How to Style a Denim Shirt for Men: 8 All-Season Outfit Ideas

How can a man wear a denim shirt all year without it feeling forced?

There’s a certain no-nonsense charm to a denim shirt. It’s not flashy. Doesn’t try too hard. But wear it right and it slots into just about any outfit across the seasons. The trick isn’t reinvention, it’s choosing the right pairings. Get the wash, fabric weight and fit sorted, and the rest sorts itself. Whether it’s early spring or the tail end of autumn, a well-fitted denim shirt always pulls its weight.

Why does a denim shirt keep showing up in every man’s wardrobe?

Honestly? Because it works. That’s about it. It’s durable, feels like proper clothing, it’s not something delicate or disposable and unlike most shirts, you don’t need to iron it every time it hits the wash. Denim fabric has that twill weave. Tough, structured. It holds shape. And the more you wear it, the better it looks. Just like a good pair of jeans.

Now, some shirts come in featherweight chambray or brushed cotton. But denim? Real denim carries its weight. You’ll feel the difference when you put it on. It’s solid. And if you’ve got a rotation of jackets, cords or chinos, it’ll slip right in.

Western or workwear: does it really matter?

A bit. Mostly in terms of the vibe you’re after.

• Western-style denim shirts are the ones with those pointed shoulder seams, press studs, and two chest pockets. If you’re picturing a bloke on horseback in New Mexico, you’re not far off.

• Workwear shirts keep things more understated. Flat seams, regular buttons, sometimes only one chest pocket. They’re easier to dress down, or up, depending on how clean the rest of your outfit is.

If you’re just after one solid shirt to wear different ways? Go with a medium or dark wash workwear version. Fewer bells and whistles. Easier to build outfits around.

Alright, how do you actually wear it?

1. With canvas trousers and proper boots

This one’s straightforward. You take a midweight denim shirt, pair it with canvas trousers that are olive, tan and finish with leather boots. Solid. No fuss.

Canvas is rougher than chinos but smoother than denim. That contrast helps. You’re not doubling up on textures or looking too uniform. If you’ve got a brown belt and some field boots, even better.

And for brands? Taylor Stitch, Carhartt, or even some old Dickies if you want looser fits. The key here is fabric weight. Don’t pair a thick denim shirt with paper-thin trousers. It throws the whole thing off.

2. Joel from The Last of Us nailed it

You’ve seen the look. Worn denim shirt, dark jeans, tan waxed cotton jacket. Boots that look like they’ve done actual work. It’s grounded and sort of unbothered, but still looks right.

It works because the shirt isn’t trying to be flashy. It’s faded. Lived in. And the canvas jacket adds just enough structure without turning the whole outfit into costume.

Try this in autumn or on cold spring mornings. It’s the sort of outfit that doesn’t care what anyone thinks. That’s half the charm.

3. With chinos when you want to look sharper

Got a casual date? Quick meeting? Lunch out? A denim shirt with slim chinos does the job. Navy shirt and beige chinos is the classic move, but charcoal, olive or even rust works too.

You don’t need to tuck it in, but if you do, go for a proper leather belt. Tidy boots or suede loafers finish it off. It’s the sort of smart casual that doesn’t overpromise but never looks underdressed.

Fielding and Nicholson’s cut of chinos, for example, keeps things fitted but breathable. No pinching at the thighs. No gaping at the waist. It’s rare.

4. With black jeans and white trainers

If you’ve got no idea what to wear, this’ll do it. Denim shirt over a white tee, black jeans, white trainers. Done.

It’s the closest thing to a safety net in menswear. Works across ages. Works across seasons. If it’s cold, chuck on a black leather jacket or a bomber. If it’s warm, roll the sleeves up.

Just don’t wear this with an overly styled denim shirt — no frayed hems or contrast stitching. Keep it clean. That’s what makes it modern.

5. Corduroy trousers in the mix? Yes, please.

Corduroy’s one of those fabrics people forget about until autumn hits, then everyone remembers how good it feels. And it pairs surprisingly well with denim.

A dark denim shirt with brown or forest green corduroys feels a bit vintage but not dated. Add in some leather chukkas or suede trainers. That’s it.

This is also the look that quietly tells people you know what you’re doing, without having to say anything.

6. Shorts in summer, but pick the right ones

Not every pair of shorts will work. If they’re too flimsy, like linen or polyester blend gym shorts, forget it. Denim’s weight needs balance.

Go for tailored cotton shorts in stone, navy or muted green. A lighter wash denim shirt works best here. Keep it unbuttoned over a vest or clean tee. Trainers or slip-ons round it out.

If you’re sweating just reading this, roll the sleeves up and undo another button. Sorted.

7. With white or ecru jeans for a cleaner look

White jeans aren’t just for yacht parties or weddings abroad. A light blue denim shirt with off-white or ecru jeans looks easy and deliberate. Add tan loafers or neutral trainers and it becomes a solid spring outfit.

And yes, you might get a bit of grief the first time you wear white jeans. Doesn’t matter. They look great if they fit right.

8. Go smarter with a tweed jacket

This one leans heritage, but done right, it’s sharp. A dark wash denim shirt under a brown or grey tweed sports coat, with wool trousers or slim chinos. Suede Chelsea boots on the feet.

It’s the kind of thing Ralph Lauren’s been pushing for years, and for good reason. It makes you look put-together without wearing a tie or suit. Bonus points if your denim shirt has no chest pockets — keeps things cleaner.

Anything to avoid?

Oh, plenty.

Do

• Mix fabrics that balance: denim with canvas, corduroy or wool

• Keep your washes subtle: dark and mid wash are your friends

• Think about contrast: colour and texture both matter

• Wear footwear that matches the weight of the outfit

Avoid

• Denim on denim unless the washes are clearly different

• Overly distressed or bleached shirts unless you’re going full vintage

• Shiny shoes with a denim shirt. It just looks mismatched

• Shirts with massive logos or embroidery — they date fast

One last thing

A denim shirt isn’t here to impress. It’s not flash. But that’s exactly why it works. You wear it, wash it, wear it again. It settles into your wardrobe like it’s always been there. And when you get the hang of pairing it with textured fabrics, neutral colours and the right footwear, you stop overthinking.

And if it fades a little? Good. That means it’s doing its job.