There are certain clothing truths that never really change with the seasons: well-chosen pants, a jacket that actually fits, and at least one—honestly, more than one—button-up shirt. As much as we love the simple white T-shirt, button-up shirts remain the cornerstone of a solid men’s wardrobe. You need one for the office. You need one to wear with a tuxedo. And you need one that you can wear with jeans and a blazer when the occasion calls for something between casual and dressy.
The shirt itself, however, is the easy part. Knowing how to style it is what separates a good outfit from a great one. With that in mind, here are the best ways men are wearing button-up shirts in 2026, and the little styling decisions that make each look work. From tailoring that feels conscious rather than obligatory, to relaxed beachwear and the return of easy flannel, these looks prove just how versatile a button-up can be.
Here are 5 ways men style button-down shirts, and some of the best on the market right now…
#1. With a suit – but make it feel like a choice
We don’t care what you think about the dirtiest menswear outfit. There are times when a suit is the only right option, and there are also many more times when you could wear one and simply choose not to. Both are worth reconsidering.
Pairing men’s shirts with a suit sounds like basic knowledge, and in theory it is. But the number of guys walking around in figure-hugging fits and shirts with stretch-cut-away collars suggests otherwise. The solution is actually simple: go back to classic customization. Not angular, not painted on, just well proportioned. A navy blue or anthracite suit in a traditional fabric, a white or light blue poplin shirt and a simple tie. That is your foundation.
From there, the personality comes from the details surrounding it. A Bogart-esque trench coat. Some interesting sunglasses. A gold earring or a striking watch. The idea is simple: keep the shirt and suit traditional so that the surrounding elements can have a little fun. Once you start thinking of a suit as a canvas instead of a uniform, the whole look clicks.
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#2. With a tank top underneath – layered, not lazy
Wearing a tank top under your shirt can be purely functional: extra coverage in formal occasions, protection from sweat when it’s hot, a little warmth when the air conditioning is on full blast. But it can also look really cool, if you do it right.
The first step is to leave the overshirt completely open. A relaxed linen or oxford shirt worn open over a simple white tank top is one of the easiest outfits a man can put together. There is an inherent James Dean energy that reads effortlessly rather than trying hard. If your style is bolder, a silky or textured underlay also works. The practical advantage is that you can take the overshirt off when it gets warmer and still look like you’re dressed on purpose.
The second option is to leave a few buttons open so that the tank top barely peeks through the collar. It’s more subtle, a little more playful and works especially well in the warmer months. Don’t go too far down; the line between effortless and contrived is thinner than it seems, but a few buttons really make a difference in how relaxed the neckline feels.
From the waist down, jeans are the easy choice. High-waisted trousers push things in a slightly sharper direction. A low-key sneaker or a dressier cowboy boot will go well with either, depending on how dressed up you want to look.
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#3. Denim on denim — Lean into the promise
A denim button-up has a reach that is easy to underestimate. The hard-wearing classic is naturally easy-going, but depending on the silhouette and wash, can work beautifully with tailoring. The most interesting way to style it is to lean on both qualities at once.
The denim-on-denim approach takes some guts, but when it lands, it really lands. Start with a denim shirt and jeans in a similar wash, not necessarily matching, but within the same color family. Then balance the casual weight of the double denim with something polished on top: a structured trench coat, a fitted overcoat or something else with a sleek silhouette. That contrast between the robustness of the denim and the sophistication of the outerwear is exactly what makes the look work.
Accessories help bridge the gap between the two worlds. Think Wayfarer-style sunglasses, a simple gold chain or a Western belt. Individually, none of these are loud. Together they ensure that the outfit feels well considered. And notice how the outerwear (the sleeker, more polished piece) does the heavy lifting when it comes to framing everything.
If you want to take it in a more casual direction, switch up the trench coat a leather bomberadd a baseball cap and the atmosphere changes completely. Same base, different energy. That’s the beauty of it.
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#4. A flannel shirt – worn without care
Flannel hasn’t been in fashion since the hipster-lumberjack era, and it wasn’t particularly cool long before that. But here’s what most men miss: that’s actually the point. Men’s button-up shirts, made from brushed cotton flannel, are best worn exactly as our fathers’ generation wore them – without thinking about them, without trying to make them into something they are not.
Flannel is a great fabric for the home. It’s a great fabric for weekend chores. It’s a great one “I want to wear something that isn’t a T-shirt” dust. The texture is warm and lived-in, the weight is satisfying, and the plaid patterns do most of the visual work without any effort on your part.
Styling it is simple: wear it under a bomber jacket for a look that’s been working since mid-century, or swap the bomber jacket for another outer layer, and you’ll find it still holds up. With pants it reads more deliberately. With jeans or cargo pants it reads more relaxed. The thing about flannel is that neither of these outcomes require much decision-making on your part. You really can’t go wrong, and that kind of portability is rarer than it sounds.
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#5. With (short) shorts — if you’re willing to commit
This one isn’t for everyone, and that’s what makes it interesting. Men’s clothing has become noticeably sexier in recent years: tighter, more transparent, shorter, and the button closure has moved along with it. The shirt and shorts combo is a look that requires a specific kind of confidence, but for men who are willing to fully commit, it’s worth it.
Think of airy cotton shorts with an elastic waist, with an inseam of 15 cm, combined with a relaxed shirt with button closure, worn open or loosely tucked in. Crew socks and clean sneakers complete the deal. Consider loafers if you want to make it a little dressier. The beach is the natural habitat for this look, but it fits anywhere that’s warm and informal: a weekend market, a quiet open-air restaurant, a backyard gathering.
The problem is that half measures don’t work here. If you wear a button-up with short shorts, you should actually wear it – with conviction, with a shirt that fits well, with shorts that don’t try to be anything else. The guys who make this happen don’t do it reluctantly. They do it because they have decided to do so, and that decision reads. So if you’re thinking about it, start with the squat rack now. The beach season doesn’t wait.
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The real flexibility is knowing how
What all these looks have in common is that the button-up is never just a button-up. It’s always in conversation with something: the jacket over it, the layer underneath, the pants underneath, the accessories around it. That makes styling button-up shirts for men worth taking seriously. The shirt itself may be the starting point, but the outfit is everything that happens next.
Get the right fit, choose a fabric that’s appropriate for the occasion and then make an informed decision about how to style it. That’s really all it takes. The rest will take care of itself.
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