Mens Denim Shirt: Ways to Wear It

I was sitting on my bedroom floor at like eleven at night surrounded by every piece of clothing I own because I was supposed to be filming a “closet cleanout” video and instead I was just building increasingly weird piles. Keep pile. Donate pile. The pile I labeled “why do I own this” which was mostly graphic tees from 2019. And then I pick up this denim shirt I forgot I even bought, medium wash, kind of a western yoke on the front, tags still half attached because I wore it once to my brother Marcus’s birthday thing and then it went into the void of my closet for like eight months.

And I put it on over the tank top I was already wearing, just to see, and I looked in the mirror and went okay wait.

Wait actually. This is doing something.

Here’s my thing with denim shirts, and I need you to know I’m saying this as someone who spent a genuinely embarrassing amount of time thinking they were a dad thing. Like a “I’m going to a barbecue and I also might mow a lawn later” garment. My assumption was tucked in, maybe with a bolo tie situation, definitely with boots that have seen a horse. And some guys absolutely do wear it that way and honestly, respect, but that’s not the only setting this thing has. That’s like saying jeans only come in one fit. We all know that’s not true anymore, we all had that reckoning already.

What actually happened is I started noticing it everywhere once I put mine back into rotation. On guys getting coffee looking effortlessly thrown together in a way that was clearly NOT effortless, don’t lie to me, that took planning. On a guy in a street style video that hit my For You page four separate times in one week, which at this point I take as a sign from the algorithm itself. The denim shirt is having a moment where it’s shaking off the dad energy and turning into something that photographs really well, layers really well, and covers about six different vibes depending on what you put with it.

So I want to actually go through the ways I’ve seen this work, and the one way I tried that did not work, because we’re being honest here, that’s the whole deal.

[Men’s Denim Shirts]

The Double Denim Thing, Done on Purpose

Okay so double denim. I know. I KNOW the instinct is to run. For years the rule was one piece of denim per outfit, that was just law, nobody questioned it. And then somewhere in the last year or two it flipped completely and now doing it on purpose, denim shirt with actual jeans, is the whole point.

The trick, and I learned this the hard way after posting a fit that got exactly one skull emoji reaction in my group chat and zero words, is contrast in the wash. Same wash top and bottom just reads like you got dressed in the dark, or like a uniform, like you’re about to hand someone their car keys back at a valet stand. What actually works is a lighter wash shirt with darker, almost black jeans, or the reverse, a dark shirt over lighter denim. The contrast is what makes it look intentional instead of accidental.

I did this with a chore-coat style denim shirt, left it open, white tee underneath, black jeans, white sneakers, and filmed it for a “outfits that don’t try too hard” video and it did numbers I genuinely was not expecting. Comments were like “wait this actually goes” which, rude, but also fair, because I wasn’t expecting it either the first time I put it together.

The failed take, because there’s always one, was me trying the exact same wash top and bottom with cowboy boots thrown in for good measure. I looked like I was in a very specific kind of music video from 2011. Deleted the footage. We do not speak of it.

[Double Denim Looks]

Layering It Like It’s an Extra Jacket

This is the one that made me actually reach for mine again and again once the weather started doing that thing where it’s cold in the morning and then somehow eighty degrees by 2pm, which, Austin, thanks for that. A denim shirt worn open over a plain tee functions basically as a light jacket, and it’s the move I go back to more than almost anything else in this whole piece.

Under a bomber or a canvas overshirt it adds this little peek of collar and texture that reads way more put together on camera than a plain crewneck ever does, I’ve tested this, I filmed the same outfit two ways for a video and the version with the denim shirt underneath got noticeably more comments about “the fit” specifically. Camera doesn’t lie, that’s basically my whole professional philosophy at this point.

It also solves the problem of temperature swings without you having to actually carry a jacket around like some kind of responsible adult. Sleeves down and buttoned when it’s cold at 8am, sleeves rolled and shirt open by noon, tied around the waist if it gets truly unreasonable, though I’ll be honest that last one works better on women’s fits, on a guy it can read a little bit like you’re about to start a pickup soccer game. Your call.

