Jawara Alleynes makes the case for ‘Island Underground’ at LFW

Island Underground is effeminacy: body parts swathed by signature fabrics, accentuated by safety pins, manipulated into dreamy knot-work, punctuated by machismo.

Jawara Alleyne's signature transcends gender, and uniformity, yet makes space to live and thrive among these subsets. With culture and storytelling at its core, Jawara Alleyne defines Spring/Summer ’25 as 'Island Underground'.

'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 find my way of doing things… write my own story. Island Underground is [characterised by] individuals who take inspiration from our culture and fuse it with progressive expression, mixing in references that push the culture forward.'

Island Underground, derived from the musings of Ann Marie ‘Hairstyle’ Tomlinson, Gerald ‘Bogle’ Levy, and Captain Black Terrance of the Bloody Bay Buccaneers, is a masterclass in Caymanian artistic expression.

It depicts a fresh vision that draws from the experiences and shared cultural identities of the Cayman Islands people, living amongst 130 nationalities in the tiny three-island Caribbean archipelago.

The Cayman Islands Government, through the Ministry and Department of Tourism and the Ministry of Culture, is fully invested in this collaboration, recognizing the value of elevating Caymanian talent on a global stage.

The hues within the collection capture the essence of shimmer, 'I imagined the way you see colour reflected off water', Alleyne notes.

Minister of Culture, Honourable Dwayne Seymour, expressed his excitement about the cultural impact of Alleyne’s work: 'By weaving our heritage, art, and identity into each piece, Jawara celebrates the authenticity of our culture while pushing the boundaries of modern fashion. His work not only honours our past but reimagines it for future generations.'

Minister of Tourism, Honourable Kenneth Bryan, emphasized the significance of promoting Caymanian talent globally: 'Jawara Alleyne’s ability to merge local influences with international appeal is remarkable, and it reinforces our commitment to showcasing Cayman as not just a premier destination but as a hub of innovation and creativity. His global impact demonstrates how our island’s culture can resonate powerfully on the world stage.'

On November 2, Island Underground will be defined in an artistic showcase at the National Gallery of the Cayman Islands, marking a distinctive homecoming for Alleyne and his Cayman Islands-inspired collections.

Reflecting on this, Jawara Alleyne said, 'Bringing pieces of my collections and sharing the sources of my inspiration in the place where it all began, is deeply personal. It’s about more than just fashion — it's about honouring where I come from and sharing that story with the world. The National Gallery is a sacred space for me, a place where art and culture meet. This exhibition is a way to connect my work with the people and the community that answered and supported my calling, and it’s a powerful moment to show the world what a small nation in the Caribbean can inspire. Island Underground as an exhibition, is a cultural declaration.'

The visual arts element was deliberate and embedded in the contributions of Caymanian artists. National iconography and colour theories combined with charcoal and graffiti elevate this visual language, created by Stefan Langlois.

Alleyne’s fascination with art lends to the themes of the collection, curated by Natalie Urquhart, director of the National Gallery of the Cayman Islands.

Add Timberland to the mix and all elements of machismo are suddenly amplified. This partnership is symbiotic as the impact of the quintessential pair of ‘timbs’ – by way of Hip Hop influences – had always been a part of the Caribbean footwear narrative.

The Original Yellow Boot’s distinctive wheat colour, unparalleled craftsmanship, and enduring comfort have solidified its status as the most recognizable boot in the world; a testament to authenticity and the power youth culture has on brands.

Timberland is thrilled to partner with Jawara Alleyne for the SS25 show. The partnership builds on the recent announcement of their ICONIC campaign celebrating the legacy of The Original Yellow Boot and the resilience of icons.