Men’s Denim Shirt Outfit Inspiration: 14 Stylish Looks For 2023
A denim shirt brings a rugged, masculine feel to any outfit. Here's how to wear this Americana classic, for both smart and casual occasions.
Evoking classic Americana, from the gold miners and cowboys of the early 20th century to iconic images of Steve McQueen and Elvis, the denim shirt is a menswear classic. Transcending its humble origins to become a modern-day wardrobe staple, it’s a rugged garment that’s just as at home under a tailored suit in the office as it is with chinos in the pub.
But which denim shirt is right for you? There’s a huge variety on the market today – from classic western designs through to sleek, formal styles – so read on to discover the key types of denim shirts you should be considering, and how to wear one for a number of different occasions.
Key types of men’s denim shirts
It might not be your first choice for a dress shirt, but lightweight denim makes for an excellent alternative to more pedestrian, traditionally smart fabrics like cotton poplin. Denim has bags of texture, adding visual interest to all manner of tailoring, from sharp double-breasted lounge suits through to unstructured, Italian-style blazers.
Of course, the fabric is known for its extensive use in casualwear, and as such will add a dressed-down feel to your attire, so keep this in mind if you plan to try it at work (we don’t recommend turning up to a board meeting in one). If the dress code is formal then it’s best given a wide berth, but for smart casual or business casual settings it’s ideal.
When it comes to the style of shirt, look for one cut in much the same way as an Oxford shirt: a tailored cut, a single (or no) chest pocket and a button-down collar. It will be relaxed enough to wear on its own with a pair of tailored trousers, yet smart enough to combine with your finest suit.
While very much associated with the American West, hence the name, the western shirt actually has origins in Mexican and Native American styles of dress. The versions you know are traditionally made from light- to mid-weight denim, and were favoured by cowboys and miners at the turn of the 20th century who adopted them for their hardy, durable design and practical chest pockets.
The style has since been worn by everyone from John Lennon to Steve McQueen, and is somewhat of a wardrobe staple. Casual leaning, a western shirt is incredibly easy to wear but looks its best teamed with similarly rugged, blue-collar clothing – think traditional workwear such as chore jackets, carpenter pants, moc toe boots, selvedge denim and the like.
Utilitarian work shirts
The western shirt may be what you instantly picture when you hear the words ‘denim shirt’, and they certainly evoke somewhat of a vintage charm. But for something more contemporary in look and feel, you might want to consider its modern incarnation.
Utilitarian denim work shirts take inspiration from the centuries-old silhouette, but trim back the extraneous details somewhat. The rear yokes, contrast stitching and flap pockets of the western shirt are done away with in favour of simple open chest pockets and a boxier fit that makes them easy to layer.
How to wear a denim shirt: things to consider
Of course, there are many varying types of denim to suit a wide array of tastes and needs. So, when choosing a shirt, given that it’s the defining feature, it’s best to at least think about what kind of fabric you’re looking for.
Do you want something incredibly hardwearing and durable, that will take on a unique patina over time? Raw denim is for you. After something a bit softer that will be comfortable straight off the rack? You should consider stretch denim. Want a shirt that won’t ruin the lines of your tailored suit? Seek out a lightweight denim or chambray blend.
How it fits
The question of fit is always of great importance with shirts. But more than just feeling good on, fit also dictates how formal or casual it looks.
With a smarter shirt, you’ll want something that’s tailored to your body and cut slim so you can tuck it into a pair of trousers or chinos. However, avoid anything too tight that pulls across the chest or back (the buttons straining is a dead giveaway) – you want a shirt that helps shape your torso and yet feels comfortable as you go about your daily business.
Off-duty denim shirts often look best in a boxy cut. This gives them a more relaxed feel and better suits a style of shirt that’s worn untucked or even unbuttoned over a T-shirt. Not only that, it makes it easier for layering, too – enabling it to slot underneath a heavier jacket or coat in winter.
Colour or wash
Naturally, denim is most often found in blue shades. From raw, dark indigo through to pale washes, a blue denim shirt is an easy sell, and one that’ll effortlessly slot into any contemporary wardrobe.
That said, don’t discount other shades. A black denim shirt is an incredibly versatile option, whether you choose to wear it as part of an all-black look or with more natural shades like stone, green or brown.
