There are certain wardrobe truths that never really change with the seasons: a well-chosen pair of trousers, a jacket that actually fits, and at least one—honestly, more than one—button-up shirt. As much as we love the humble white tee, 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 to throw on with jeans and a blazer when the occasion calls for something between casual and dressed-up.

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 small styling decisions that make each look work. From tailoring that feels intentional rather than obligatory to relaxed beach layering and the return of easygoing flannel, these looks prove just how versatile a button-up can be.

Here are 5 ways men are styling button-up 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 menswear’s stuffiest getup. There are moments when a suit is the only appropriate option, and there are also many more moments when you could wear one and simply choose not to. Both of those are worth reconsidering.

Pairing button-up shirts for men with a suit sounds like basic knowledge, and in theory, it is. But the number of guys walking around in skin-tight fits with stretchy cut-away collar shirts suggests otherwise. The fix is actually simple: go back to classic tailoring. Not boxy, not painted-on, just well-proportioned. A navy or charcoal suit in a traditional fabric, a white or light blue poplin shirt, and a simple tie. That’s your foundation.

From there, the personality comes from the details around it. A Bogart-esque trench coat. A pair of interesting sunglasses. A gold earring or a standout watch. The idea is simple: keep the shirt and suit traditional so the surrounding elements can have a little fun. Once you begin to see a suit as a canvas rather than a uniform, the entire look clicks.

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#2. With a Tank Top Underneath — Layered, Not Lazy

Wearing a tank under your button-up can be purely functional: extra coverage in formal settings, sweat protection when it’s blazing out, a little warmth when the A/C is going full blast. But it can also look genuinely cool, provided you do it right.

The first move is to leave the overshirt completely unbuttoned. A relaxed linen or Oxford shirt worn open over a simple white tank is one of the easiest outfits a man can put together. There’s an inherent James Dean energy to it that reads effortless rather than try-hard. If your style runs bolder, a silky or textured underlayer works too. The practical upside is that you can peel the overshirt off when things heat up and still look like you dressed with intention.

The second option is leaving a few buttons undone so the tank just barely peeks through at the collar. It’s subtler, a little more playful, and works especially well in warmer months. Don’t go too far down; the line between effortless and contrived is thinner than it looks, but a button or two makes a real difference in how relaxed the neckline feels.

From the waist down, jeans are the easy choice. High-waisted slacks push the whole thing in a slightly sharper direction. A low-profile sneaker or a dressier cowboy boot works well with either, depending on how dressed up you want to look.

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#3. Denim on Denim — Lean Into the Commitment

A denim button-up has a kind of range that’s easy to underestimate. The hard-wearing classic is inherently easygoing, but depending on the silhouette and wash, it can slot in cleanly alongside tailoring. The most interesting way to style it is to lean into both of those qualities at once.

The denim-on-denim approach requires a little nerve, 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 tailored overcoat, or anything with a clean silhouette. That contrast between the ruggedness of the denim and the refinement 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 is loud. Together, they make the outfit feel deliberate. And notice how the outerwear (the sleeker, more polished piece) does the heavy lifting when it comes to pulling everything into focus.

If you want to take it in a more casual direction, swap the trench for a leather bomber, add a baseball cap, and the vibe shifts completely. Same foundation, different energy. That’s the beauty of it.

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#4. A Flannel Shirt — Worn Without Care

Flannel hasn’t been on-trend since the hipster lumberjack era, and it wasn’t particularly cool long before that either. But here’s what most men are missing: that’s actually the point. Button-up shirts for men made from brushed cotton flannel are best worn exactly the way our fathers’ generation wore them—without overthinking it, without trying to make them into something they’re not.

Flannel is a great at-home fabric. It’s a great weekend-chores fabric. It’s a great “I want to wear something that’s not a T-shirt” fabric. 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 straightforward: wear it under a bomber jacket for a look that’s been working since at least the mid-century, or swap the bomber for any other outer layer, and you’ll find it still holds up. With trousers, it reads more intentional. With jeans or cargos, it reads more relaxed. The thing about flannel is that neither of those outcomes requires much decision-making on your part. You really can’t go wrong, and that kind of wearability 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 part of what makes it interesting. Menswear has gotten notably sexier in recent years: tighter, sheerer, shorter, and the button-up has been pulled along with it. The shirt-and-short-shorts combination is a look that requires a specific kind of confidence, but for men willing to fully commit, it pays off.

Think breezy, elastic-waist cotton shorts, the five-inch inseam variety, paired with a relaxed button-up shirt worn open or loosely tucked. Crew socks and clean sneakers seal the deal. Consider loafers if you want to push it in a slightly dressier direction. The beach is the natural habitat for this look, but it works anywhere warm and casual: a weekend market, a low-key outdoor restaurant, a backyard gathering.

The catch is that half-measures don’t work here. If you’re going to wear a button-up with short shorts, you have to actually wear it—with conviction, with a shirt that fits well, with shorts that aren’t trying to be something else. The guys who pull this off aren’t doing it reluctantly. They’re doing it because they decided to, and that decision reads. So if you’re considering it, start hitting the squat rack now. Beach season doesn’t wait.

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The Real Flex Is Knowing How

What all of these looks share is that the button-up is never just a button-up. It’s always in conversation with something—the jacket over it, the layer beneath it, the trousers below it, the accessories around it. That’s what makes styling button-up shirts for men worth taking seriously. The shirt itself might be the starting point, but the outfit is everything that happens next.

Get the fit right, choose a fabric appropriate for the occasion, and then make one deliberate decision about how to style it. That’s really all it takes. The rest sorts itself out.

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