Few garments in a man’s arsenal are more relevant today than the denim shirt. Likewise, few garments have travelled further or transformed over time in quite the same way.

As with its original companion, the Levi’s 501 jean, the denim work shirt was a hard-working, rugged garment, designed entirely for ranchers, cowboys and labourers to put through its paces. It’s a misconception that Levi’s were the first to make the denim shirt, by the way. While they popularised it in large part, they were in fact beaten to the punch by another smaller maker, Miller & Co. who started sewing them thanks to popular demand in the mid-west in the early 1920s. Levi’s followed suit around 10 years later.

But, like so many workwear garments, the shirt’s character changed when the cowboy made it onto the silver screen as a romantic mid-century hero. The strapping figures of John Wayne, Clint Eastwood and Gary Cooper et al were seldom seen without a denim shirt in the mix somewhere; and Spaghetti Westerns propelled the denim shirt from a workwear stalwart to an American cultural icon. It’s enjoyed a comfortable place in the male wardrobe ever since.

While denim shirts are hardly a new phenomenon to classic menswear (I think I bought my first ‘Victoria Denim’ spread collar shirt in 2012, and hell that makes feel old…) the way in which we think about them has changed in recent seasons. Denim dress shirts were all the rage 10 or so years ago, cut in dressy denims with neat spread collars, very much designed to be worn with your back-bladed, four-in-hand knot tie and puffy-shouldered suit. This iteration of denim shirt has grown to be a little predictable these days, synonymous with the ‘Pitti Peacock’ look that we’ve all become so tired of.

Today, the value of a denim shirt lies in the way it contrasts with sleek, understated tailoring. It adds a low-key quality to a sharp suit or separates. I tend to gravitate towards denim shirts cut in a western style, or at the very least with a couple of utility pockets on the chest for this reason. As men’s style evolves, so too does the place of tailoring in our wardrobes, and the casual quality a denim western or work shirt adds to a tweed sports coat and dark flannels feels relevant to today – more so than a denim shirt that’s trying to be smart in a casual fabric.

Naturally, there different schools of thought as to how to care for denim shirts. Some argue that they need only the gentlest, most sympathetic of washes to maintain their original character, partially because the fabric can shrink (although Thomas Mason’s denims are remarkably stable in my own experience) and partially because, as with jeans, any denim shirt will inevitably fade the more it’s washed over time.

I take the view that it’s both futile and a great shame to attempt to perfectly preserve the denim fabrics in your own wardrobe. The joy of denim lies in the way it changes character over time; how it softens and washes down. Any denim shirt will feel a little stiff and starchy at first, but it’ll end up feeling smoother and more comfortable than poplin if you let it do its thing.

I also think the faded lines and puckered seams that start to emerge on denim shirts as they’re washed makes them infinitely more interesting to wear with tailoring than a shirt that’s pristine. With that in mind, once a shirt reaches a certain ‘sweet spot’ in terms of colour and fade, you might like to start hand-washing it, which makes plenty more sense to me than not washing it in the first place.

Thomas Mason has dozens of different denims available for bespoke clients, the pièce de résistance of which is the aforementioned Victoria Denim. This is woven with a 120s two-ply yarn count (unusually fine for a denim fabric), indigo dyed and then washed during the finishing process to produce a wonderfully soft fabric that is easy to interchange with other blue shirts in Oxford or poplin as the mood takes you. Several different colours are available from charcoal, to pure indigo, to soft powder blue. You should have at least one Victoria denim shirt in your wardrobe and enjoy the way that even this pre-washed denim will continue to soften and fade over time.

Other wintry options include Thomas Mason’s Brisbane denim, which is a little heavier for shirts that feel authentically rugged. The brand’s fabric boffins have also perfected a linen denim that’s perfect for spring and high summer. Called Alassio, this collection offers a few different indigo-dyed cloths in different shades with a soft melange texture to them – ideal for smart or casual warm weather dressing and very cool to wear.

All of which goes a long way to saying that a denim shirt is far from homogenous and playing with weights, cuts and washes will pay dividends. And, if you’ve yet to try a denim western or workwear shirt with suiting, perhaps now is the time.