[Layered Denim Shirts]

Making It Look Dressed Up Without Actually Trying That Hard

This is the section for the guy who has a dinner reservation or a work thing that says “smart casual” on the invite, which is genuinely the most stressful two words in the English language, nobody actually knows what that means.

Denim shirt, tucked, into chinos or dark trousers, with a leather belt and actual shoes instead of sneakers, and suddenly the whole thing reads dressed up without being a button down and blazer situation. I’ve seen this done with a slightly darker, almost indigo wash shirt that basically photographs like a solid navy from a few feet away, which is doing a lot of the smart casual heavy lifting honestly, nobody clocks it’s denim until they’re standing right next to you.

Add a blazer over it, and this is the part that surprised me, it does not look like a mistake. It looks like someone who owns a blazer and also has a personality, which is rarer than it should be. I sent a photo of this exact combo to the group chat before I’d even taken it off and one person said fire, one person asked if I was going to a wedding, and honestly both reactions were correct depending on which wedding.

Where I’d stop is a full suit situation, that’s a bridge too far, the denim shirt wants smart casual, it does not want to be mistaken for a dress shirt in actual formalwear, it will lose that fight every time.

[Dressed Up Denim Shirts]

Black Denim, For When You Want an Edge

Light wash denim shirts have this built in easygoing energy, they just do, there’s no getting around it. Black denim is a completely different personality and I did not appreciate that distinction until I bought one on a whim during a very specific three week period where I was apparently only capable of wearing black, don’t ask, it was a whole phase.

A black denim shirt worn with black jeans and white sneakers is one of those looks that reads intentional and slightly edgy without you doing anything else, the monochrome is doing all the work. It photographs INCREDIBLY well too, which is a genuinely useful thing to know if you’re someone who takes more pictures of your outfits than you’d like to admit to your family group chat.

Where it gets more adventurous is layering it under a denim jacket in a different wash, texture on texture, tonal but not matching, which sounds like a lot and honestly the first time I described this to a friend she just said “so you’re wearing two jackets” and I said kind of, yes, and she said okay and walked away, which felt like the correct amount of skepticism.

It also just works with a plain white tee underneath and boots, that’s basically the low effort version and it still looks like you thought about it for longer than the ninety seconds you actually spent.

[Black Denim Shirts]

Rolled Sleeves, Shorts, and the Whole Summer Version

I almost skipped this one because I assumed a denim shirt was strictly a fall thing in my head, cooler weather, layering season, all that. And then I saw it worn short sleeved, or long sleeved but rolled properly to the elbow, with actual shorts, chino shorts specifically not athletic ones, and sandals or clean white sneakers, and it completely reset how I thought about the season this thing belongs to.

This is genuinely the easiest formula in the whole piece. Shirt, shorts, done, you don’t need a third piece, you don’t need to think about layering, you just need the sleeves rolled correctly which is the one detail that separates looking put together from looking like you just got hot and gave up. Roll from the cuff, not from the shoulder, fold it twice, that’s it, that’s the whole secret.

I tried this look for a beach town trip video and it held up through an entire day of walking around in ninety degree heat, one iced coffee spill directly onto the sleeve which wiped off completely fine because denim just does that, and one accidental sprint to catch a ferry, and it still looked like a shirt at the end of it rather than a damp rag, which honestly is more than I can say for half the linen stuff I packed on that same trip.

[Summer Denim Shirts]

Final Thoughts

If you’d told me a year ago I’d end up writing over two thousand words defending the denim shirt I genuinely would have laughed, sorry, that’s the honest reaction. It sat in my closet with the tags half on for eight months because I had this one fixed idea of what it was for and I just never bothered to test it against literally any other setting.

What actually changed my mind was just putting it in different situations and watching what happened. Over a tee it’s a jacket. Tucked into trousers it’s dressed up.

Paired with matching denim on purpose it’s a whole statement instead of an accident. In black it’s got an edge I did not expect from a fabric I associated with barbecues. With shorts it’s somehow a summer piece, which broke my brain a little.

The common thread, if there is one, is that this shirt does more when you stop treating it like a costume piece for one specific occasion and start treating it like the thing underneath, or over, or tucked into everything else. It’s not trying to be the main character in every outfit, and honestly that might be exactly why it works in so many of them.

Anyway. Mine’s back in the keep pile. Obviously.