workwear turned casualwear, the denim jacket. The Levi Strauss Type I, from which most modern incarnations are generally considered to have evolved, can be dated back to around 1905, and yet the denim jacket still manages to remain wholly contemporary, weathering the passage of time and the ebb and flow of seasonal trends to earn itself a rightful place in the annals of men’s style.

This is an everyman garment in the truest sense of the word. While the hardwearing fabric and welt-reinforced seams serve as a reminder that it was originally intended for miners and railroad workers in the North American Old West, over the years, it’s been associated with just about every subculture going and today is worn by everyone from presidents to fashion designers. It’s not just the archetypal Levi’s-style trucker jacket that you can buy now, either. There are denim jackets in a broad range of styles from designers across the spectrum, including TOM FORD, Acne Studios, AMIRI and KAPITAL. But which should you choose and how should you wear it? The following images, captured by street-style photographers across the globe, should offer some inspiration.

This is an example of double denim done right. The subtly different washes of the jacket and the jeans, plus the addition of plenty of other layers – there’s a navy T-shirt, a white shirt and a quilted gilet before you get to the denim jacket – ensures this outfit avoids Canadian tuxedo territory. (Tip: if you’re wearing two articles of the same fabric, a bold contrasting layer helps to break them up. In the case of dark-blue denim, the obvious choice is a white T-shirt.) Also of note here is how our subject has opted for a longer, more generous cut of jacket better to accommodate all of those layers. If he’d tried this with a standard cropped trucker jacket, he would have ended up looking like the Michelin man.

Denim, like leather, is a fabric that gets better with time. The dye fades through friction and exposure to the sun, leaving an attractive worn-in appearance that speaks to the fabric’s rough-and-ready workwear origins. This can take months to achieve naturally, but doing it yourself is not the only option, as many denim jackets are stone-washed or otherwise treated to give them that lived-in look before you even buy them. This one has been dyed black and then bleached for an uneven finish that reveals the texture of the denim beautifully.

The toughness of denim meant it was made for the punk rock scene. You could do what you wanted to it – cut it up, stitch it back together, spatter it with bleach or apply patches to it – and it only looked better. As the subculture’s unofficial uniform, the denim jacket has itself become imbued with the spirit of punk over the years. It’s an association designers draw on today when they want to add a little attitude to their designs. See here, for example, how a bleach-splashed, heavily patched denim jacket brings an otherwise low-key outfit to life.

Mixing different dress codes or fabrics is an easy way to have a bit of fun with your outfit and denim, a heritage material with roots in 20th-century workwear, is a natural choice. How about wearing a denim jacket with tailored trousers, for example, or layering one under a nylon bomber jacket? And if you want to take things to the next level, you can try the sort of spliced garments seen at brands such as Sacai or Greg Lauren, in which two jackets of different origins are cut up and stitched together into one great Frankenjacket. Here, the ribbed cuffs and zipped pockets of a late-20th century bomber jacket contrast strikingly with the trademark stitching of a denim trucker jacket.

Perhaps the most recognisable style of denim jacket is the trucker jacket, otherwise known as the Levi’s Type III. (You can distinguish it from the Type II by the darted seams that run down from each of the chest pockets.) An iconic piece of menswear, you really can’t go wrong with one of these, but how do you stand out from the crowd? As illustrated here by Mr Virgil Abloh, it’s all about the fit. Wearing a jacket cropped at the waist over a longer T-shirt creates a fresh silhouette and pairing it with a contrasting colour or pattern – in this case, the camo-print of the trousers – helps the jacket to stand out. We have to mention the watch, too. Gold is a big statement, but Mr Abloh proves it needn’t feel out of place in such a casual outfit. In fact, his willingness to disregard convention – to mix high with low, rugged with sophisticated – epitomises what’s so exciting about modern male dressing.

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