Jawara Alleyne SS25: Island Underground

Image: Ali Salkini (@ali.macalino)

There’s something unmistakably captivating about Jawara Alleyne's work. His latest collection, Island Underground, for Spring/Summer 2025, is a tactile journey that challenges and transcends gender norms, wrapping the body in layers of storytelling, Caymanian culture, and a uniquely Caribbean form of machismo. Effeminacy and masculinity intermingle, safety pins clutch dreamily manipulated fabrics, and every knot speaks to a new kind of rebellion.

Alleyne’s vision for this collection is a powerful tribute to his roots—his creative playground is the Cayman Islands, a Caribbean archipelago that thrives with the influence of over 130 nationalities. “I’ve always been inspired by a dare-to-be-different attitude, and I wanted this collection to reflect individuals who have inspired me to write my own story,” Alleyne explains. Island Underground is that story—a fusion of tradition and the progressive spirit pushing Caymanian culture into new territory.

Image: Ali Salkini (@ali.macalino)

Alleyne didn’t craft this collection in a vacuum. The influences are clear—he draws from Caribbean icons like Ann Marie ‘Hairstyle’ Tomlinson, dancehall legend Gerald ‘Bogle’ Levy, and pirate mythology through Captain Black Terrance of the Bloody Bay Buccaneers. Yet, it’s the Cayman Islands Government that has fully recognized the value of Alleyne’s global rise, backing the designer through the Ministry of Culture and Tourism, championing his work as a cultural ambassador for Caymanian talent on the world stage.

What makes Island Underground so striking isn’t just the political and cultural narrative; it’s also the raw beauty and tactility of the collection itself. Alleyne has a unique way of capturing the shimmer of Caribbean life. The hues in his work seem to bounce like sunlight on water. “I imagined the way you see colour reflected off water,” he notes, giving the garments an iridescent quality that feels alive, fluid, and deeply connected to his island home.

Image: Ali Salkini (@ali.macalino)

Cayman’s Minister of Culture, Dwayne Seymour, has praised Alleyne for seamlessly weaving heritage into fashion. “By embedding our history into each piece, Jawara celebrates our authenticity while pushing boundaries,” Seymour said. Alleyne’s work doesn’t just honour the past—it reimagines it for a new generation. His designs are less about nostalgia and more about evolution, where culture is a living, breathing entity, ready to be remixed and redefined.

And while Alleyne has garnered significant global attention, the heart of his SS25 collection returns home. On November 2nd, the Island Underground collection will be showcased at the National Gallery of the Cayman Islands—a homecoming that feels deeply personal for Alleyne. “Bringing my collections back to where it all began is more than just fashion—it’s about sharing my story with the world,” he says. The event marks a powerful moment for the Cayman Islands, with Alleyne’s work acting as a cultural declaration, presenting Cayman as not just a tropical getaway but a hotbed of artistic and creative talent.

Image: Ali Salkini (@ali.macalino)

The exhibition will also feature a collaboration with Caymanian artist Stefan Langlois, whose charcoal and graffiti works layer Alleyne’s designs with a visual language that amplifies national iconography and colour theory. This infusion of fine art adds another dimension to Alleyne’s work—an exploration of cultural identity that feels at once modern and deeply rooted in tradition.

But Alleyne doesn’t just play with femininity and cultural motifs—there’s also a strong undercurrent of machismo running through the SS25 collection, and it finds its boldest expression in a collaboration with Timberland. The brand’s iconic Original Yellow Boot has long been a staple of Caribbean fashion, filtered through hip-hop influences and streetwear culture. This partnership between Alleyne and Timberland underscores the unshakable connection between Caribbean youth culture and global fashion trends.

Image: Ali Salkini (@ali.macalino)

The Island Underground collection amplifies this machismo, but Alleyne’s take on masculinity is complex—never aggressive, always thoughtful. The ruggedness of Timberland’s boots contrasts with the delicate knot-work and draping fabrics, creating a visual tension that reflects the shifting definitions of power, gender, and cultural expression.

In many ways, Island Underground is Alleyne’s most mature collection yet. It’s not just about aesthetics—it’s about what fashion can mean, what stories it can tell. Alleyne’s work is imbued with a sense of purpose, an understanding that clothing can be a medium for both personal and cultural storytelling. As Kenneth Bryan, Cayman’s Minister of Tourism, put it: “Jawara’s ability to merge local influences with international appeal reinforces our commitment to showcasing Cayman as a hub of innovation and creativity.”

Image: Ali Salkini (@ali.macalino)

At the end of the day, Island Underground is a reminder that small nations like the Cayman Islands have a wealth of stories to share with the world. Jawara Alleyne’s SS25 collection is a testament to the power of culture, community, and creativity. And as Alleyne continues to carve out his place in the global fashion scene, it’s clear that his roots remain firmly planted in the Caribbean, where every stitch tells a story.