The Best Orlebar Brown Styles for Your Winter Sun Getaway
When the days shorten and the sky turns pewter, the urge to escape to somewhere sun-drenched becomes irresistible. Whether it’s the golden beaches of Barbados, the crystalline coves of the Canary Islands, or the soft blush sunsets of the Riviera, a winter-sun holiday is the ultimate antidote to grey skies.
And as every Orlebar Brown man knows, style doesn’t take a holiday. The right wardrobe transforms a simple getaway into an experience. One that moves effortlessly from the poolside to the terrace, from a morning swim to an evening martini under the stars.
At Orlebar Brown, we design for these moments. Our collections are made for those who seek winter warmth in sophisticated style. Here’s your guide to four hero pieces that embody the spirit of travel, light, and laid-back luxury.
1. The Bulldog – The Tailored Icon of Every Escape
The Bulldog is where it all began. Orlebar Brown’s original tailored swim short and still the benchmark for all resortwear to follow. More than swimwear, it’s the perfect hybrid: sharp enough for lunch on the terrace, yet functional for a spontaneous dip in the sea.
Each pair is constructed from 60 precision-cut components, echoing the structure of a Savile Row trouser. Adjustable nickel-effect side fasteners, quick-dry recycled nylon, and a mid-length cut combine to create a flattering, timeless silhouette.
Opt for the Bulldog in Storm Grey or Amazon Green for a classic look that pairs beautifully with linen shirts and espadrilles. Or, if you prefer something with an edge, the Bulldog Solstice Bronze introduces subtle vibrancy, evoking the glow of sunset light.
Style it with: the Sebastian Linen Polo Shirt in White Sand or the Giles Linen Shirt for an understated Riviera aesthetic.
2. The Setter – Short, Sleek, and Designed for Freedom
For those who like a sportier cut, the Setter is the go-to choice. Slightly shorter than the Bulldog, it’s dynamic and flattering, capturing the confidence and ease of Mediterranean style. The Setter combines a streamlined shape with the same impeccable tailoring that defines all OB swim
shorts.
The Setter Riptide in Roller Blue captures the mood of a coastal escape — vivid yet refined. Pair it with a crisp white polo for daytime or a light linen shirt for sundown drinks. Its shorter length makes it perfect for those who value both freedom of movement and timeless style.
Every pair features adjustable side fasteners, a nickel-effect concealed snap closure, and a quick-dry Italian-woven fabric, ensuring that when you step from sea to bar, you do so with composure and confidence.
Style it with: the Terry Towelling Polo in Night Iris. Soft, retro, and effortlessly cool.
3. The Bulldog Photographic – Wearable Art for the Modern Voyager
If the Bulldog is the blueprint, the Photographic Bulldog is its artistic expression. Every pair in the range tells a story, an evocative snapshot of holidays past and present. From Slim Aarons’ Capri swimmers to vintage Monaco race cars, these prints capture the essence of wanderlust and
nostalgia.
Crafted in our signature Bulldog fit, the photographic shorts combine bold imagery with subtle sophistication. They are conversation pieces, perfect for those who prefer their resortwear with a touch of individuality.
This season’s standout design is the Bulldog Start Your Engines, depicting the Grand Prix de Monaco of 1956. A scene brimming with vintage glamour. The Deep Sea print, meanwhile, immerses you in tranquil blue tones reminiscent of midday Mediterranean light.
These shorts are best worn with simplicity. A plain white OB-T,perhaps, or an open Sebastian Polo. Let the imagery speak for itself.
Style it with: the Giles Linen Shirt in Matchstick or OB-T Classic Tee in Cloud.
4. The Down-Filled Merino Gilet – Layered Luxury for Cool Evenings
Even in paradise, evenings can bring a gentle chill. The Down-Filled Merino Knitted Panel Gilet bridges the gap between sun-soaked days and cooler nights. It’s the perfect companion for post-beach dinners, morning strolls, or those quiet hours before sunrise when the air is fresh and the sea
glows silver.
The gilet combines feather-light warmth with Italian-made Merino panels for texture and breathability. The fit is sleek, not bulky - designed to layer neatly over a polo or long-sleeved tee without disturbing your silhouette.
The Night Iris colourway offers understated elegance, while subtle tonal stitching adds depth. It’s an essential for any winter-sun getaway where evenings are best spent outdoors, Negroni in hand, as the temperature dips just enough to need a little luxury around your shoulders.
Style it with: the Sebastian Merino Polo or the OB-T Long Sleeve Merino in Biscuit for a refined layered look.
What to Pack for Effortless Resort Style
The art of packing for a winter-sun getaway is mastering refined minimalism. Choose pieces that do double duty. Shorts that can be worn to swim and to supper, polos that work for both beach bars and breakfast terraces.
Here’s an Orlebar Brown edit for the man who values style without excess:
- 2 pairs of tailored swim shorts (Bulldog + Setter)
- 1 pair of Photographic Bulldogs for statement days
- 2 shirts (Giles Linen + Ridley Open Collar)
- 1 Terry Towelling Polo
- 1 Down-Filled Merino Gilet for layering
- 1 pair of OB slides and 1 pair of loafers
- Lightweight sunglasses and a woven hat for sun protection
With this capsule, you’re prepared for every moment - from sunrise swims to starlit dinners.
Living the Orlebar Brown Way
Orlebar Brown was founded on a simple idea: to make shorts you can swim in. But the philosophy has grown far beyond that. Each OB piece is designed for how you live on holiday. Confident, curated, ready for anything.
A winter-sun break is not merely an escape; it’s a reset. And whether you’re diving into turquoise water or savouring coffee by the shore, the clothes you wear should enhance the experience. With Orlebar Brown, style isn’t seasonal. It’s a state of mind. One that travels with you wherever the sun leads.
