When she was 13 years old and a pupil at Bishop Anstey High School, Janelle "Penny" Commissiong left Trinidad for New York with her family where she lived for about ten years before returning home in 1976. While in the United States, Commissiong studied at the Fashion Institute of Technology and was seeking to get into the advertising side of the then-fledgling couture business here.

In 1977, Commissiong participated in the Miss Trinidad and Tobago Pageant, easily winning the title and going on to represent the nation in the Miss Universe competition in Santo Domingo that same year. Trinbagonians were still on a high from Hasely Crawford's victory in the Men's 100 metres sprint at the Montreal Olympics the previous year.

Four days before the actual final, Commissiong won the Miss Photogenic fringe competition, becoming only the second black woman to have ever won that title. The Trini beauty would go on to become the first black woman ever to wear the Miss Universe crown. Of course being the first, Commissiong had to deal with some measure of racism in the earlier part of her reign, but she stood her ground and commanded respect.

Commissiong was, during and following her reign, a public advocate for black rights in nations where people of African ancestry were minorities, and she campaigned for world peace. She was awarded the Trinity Cross at the Independence celebrations of 1977. Three postage stamps were also issued in her honour and a BWIA DC9 was named after her.

In 1986, a pretty petite lady captured the hearts of Trinbagonians as she was introduced as one of the participants in the Miss Trinidad and Tobago leg of the Miss World competition. Born in Port of Spain, Giselle Laronde moved to San Fernando with her family as a child and attended the St Peter's School at Pointe-a-Pierre before moving on to St Francois Girls' College in Belmont.

Having pursued a secretarial course at the San Fernando Technical Institute, where upon graduation in 1985 she received awards for Best All Round Student and Most Helpful Individual, Laronde landed a job at the Trintoc Employees Credit Union (TECU) in Marabella as a secretary.

The following year she got the nod to represent Trinbago at the Miss World finals in London where on November 13 at the Royal Albert Hall, Laronde became the first woman and to date the only woman from here to be crowned Miss World.

Her rewards from the Government included the Chaconia Medal, having four commemorative stamps issued in her name and a BWIA plane named in her honour. Laronde went on to attend Goldsmith College, University of London, where she completed her degree in Sociology and Mass Communications. She is married to Heathcliff West and they have two children. She is presently the communications manager at Angostura.

Still hailed as one of the most beautiful women in the world, Wendy Fitzwilliam was in the midst of her law studies when she in 1998 decided to enter the Miss Trinidad and Tobago Universe competition. Having easily won the local competition, Fitzwilliam went on to compete in that year's Miss Universe pageant held at the Stan Sheriff Center in Honolulu, Hawaii.

Fitzwilliam's regal air and perfect evening gown presentation won her the favour of the judges and made her the favourite to capture the crown that night. However, once the final three were announced, her halting final answer to the question caused some anxiety. There was a deadlock between her and Veruska Ramirez of Venezuela, who had won the swimsuit competition with the highest score ever seen at the time and gave a straightforward answer to the question. Because there were eight members on the panel of judges and no way to break an eventual tie, the decision promised to be a nail-biter.

In the end, Fitzwilliam prevailed and became the first contestant in history to win wearing a bikini in the swimsuit competition, denying Ramírez that title as well. Her win came 21 years after Commissiong. Fitzwilliam was actually the third person of African heritage to win the Miss Universe title.

During her reign, Fitzwilliam was honoured by the United Nations and bestowed with the title of UNAIDS and UNFPA Goodwill Ambassador for her work in HIV/AIDS education and awareness. Fitzwilliam founded the Hibiscus Foundation, which provides assistance to children's homes, including the Cyril Ross Home that cares for children with HIV/AIDS.

Fitzwilliam passed the Bar in 2000 and was the international spokesperson for Clear Essence Skin Care. She made several notable television appearances hosting segments of Wild On for US-based E! Entertainment Television as well as the Miss Universe Special for the same network.