July 2, 2026 — Tobago’s well-known financial literacy advocate and educator Alana Alleyne, widely recognized across Trinidad and Tobago for empowering citizens to build sustainable generational wealth, is celebrating a proud family milestone on the international stage.
Following their migration to Canada, the Alleyne-Cupid family has been investing heavily in nurturing talent, confidence, and character. That dedication bore fruit as Alleyne’s 14-year-old daughter, Aalaiyah-Skye Cupid, made her major international runway debut on one of North America’s premier youth fashion platforms in Toronto. From Island Roots to International Runways
The teenage model’s transition from the shores of Tobago to high-fashion showcases in Canada underscores the expanding reach and versatility of Caribbean youth in the global creative arts:
Stepping Into the Spotlight: Walking for notable designers on a prominent North American youth runway, Aalaiyah-Skye showcased poise, technique, and stage presence, capturing the attention of fashion scouts and industry creatives alike.
Investing in Character & Discipline: Reflecting on the journey, Alana Alleyne noted that while financial literacy teaches people how to grow tangible assets, supporting children in creative disciplines builds essential intangible assets—resilience, self-discipline, and strong character.
Inspiring Caribbean Youth: Aalaiyah-Skye’s success serves as an inspiration for young aspiring creatives throughout Tobago, proving that local talent can seamlessly compete and excel on major international platforms when backed by strong mentorship and community support.
Reporter Jewel Greene-George has the full story on this proud cross-border achievement.
