Ask most Bermudians what Cup Match means and you’ll hear plenty about Somerset, St. George’s, cricket, camping, cassava pie, and who will be lifting the cup this year.
But for Bermudian entrepreneur and fashion designer Kennette J. Burgess, Cup Match tells a much deeper story—one of freedom, identity, resilience, and community.
Through her newest Distinct Apparel 2026 Cup Match Collection, Burgess hopes to encourage conversations that go beyond team colours and remind both residents and visitors why Bermuda celebrates this national holiday in the first place.
“Fashion has always been a way people tell their story,” Burgess said.
“Behind every Cup Match shirt is an opportunity to celebrate not only our favourite team, but also our history. Cup Match exists because of Emancipation. It reminds us of Mary Prince, of freedom, of the strength of our ancestors, and of how far Bermuda has come.”
Rather than creating clothing that simply celebrates cricket, Distinct Apparel’s newest collection intentionally weaves Bermudian heritage throughout its designs.
One of the featured collections incorporates African-inspired patterns alongside words including Emancipation, Freedom, Mary Prince, Bermuda, and Cup Match, encouraging people to proudly wear clothing that sparks conversations about Bermuda’s history.
“We wanted people to ask questions,” Burgess explained.
“Maybe a young person asks why Mary Prince’s name is on a shirt. Maybe a visitor asks why we celebrate Cup Match. Those conversations matter. This is why we also wanted to partner with comedian Nadanja and Tellevision in our first ever CupMatch educational sitcom series to educate the public in a funny way on the importance of CupMatch. ”
You can watch Part 1 here on Instagram with Parts 2 &3 dropping this weekend https://www.instagram.com/p/DbGQZxcDrgs/
While history remains at the heart of the collection, Burgess also wanted the designs to reflect what Cup Match has become today—a celebration of family, community, friendly rivalry, and Bermudian pride.
This year’s collection includes apparel celebrating Somerset supporters, St. George’s supporters, neutral “both teams” supporters, and even a playful “Cupmatch-ish” design for those who admit they’re mostly there for the food, family, and fun.
“Cup Match has room for everyone,” she laughed.
“Whether you’re Team Somerset, Team St. George’s, both teams, or just there because your auntie’s fish cakes are legendary, there’s something beautiful about the way Bermuda comes together.”
Beyond fashion, Burgess says community impact has become equally important.
Throughout this year’s Cup Match season, Distinct Apparel is partnering with several community organizations and cultural events, using fashion to bring people together while supporting local causes.
The collection recently took centre stage during the Somerset Pre-Cup Match Explosion at Willowbank Resort, where local designers, musicians, vendors, and entertainers celebrated Bermuda’s creativity ahead of the holiday around an estimated 3oo to 400 people.
Distinct Apparel is also supporting the Proud To Be Us Fashion Show this Saturday at Cedarbridge, benefiting Special Olympics Bermuda and helping athletes raise funds to represent Bermuda internationally.
For Burgess, those partnerships are just as important as selling clothing.
“Business should never just be about business,” she said.
“It’s about creating opportunities, celebrating people, supporting charities, investing back into the community, and preserving our culture for future generations.”
That philosophy has become part of the Distinct Apparel brand.
Whether through school partnerships, community fundraisers, cultural celebrations, retail collaborations, or charity fashion shows, Burgess believes fashion has the power to educate, inspire, and connect people.
As Bermuda prepares for another Cup Match season, she hopes residents and visitors alike will pause to remember why the holiday exists.
“We celebrate our teams because of our history,” she said.
“We celebrate our freedom because of those who came before us. If our clothing helps someone remember that—or learn it for the very first time—then we’ve accomplished something much bigger than selling a shirt.”
The Distinct Apparel 2026 Cup Match Collection is available online at www.mydistinctapparel.com and through select retail partners across Bermuda, including Brown & Co., Caesar’s Pharmacy, Surprise, Bargain Hunters, and Casual Footware.
About Distinct Apparel
Distinct Apparel is a Bermudian lifestyle and fashion brand founded by award-winning entrepreneur and designer Kennette J. Burgess, MBA. The brand creates apparel inspired by Bermudian culture, empowerment, faith, tourism, and community, with collections celebrating identity, inclusion, and confidence for all ages and sizes.
