The OB Classics: Timeless Style, Year After Year

Some styles just stick. You know the ones. You wear them to death, take them on every trip, and somehow they always feel right. At Orlebar Brown, that’s exactly what we aim for. Pieces that go the distance, collections that actually get better over time, and silhouettes that don’t follow trends - they just become your go-to.

From our earliest Bulldog shorts to the silk resort shirts and tailored trousers you now see on every flight to Ibiza, our classics weren’t designed to make a big fuss. They were designed to be worn, packed, washed, re-worn and loved. Season after season.

So let’s take a look back. Here’s a round-up of some of the standout collections and pieces from over the years, and why they still earn a place in your wardrobe today.

It All Started with the Bulldog

We couldn’t do this without starting here. The Bulldog is where OB began. A pair of tailored swim shorts that weren’t trying to be board shorts, or baggy or brash. Just neat, clean, and ready for anything from a swim to a spritz at lunch.

What made the Bulldog so different wasn’t just the fit (though that helped). It was the mindset. These were swim shorts designed like trousers. Zip fly, side adjusters, darts for shape, and a proper waistband. Suddenly, you could go from beach to bar without changing. And just like that, resortwear started to feel grown-up.

Over the years, we’ve played with fabrics and patterns- from vintage Bond posters to scenic photographic styles, and more recently, jacquard textures and recycled performance materials. But the silhouette? That’s stayed the same. Clean, mid-length, flattering. It just works.

The Giles Shirt: Not Just a Holiday Shirt

The Giles Shirt first landed in the collection as the perfect partner to your Bulldog shorts. Lightweight, slightly structured, and sharp enough to wear in the city once you were back from Mykonos.

What makes the Giles stand out is its simplicity. It’s tailored, but not stiff. You can wear it open with the sleeves rolled, or buttoned-up for dinner. And it comes in everything from breezy linen to brushed Italian cotton to subtly striped seersucker.

We’ve seen it in plain white (still a best-seller), all the way through to styles with embroidery, piped bib fronts, and exclusive prints. But the shape? Still classic. Still flattering. Still OB.

The OB-T: The Tee That Feels Smarter

You’ve probably got at least one OB-T in your wardrobe. Maybe more. It’s one of those deceptively simple pieces that’s been part of the collection for years - and for good reason.

The OB-T was our way of doing a T-shirt with a little more thought. A curved hem so it sits better with shorts. A tailored cut that skims the body without clinging. Side-seam reinforcements and a subtle branded tab. Nothing over the top, just smart details that make it feel finished.

It’s also one of the most versatile things we’ve made. You’ll find it in soft cotton, linen blends, and even towelling for beach days. It layers under everything and holds its shape. The sort of piece you buy once, wear endlessly, and then come back for more colours next summer.

Classic Towelling: Still Going Strong

Towelling and OB go hand in hand. We’ve had it in the collection for over a decade now, and while trends have come and gone, it’s never left.

What makes towelling such a winner is how easy it is. Throw on a Sebastian Towelling Polo after a swim and you’re instantly in that off-duty, Riviera frame of mind. Or pull on a pair of drawcord towelling shorts and feel like you’re living in a Slim Aarons photo.

We’ve played with towelling in every direction - from full zip-up hoodies to robes and even the now-legendary Goldfinger Onesie, which is a nod to Sean Connery’s poolside style in the Bond film of the same name.

It’s playful, but still polished. That sweet spot OB always aims for.

The Summer Editions: A Look Back at Key Collections

Each year, we build out summer around a theme or inspiration. Sometimes it’s a destination. Sometimes an era. Always something that brings a little story to the season.

Here are a few collections that stand out:

Summer 2020: Riviera Redux

Inspired by vintage French coastal style, this one was all about clean tailoring, soft pastels, and nautical undertones. Think linen suits worn with open collars, pale pink long-sleeve polos, and stripe swim shorts. The colour palette was soft but smart, and the silhouettes felt like a throwback to the golden age of Mediterranean summers.

The Mallon Shirt made its debut here - a relaxed resort shirt with a revere collar and breezy structure. Perfect with white Bulldog shorts or drawcord styles.

High Summer 2022: Modern Jet Set

This collection brought in a bit more texture. Towelling polos, waffle knits, and slubbed cottons gave everything a tactile edge. Colours were a little deeper too - Night Iris, Rust, and Damson played alongside crisp whites and soft sands.

The Roddy Polo became a standout. A soft, lightweight knit that worked just as well for dinner as it did for daytime. It’s one of those pieces that quietly turns into a classic.

Resort 2023: Into the Tropics

This one was bold. Floral prints, silk shirts, and vibrant tones across our tailored shapes. It was a celebration of getaway energy after a few slow years, and it leaned into colour, contrast and fun.

The Maitan Silk Shirt really took off here. Printed with painterly florals and cut from Italian silk, it gave a smarter edge to summer shirting. Worn open with a Bulldog short, it’s still a firm favourite for those who want to make an entrance without going too loud.

The OB Classics You Still See Every Season

Some pieces never leave. They might get a new colour or fabric each year, but their place in the collection stays the same.

Here are a few names to know (and probably already own):

  • Bulldog Shorts: The blueprint. The benchmark. Always in the mix.

  • Setter Shorts: A shorter cut, slightly more athletic, but still sharp. Great for taller guys who want balance.

  • Giles Shirt: Always there. Always relevant. In linen, seersucker, or cotton.

  • Sebastian Polo: The tailored polo that sits between smart and casual. Sometimes in linen, sometimes in towelling, always reliable.

  • OB-T: The base layer you build everything around. The classic white one still sells out fast.

  • Felix Polo: More relaxed than the Sebastian, with a soft placket and wider collar. Perfect for resort dressing.

  • Griffon Trouser: One of our lesser-known heroes. Tailored and slim, ideal with knitwear or shirts when shorts aren’t on the cards.

These are the pieces that form the backbone of our wardrobe, and probably yours too. They’re not trend pieces. They’re the ones that just feel right, year after year.

Why the Classics Work

There’s no trick to it. The classics work because they’ve been designed with a bit of restraint. Nothing added for the sake of it. Just good fits, quality fabrics, and attention to detail.

We always say: if it feels right, it is right. That’s the test for every OB piece, especially the ones we bring back season after season. And the ones that stick? They’re usually the ones that make getting dressed easier. No fuss, just style that fits your life (and your suitcase).

What’s Next for the Classics?

We're always looking at how to keep things fresh without reinventing what already works. You’ll see classic shapes like the Bulldog or the Giles continue, but with tweaks that make sense for now - new sustainable fabrics, technical linings, tonal hardware. It’s about staying true to the original, but giving it room to evolve.

Some pieces will get reissued in heritage colourways or with updated fits. Others, like our tailored linen trousers or open-weave polos, might start to form a new generation of classics altogether.

But the goal is always the same: to give you things you’ll wear for years. Not just for a season.

The OB Way: Timeless, Tailored, and Travel-Ready

We’ve never chased fashion. It’s not really our thing. What we care about is making clothes that feel great, look sharp, and fit your lifestyle. And the classics are where that comes to life.

Whether you’re packing for a quick weekend or a longer escape, the OB classics are the pieces you grab without thinking. They’re the ones you reach for when you want to feel good without overdoing it.

So if you’re building out your warm-weather wardrobe, start here. With a few great swim shorts, a sharp shirt, and a tee that fits just right. The rest will follow.