So I remember the first time I actually put one of these on, a Cuban collar shirt and I genuinely had no clue what I was doing with it. I buttoned the whole thing up like it was a normal shirt, tucked it in, stood in front of the mirror and just stood there wondering why it looked so off. Turns out that’s literally the one thing you’re not meant to do with it. The whole point, apparently, is that open collar just sitting there flat against your chest, not doing up all the way, not trying to look formal at all.
Once I stopped treating it like some kind of dress shirt and just let it be what it is, it all made sense and I’ve been wearing them properly ever since.
That’s kind of what a Cuban collar shirt for men is about, if you think about it. It’s not really a boardroom thing and it’s not trying to be one either. It sits in that weird in-between space, casual, but not sloppy either and once you actually get how it works, it becomes one of those shirts you end up reaching for more than you’d expect.
What Is a Cuban Collar Shirt Anyway
Right, so basically it’s a short sleeve button-up with that flat, open collar that just lies there against your chest, no stiffness to it, no need to do the top button up at all. In India and a lot of Asia generally, people just call it a half sleeve Cuban collar shirt instead, same shirt though, just a different way of saying it depending where you are. You’ll also hear it called a camp collar shirt or a revere collar, sometimes a bowling shirt or a cabana shirt and honestly some shops even list it as a flat collar shirt, it depends entirely on where you’re buying it from. I’ve even seen it listed as a guayabera shirt in a couple of places, which technically is the older, more traditional version of more or less the same idea. So yeah, same shirt, loads of different names depending on the shop and the region.
Most of the ones I own are linen or cotton, mainly because both breathe properly, which is probably why you see this shirt everywhere the second it gets warm. Solid colours, stripes, tropical prints, all of it works really, just depends how loud you’re feeling that day.
If you’re still working out where this actually fits in with the rest of your wardrobe, it helps to know the basics first, I think. I went through the different types of shirts men wear a while back and the Cuban collar is genuinely one of those shirts that earns its own spot rather than just being some variation of something else you already own.
Cuban Collar vs a Regular Shirt
| Feature | Cuban Collar Shirt | Regular Button-Down Shirt |
| Collar Style | Flat, open collar | Standing collar with pointed tips |
| Neckline | Always open by design | Buttoned up or worn with a tie |
| Formality | Casual to smart casual | Casual to formal, depends on fabric |
| Best Season | Warm weather | Works all year |
| Common Fabrics | Linen, cotton, silk blends | Oxford, poplin, twill, flannel |
| Sleeve Length | Mostly short | Short and long |
| Tie Compatible | No | Yes |
| Overall Look | Vacation, resort, easy | Classic, office, everyday |
Really the whole difference comes down to that collar, when you think about it. One’s built to be worn open and relaxed, the other’s built to go up against a tie and a jacket and honestly neither is better than the other, they’re just doing completely different jobs.
A Bit of Where It Truly Came From
So this shirt goes back to the mid-1900s apparently, worn originally by field workers across Cuba who just needed something light for the heat. The open collar wasn’t really a style choice at first, it was just practical, same with that loose, boxy fit, since a shirt that skims you instead of hugging you breathes way better. Resort culture picked it up in the fifties and sixties and it just never really went away after that.
It’s had a few quiet comebacks since, showing up on runways, disappearing, then turning up again in high street shops. Which is honestly proof enough it’s not really a trend, just a shirt that keeps making sense.
Best Pants to Wear With It
With Trousers
I like pairing mine with grey or navy trousers when I want it to look a bit more put together, without going full shirt and tie territory obviously. Works well for dinners or even a relaxed office day if that’s your kind of workplace.
With Chinos
This is probably the one I reach for the most if I’m honest, khaki, olive, navy, whatever, it just works. It’s the combination most people end up searching for anyway because it’s basically zero effort for daily wear.
With Shorts
Tailored shorts, sitting just above the knee, this is your beach or holiday combination really. Actual swim shorts work too, if you’re somewhere near water and want to go straight from the pool to lunch without bothering to change. If the shirt’s already got a print on it though, keep the shorts plain, otherwise the whole outfit ends up fighting itself.
