The Evolution of the Polo Shirt: From Sports Fields to Style Icons
Some wardrobe staples sneak up on you. One day you’re throwing one on without thinking, and the next you realise it’s been the quiet MVP of your style for years. That’s the polo shirt.
From tennis courts to terrace bars, the polo has managed to land just about everywhere. It bridges that tricky gap between formal and casual, works with everything from chinos to swim shorts, and always looks like you’ve made a bit of effort (even when you haven’t).
This is the story of how it got there - and how Orlebar Brown made it part of the holiday uniform.
Where It All Started
Before the polo shirt was adopted by laid-back stylists and resort regulars, it was built for sport. And not just any sport - the kind that required a certain level of elegance even while mid-match.
Back in the 1920s, French tennis legend René Lacoste was fed up with the stiffness of traditional long-sleeved shirts worn on the court. He wanted something lighter, more breathable and easier to move in. So, he created a short-sleeved cotton shirt with a soft collar, button placket and ribbed hems. A simple fix, really. But it stuck.
The look caught on beyond tennis, too. Polo players in Britain took a liking to it (hence the name), and by the 1950s, it was being worn off the field as a more casual take on smart dressing. Hollywood got involved, naturally, with icons like Steve McQueen and Paul Newman making the polo shirt look impossibly cool. And once that happened, there was no going back.
From Uniform to Icon
By the time we reached the 1980s, the polo shirt had turned into a kind of shorthand for effortless style. It could be preppy or sporty, rebellious or refined. It was equally at home on a yacht or at a garden party. And it didn’t need much help to stand out.
The shape stayed pretty consistent. Short sleeves, soft collar, buttoned neck. But brands started playing with colours, fabrics, logos, and fits. It became a canvas for personal style. You could wear one tucked in with trousers or loose over swim shorts, layered under a jacket or solo with sunglasses and confidence.
The polo never really chased trends. It just kept adapting quietly in the background. And that’s what gave it staying power.
What Makes a Polo Shirt Great
There’s a lot of average polos out there. And once you’ve worn a good one, you’ll know exactly what separates the two.
It comes down to the fabric, the fit, and the finish.
A great polo feels good on. It’s soft, breathable and moves with you. The collar should sit right (no curling or floppiness), and the placket shouldn’t pull or pucker. The sleeves need to hit at the right point on the arm - not too short, not too baggy. And the hem should give you the option to wear it tucked or untucked without looking messy. Long sleeve polos are a great new addition to the classic design.
Sounds simple, but getting all of that right? It takes time. Which brings us to the OB way of doing polos.
The Orlebar Brown Take on the Polo
We didn’t set out to reinvent the polo shirt. We just wanted to make one that felt right for the way we travel and dress. Something that worked with a tailored swim short or a linen trouser. Something you could wear to breakfast, the beach, and then straight into cocktails on the terrace.
Our first polos followed the same philosophy we used for swim shorts - start with good tailoring and build around that.
You’ll see it in our classics like the Sebastian Polo. It’s cut with a slimmer silhouette, finished with branded buttons, and made in premium cotton or linen blends that keep their shape. It’s the smart one. Great with Alex shorts, good with Griffon trousers, and ideal for when you want to feel a little more put together.
Then there’s the Felix Polo, a more relaxed option with a shorter placket and slightly looser fit. It’s got a resort feel, great with a towelling short or layered under a lightweight overshirt.
We’ve also played with textured versions (like the Roddy or Burnham), which introduce open-stitch knits and fine stripes that nod to mid-century Riviera style. These are the polos that feel a little more elevated without losing the laid-back vibe.
Why They Work So Well on Holiday
It’s all about versatility. When you’re living out of a suitcase or getting dressed in a hot hotel room with limited choices, a good polo shirt is a blessing.
You don’t need to iron it to within an inch of its life. It’ll pair with almost any bottom half you packed. It’s smart enough to get you into most restaurants but still relaxed enough to wear for a coffee by the pool.
And with the OB range, you can cover every version of your holiday personality. The sharp, structured you. The linen-loving you. The slightly-sunburnt but still stylish you.
The Colours, the Fits, the Details
We keep the branding subtle. You won’t see oversized logos or contrast tipping unless it really suits the fabric. Instead, we focus on tonal buttons, soft garment dyes, and stitch work that holds up after a few washes in that hotel sink.
Colours range from clean whites and soft greys to warm seasonal tones like Caddie Green, Agave, and Damson. They all work with our signature neutral shorts and trousers, so mixing and matching is a breeze.
And if you’re feeling brave? A bold stripe or textured weave can make a big difference with very little effort.
From Day to Night (And Back Again)
The real reason polos have become icons is because they don’t need to change to suit the moment. You do.
A linen Sebastian Polo with a tailored short for breakfast? Easy. Swap the shorts for drawstring trousers and roll the sleeves, and you’re dinner-ready. Throw on a blazer or light knit and suddenly you’re hosting.
The same polo can do it all. That’s what style staples are about.
Why the Polo Still Matters
It’s not just another short-sleeved shirt. It’s a mood. The polo shirt has seen it all and still manages to be relevant.
It works because it doesn’t try too hard. It gives you structure without stiffness. It feels like the right choice for when you want to feel dressed without being “dressed up.”
At Orlebar Brown, we treat the polo like a building block. It’s something to rely on, experiment with, and return to. Not trend-led, just quietly confident. Which, if we’re honest, is the whole point.
FAQs: Polo Shirt Edition
1. What’s the difference between the Sebastian and the Felix polos?
The Sebastian is more tailored, with a structured collar and a smart silhouette. It’s ideal for dressing up a bit. The Felix is softer and more relaxed, with a resort-style placket. Great for low-key days and warmer climates.
2. Can I wear OB polos with swim shorts?
Definitely. That’s kind of the idea. A smart polo with Bulldog or Setter shorts is the classic OB pool-to-bar combination. Just add sandals or espadrilles and you’re sorted.
3. Do the polos come in linen or towelling?
Yes. We have polos in cotton piqué, linen jersey, silk blends and towelling. Each fabric gives the shirt a different feel, so you can choose depending on where you're going or how you like to dress.
4. What’s the best polo for evening wear?
Go for something more sophisticated - one of our Italian knitted polos such as the Horton or Bruno (dark colours and a little texture is right for the night). Pair it with trousers and loafers or clean trainers. It’s sharp without feeling overdressed.
5. How do I care for my OB polo shirt?
Wash on a cool setting and avoid tumble drying where possible. Linen and knit polos benefit from being laid flat to dry. A quick steam or low iron will keep everything looking fresh.
6. Are OB polos true to size?
Yes, though the fit varies slightly by style. Sebastian is slimmer, Felix is looser. We always recommend checking the fit notes online, but once you’ve found your size, you’re good to go across the board.
