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From One T-Shirt to Awleh!: Brian Watler Jr’s Cayman Design Story

While studying abroad, Brian Watler Jr. set out to find something simple, a shirt that could represent Cayman at an international festival. Surrounded by students proudly wearing pieces that reflected their countries, he realized Cayman had no equivalent that was readily accessible. That absence became the starting point of Awleh!

The Creative Process Behind Awleh! 

Brian’s first design was not the one people recognize today. He described it as unbalanced and, in his own words, “ugleh.”😂 Despite the favorable public response, he continued to refine it.

He reworked the Union Jack, adjusted the overall structure, and developed the design until it reached a point that felt right.

📝: Most ideas fail early because they are judged too quickly. Brian let the idea evolve until it could stand.

Brian Watler Jr. | Photography by ZEAL Cayman

Awleh! has since extended to a full suite of merch, products and collectibles. 

The t-shirt represents only one layer of Watler’s broader creative practice. Alongside building Awleh, he works across performing arts, media, photography, and design, with a role at the Cayman Islands National Museum that further connects his work to cultural storytelling and preservation.

Watler said his vision for Awleh extended beyond clothing from the outset. “Initially the idea that I had was for Awleh to become a culture center… somewhere you can go, do workshops, cooking, thatching… and experience what it is to be Caymanian”.

Naming the Brand, Carrying the Past

“Awleh” is rooted in a word Brian’s great grandmother used often, a variation tied to “Almighty,” woven into everyday Caymanian expression. His great grandmother was known for her connection to the land, especially her garden. Even in her later years, she remained committed to it, moving with purpose, tending to what she had planted.

Awleh! follows the same pattern. Something planted simply, nurtured over time, shaped through care and consistency.

Key Takeaways 

Brian’s journey is defined by a pattern of decisions:

  • Identify what is missing
  • Build the simplest version of it
  • Revisit the work until it improves
  • Trust your process, even if it differs from others
  • Release before it feels complete
  • Let the response and your standards guide the next step

"You have ideas, revisit them… just let them evolve and go at it. For me, it was just a t-shirt… but it grew to become the Cayman Islands flag t-shirt. If you have an idea to promote and celebrate Cayman, go for it, no matter how simple it is.”

- Brian Watler Jr.
Create Without Knowing the Outcome

That is the nature of creative work. You rarely know what something will become when you start. The value is not in predicting the outcome, but in committing to the process.

Check out Awleh! below. Patriotic Cayman gear that stands out. Wear your Caymanian pride.™

 

[Photos courtesy of Awleh]

Caymanian Creativity

Featuring: Brian Watler Jr. | Creator of Awleh!

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