Then there’s off-white. An interesting, summer-ready choice that works especially well on utilitarian designs, an off-white denim shirt is a blank canvas that combines well with tailored trousers, chinos or even shorts on those cool August evenings.
Men’s denim shirt outfits
The easiest way to wear a denim shirt with tailoring? A tonal blue palette. This dark navy, textured wool suit complements the smart mid-blue denim shirt perfectly, while a pair of brown suede Chelsea boots finishes things off in gallic style.
The French-style work shirt is a classic, although it usually comes in a mid blue, heavyweight cotton. Find one in denim and you’ve got a more individual take, which works well with lighter shades like off-white and cream.
Layered up denim shirt
A simple, lightweight denim shirt is an ideal layering piece for fall. Find one with a slim fit that works tucked in, and combine it with a padded gilet and cargo pants for a lumberjack-inspired, functional take on cold-weather dressing.
Grey is an underrated denim shirt colour. Muted and understated, it casually and stylishly finishes off a double denim look of black jeans, white tee and sleek Chelsea boots, as proven here.
The denim Oxford shirt
If you’re limited to purchasing just one denim shirt, you may as well make it a button-down. As versatile as an Oxford shirt but with a bit more flair, the denim button-down works with casualwear, but also looks good tucked in to an unstructured suit, giving you the most bang for your buck.
Denim shirts aren’t just for formal heads or workwear nuts. It’s also a staple of the streetwear community and looks great paired up with logo caps, chunky sneakers and relaxed-leg pants. For the latter, keep the fit tapered and not too baggy and you’ll be on to a winner.
The modern western shirt
Western shirts can appear a little old fashioned. But find one with slightly more angled, minimal design details and it’ll look as modern as any other shirt in your rotation. Wear it with black jeans and retro runners and you’ve got an adaptable look that’s ideal for weekend drinks.
Denim shirt and shorts
For the warmer months, a lightweight denim shirt is a great alternative to cotton or pique. Go for one in an off-white shade and combine it with tailored shorts for a simple, spring or summer outfit.
Keep it light (wash)
Dark indigo work shirts are undoubtedly a safer option, but light, bleached washes are infinitely cooler. Thanks to extensive washing the denim will likely be super soft off the rack, and have already shrunk too, making this a great option if you’re concerned about fit.
When it comes to styling, throw it on with equally pale shades, as well as lighter greys and white, to create effortless warm-weather ready looks like this.
All-black attire will always be cool. The go-to choice of Johnny Cash and Paris’ Left Bank in the 60s, it’s ideal for days that turn into long nights on the town. Black denim shirts slot into the look seamlessly, especially if combined with relaxed-fit chinos and black leather Chelsea boots.
Black and white (denim)
If you’re stuck on how to wear a white denim shirt, combining it with black is always a safe bet. Try a white denim work shirt with wide-legged black chinos and white minimal sneakers, and you’ve got a slick, street-ready look that requires minimal effort.
Swap the jacket
The versatility of the denim shirt is proven when you consider its potential as an outer layer. In many cases it negates the need for a lightweight jacket, thanks to its hardy fabric and (usually) dense weave, which works to keep you warm.
Throw it on over the top of tees, hoodies or fine-gauge sweaters when you need to take the chill off.
Such is the prowess of denim, it also works in short sleeve, Cuban collar form. As long as the fabric is light and relatively breathable (think a chambray blend), a denim shirt of this nature is an excellent alternative to more traditional summer fabrics like cotton and tencel.
Wear yours with white trousers and finish with loafers for a sophisticated vacation-ready look.
Classic country suiting typically consists of bold check suits and fusty corduroy or flannel shirting. While a tweed suit can look cool, these traditional, old-fashioned shirts often let them down. This is where denim comes in. With its more utilitarian look and feel, a denim shirt can inject a bit of life in country wear.
So, if you’re looking to rock a check suit on the estate, don’t be afraid to give it a try.
Khaki and blue
It might be the fact that it’s widely associated with preppy attire, but a blue shirt and khaki pants combo has somewhat of a classic, Americana feel to it that we can’t get enough of. Endlessly versatile, try updating this Ivy League go-to with a denim shirt, basketball shoes and a beanie, for a streetwear twist.