With Jeans
Dark or light wash, straight or slim, keep it simple basically. I made the mistake once of pairing a printed one with distressed jeans and it just looked like two completely different outfits arguing with each other, if that makes sense. Keep the jeans clean and let the shirt do the talking.
Tucked In or Not
Untucked is the default really and honestly the easier option too, it keeps the whole thing relaxed and lets the length of the shirt do what it’s meant to do. Tucking it in works as well, especially with trousers, but it changes the whole feel of it, more put-together, less beachy I suppose. If you do tuck it in, try pinrolling your trousers a little at the ankle, it stops the outfit looking too formal up top and too loose down the bottom.
And Then There’s the Shoes
Shoes change the whole mood of this more than people realise, I think.
- White sneakers or canvas shoes for anything casual
- Loafers or suede shoes if you’re going smart casual
- Espadrilles for resort or beach type settings
- Simple sandals if you’re somewhere by the water
Keep it simple basically, bulky sneakers or anything too loud just pulls attention away from the shirt and the shirt’s supposed to be doing the talking here, not the shoes.
Linen, Cotton or Silk
Linen
Lightweight, breathable, wrinkles the second you sit down in it, which is honestly part of the charm if you ask me. Good for travel, beach trips, basically anywhere the heat’s doing most of the work.
Cotton
Bit more structured, holds its shape better, easier to just chuck in the wash without worrying about it too much. If you want one shirt that does both casual and slightly dressed up, cotton’s probably the safer bet.
Silk or Blends
Smoother finish, tends to show up more in designer stuff and evening wear. Not something you’d wear to the beach really, but nice when you want a bit more shine without going properly formal. If you’re building out your fabric knowledge a bit more generally, worth reading up on chambray shirts too, since chambray’s in a similar breathable, warm-weather category but behaves completely differently once you actually start styling it.
Fit Is Where Most People Go Wrong
This is where most men mess it up honestly and it’s not even really about the collar.
- Shoulders should sit right at the edge, not drooping past it
- The body should follow your shape without clinging or ballooning out
- Length should land around mid-zipper, not shorter, not longer
A slim fit looks good in photos but feels awful if you can’t actually move your arms properly. Comfort and proportion matter more than chasing a tight fit, I’ve learned that the hard way. If you’re between sizes, size up rather than down, this shirt’s meant to sit away from the body and going too small kills that completely. If you’ve never really sat down and worked out how a shirt’s meant to fit you specifically, I did a longer breakdown on getting your shirt fit right that’s worth a look before you buy your next one.
A Few Combinations I’d Genuinely Wear
If you want a simple Cuban collar shirt outfit that doesn’t need much thought, start here honestly. White one, beige chinos, white sneakers, about as easy as it gets and it works pretty much anywhere. If you’re someone who already leans on white shirts a lot, I went deeper into that specific styling territory in my piece on white shirt outfit ideas and a lot of the same logic carries over here anyway.
Linen version with light trousers feels breathable and just slightly polished, good for warm evenings I find. Printed shirts do best with plain shorts and neutral shoes, let the print do the work. A solid navy or white one with dark jeans is one of those combinations that just works for pretty much any casual dinner without overthinking it too much.
Cuban Collar Shirt for a Wedding
People assume this shirt’s too casual for a wedding, but honestly it depends entirely on the wedding itself. For a daytime or destination wedding, especially anything outdoors, a solid linen one in a muted colour with tailored trousers and loafers reads as intentional rather than underdressed. Save the loud prints for the pool party the next day, not the actual ceremony. If the dress code says formal though, this isn’t your shirt, that’s what a proper dress shirt’s for.
There’s also a bit of a middle ground worth knowing about, wearing it under a light-coloured suit jacket for a summer cocktail hour type thing. Softens the whole look compared to a dress shirt and tie, but still holds up fine under a jacket. That’s really the appeal of this shirt generally I think, it can go from a beach afternoon to dinner later that night without you having to change into something completely different.
