Shopping in Bermuda can feel daunting. High prices, limited variety, and the sameness that comes with living on a small island all shape the experience.
What can feel even more challenging is trying to find stylish clothing for cold climates when Bermuda’s weather is subtropical. Frost, snow and winter layering are far removed from everyday life here, particularly for men who care about style and want to arrive looking prepared rather than improvised.
Something warm and comfortable can take the edge off long waits in airport lounges and chilly plane cabins, but what you arrive in matters just as much. That old pair of jeans and a comfortable hoodie may feel easy in transit, but they will not always suit a big city restaurant, a business meeting, or a formal event waiting on the other side of the flight.
To understand how Bermudians blend comfort and style when travelling to colder climates, we spoke with two retailers who know this well.
TABS, founded in 2013, has become a go to for modern island style, while Shannon’s Boutique has spent more than forty years helping men dress for every kind of trip.
Classic and elegant
At TABS, the conversation focused on intention.
“Over the years at TABS, I’ve seen Bermudians become much more intentional about how they travel,” said Rebecca Singleton, founder and CEO.
Many of their customers are business travellers who often go straight from the plane into meetings or dinners. As a result, “comfort is essential, but they still need to look polished the moment they land.”
That expectation shaped the store’s approach. TABS introduced performance pieces designed for long flights and quick transitions. Their checked button up travel shirt “looks like a classic tailored shirt but is made from performance fabric that’s breathable, wrinkle resistant and easy to care for”. It lets travellers arrive ready without needing to change.
Travel style also reflects larger influences. Motown in the 1970s brought a sharp, soulful polish to African American style, while the Black Panthers added fitted, intentional dressing with crisp leather and structured lines. The Dandyism of the Congo travelled outward too, influencing Western menswear with colour and elegance. These movements blend ease with purpose, a balance many travellers still look for.
TABS echoed that balance when highlighting their performance shorts and quarter zips.
“We launched our long-awaited performance shorts in 2025, along with performance quarter zips for easy layering,” Ms Singleton said. These pieces move easily from transit to destination.
Warm and stylish
Layering becomes even more important as Bermudians enter colder climates.
“Layers are key,” Ms Singleton said. Their fleece lined performance quarter zip fits over a shirt or polo, keeps warmth in without bulk, and maintains a clean look. Its tailored cuff “makes slipping a jacket on effortless,” helping travellers adjust as temperatures shift.
Style remains central. “Our customers don’t mind standing out. They enjoy keeping the Bermuda look strong while adapting it confidently for their destination,” they said.
Although Bermuda has long embraced global fashion trends, that Bermudian identity has its own fashion lineage. The blazer and loafers reflect the island’s British influence, but the Bermuda shorts and knee-high socks are distinctly ours. Inspired by the pink sand, the ocean, the Bermuda flag and other bright combinations, we embraced bold colours for our shorts and socks. Traditional tones bring restraint, while pastel and vibrant shades signal ease and confidence. The blend of British tailoring and island colour still feels true to how we dress today.
This sense of identity shapes TABS’s specialism.
Ms Singleton said: “Our store specialises in the Bermuda suit.” Even though the shorts are not suited for winter travel, the mindset of mixing ease with polish guides how they help customers pack light and stay sharp.
“Don’t pack your blazer, wear it on the plane,” Ms Singleton advised. Hanging it once onboard prevents wrinkles and saves suitcase space. Colour matched shirts allow fewer bottoms but more outfits.
TABS covers the essentials for men who want to travel comfortably and still look sharp.
Move with the times
Shannon’s Boutique builds on that approach, widening it with pieces for winter trips, cruises, city breaks and formal events.
The conversation at Shannon’s reflected this broader range. With more than 40 years in business, the store has seen travel wear evolve.
“In general, travel wear has evolved from smart casual to comfort wear,” they said. “But we still have customers that like to dress up.”
Their customers often come with a particular trip in mind. This can mean winter city breaks, cruise wear, or tailored looks for events abroad.
Layering remains essential. Shannon’s recommends “clothing that can be layered such as zip down sweat tops, lightweight jackets like bubble jackets, tracksuits and scarves.” These pieces help travellers move through cold airports, long flights and shifting weather without carrying heavy coats.
Seasonality shapes what they offer. In warmer months, they carry cotton or linen blend shorts, drawstring trousers, short sleeve button downs, polo shirts and dressy casual T-shirts. As temperatures drop, sweaters, tracksuits, sweat suits, trending jeans and casual jackets help customers dress for their destination.
Shannon’s also specialises in suits for destination weddings and formal events. They guide customers toward mix and match pieces that travel well and still look polished. “Not really,” they said when asked about common mistakes, noting that most customers seek guidance before their trip.
Together, the two stores offer a wide range of options for men preparing for colder climates. TABS leans into performance and coordinated dressing. Shannon’s expands those options with variety, seasonality and pieces suited for the many different trips Bermudians take.
With the right layers, thoughtful fabrics and well-chosen pieces, winter travel does not have to feel overwhelming. A few smart choices can keep travellers coming from Bermuda warm, comfortable and stylish from take-off to arrival.