Long Sleeve Versions
The short sleeve one gets all the attention, but the long sleeve cut, sometimes people call it the full sleeve Cuban collar shirt, is worth knowing about too, especially once the weather starts cooling down or you’re somewhere with the air conditioning working overtime. Keeps the same relaxed open collar but gives you a bit more coverage and it layers surprisingly well under a light jacket without looking like you’re forcing two different styles together.
Cuban Collar vs a Polo Shirt
Both casual, both collared and honestly people mix them up more than you’d think. Polo’s got that soft, folded collar and buttons partway down, built for more of a sporty, clean look. Cuban collar sits flatter, opens all the way, reads more relaxed-resort than sporty-casual if that makes sense. If you’re choosing between the two for something slightly dressier, like layering under a blazer, I actually wrote specifically about wearing a polo shirt with a blazer and that combination genuinely works better with a polo than it does with a Cuban collar, in my experience anyway.
Why It Works on Pretty Much Any Body
That boxy, loose cut is doing more work than people give it credit for, honestly. Skims the torso instead of clinging to it, which means you don’t really need a particular body type to pull this off. That said, a few small tweaks help depending on your build.
Short Guys
Shorter hems, lighter colours, maybe a vertical stripe if you want a bit of extra height in the look.
Tall Guys
You can get away with longer hems and bolder prints without it looking like too much, to be honest. Cropped trousers pair nicely too.
Muscular Build
Stretch cotton or a linen blend gives you a bit of room without pulling across the chest. I’d avoid anything marketed as slim fit unless you’ve actually tried it on first, trust me on that one.
Slim Build
Prints and texture add a bit of visual width, which helps if a plain solid shirt tends to look a little flat on you.
Plus Size
This is actually where the shirt does its best work if you ask me, since the boxy cut was never built to cling in the first place. Go for a slightly longer length so it doesn’t ride up when you sit down and stick to vertical patterns or solids over anything with a busy horizontal print.
On Colour
If you’ve ever struggled with certain colours washing you out or just not sitting right against your skin tone, that logic applies here too. I wrote more specifically about shirt colours that work best against darker skin tones and most of those same rules carry over pretty directly to how a Cuban collar shirt ends up looking on you. On the lighter, more playful end, a pink shirt paired the right way with your trousers is another one worth trying once you’re comfortable stepping outside plain white and navy and the same goes for grey paired with the right trouser shade if you want something a bit more neutral or even grey against white trousers for something cleaner and more minimal really.
If You Just Want to Not Think About It
Cuban collar shirt, chinos, white sneakers. Linen version, light trousers, loafers. Printed shirt, plain shorts, canvas shoes. Solid colour, dark jeans, sneakers. Just pick whichever matches your day and go, honestly it’s not that deep.
Is It Still Trending
Yeah, and it just keeps coming back every warm season really, without ever fully going away in between. Cuban collar shirt fashion moves in waves rather than disappearing for good, a few quiet years, then it’s back on runways and high street racks again. In neutral colours it looks classic enough that you could wear it for years without it feeling dated. In prints it feels a bit more of-the-moment I suppose. Either way works honestly, just depends what you’re going for.
Bits People Keep Asking Me
Can I wear a Cuban collar shirt to the office? Depends entirely on the office to be honest. In a relaxed, casual workplace, yeah, especially in a solid colour. Anywhere more formal, just stick to a regular dress shirt instead.
Is it formal or casual really? Casual to smart casual, never properly formal, not in my experience anyway. You can dress it up a bit with the right trousers and shoes but it’s never going to read as suit-and-tie appropriate.
What do I wear it with when it’s colder? A long sleeve version or just layer a short sleeve one under a light jacket. It’s mainly a warm-weather shirt at heart, but it doesn’t have to completely disappear once the temperature drops a bit.
Anyway, getting this shirt right isn’t really that complicated once you stop treating it like a formal shirt that just happens to have a different collar. Keep the fit clean, keep the rest of the outfit fairly simple and just let the collar actually do what it was designed to do in the first place.
Deepak Bhandari has spent 10 years in personal styling, helping men dress with more confidence and less guesswork. He’s the founder of Deepu Fashion, where he writes about style, grooming and everyday outfit ideas that actually work in real life. Follow him on Instagram for daily style tips and inspiration.
