Jeweline Roberts-Riley has unmatched history of pageantry and success

For five decades, Jeweline Roberts-Riley has been a key architect behind the pageantry of Montserrat Festival. Most of all she has groomed winners.

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"I love when an idea pops into my head and then I turn that idea into something tangible and spectacular," says Jeweline Roberts-Riley, shown circa 1980s.

From an early age, it was apparent that Jeweline Roberts-Riley was destined for a career in design. At 8, she was already sketching ideas for outfits. Her mom was a seamstress. While Mae Belle Roberts stitched dresses and other garments on her sewing machine, little Jeweline watched closely. She would also secure the scraps of fabric that fell to the floor and use them to design dresses for her doll. One day while her mom was sewing a dress, a piece of fabric fell. Jeweline assumed it was another unwanted swath of cloth that was probably headed for the rubbish bin. So she grabbed a pair of scissors, sliced the fabric, and created another outfit for her doll. It turns out that the cloth she cut was actually a sleeve and a collar for a dress her mom was making for a customer. “My mom was very upset. She said to me, ‘What am I going to do now? Don’t do that again. From now on ask me first before you cut anything.’ ”

Despite the mild scolding, her mother encouraged Jeweline’s love of design, fashion and creativity. It was the catalyst for a sterling career of creation that has been a labor of love.

Montserrat Festival has been an official event since 1962. It has produced award-winning calypsonians, a soca legend, regional queens and memorable masqueraders and revelers. Jeweline Roberts-Riley, working mostly behind the scenes and without much fanfare, has arguably had the biggest influence in the history of Montserrat’s Festival. Her roles have included pageant promoter, chaperone, costume designer, dance-group coordinator, dancer, dressmaker, troupe leader, fundraiser and consultant.

Jeweline Roberts-Riley plays mas with her troupe in the Montserrat Festival parade Jan. 1, 2019.

In the 1960s while at the Montserrat Secondary School, Jeweline, who hails from Kinsale Village, was a member of the Carnival Joy Promoters. Her early colleagues included Rose Willock, Joyce Gomez, Marjorie Riley, Jim Taylor, Norma Dyer and Vercil Edwards. On Boxing Day in 1963, the Joy Promoters unveiled a Hawaiian theme for Festival Day. They sported Hula-inspired skirts, Aloha tops, Hawaiian leis and ukuleles. They procured pieces of rope, loosened them, dyed them black and created wigs. Half a century later, Jeweline says that presentation remains vivid because of its creativity and effect. A few years later, while still a teen herself, Jeweline organized the first teen pageant in Montserrat. She recruited fellow students to participate, including Sonia Meade and Carolie Perkins, who would go on to win Miss Montserrat in 1972. The teen pageant became a vital platform that groomed contestants for the main Festival queen show.

In 1976, Jeweline chaperoned a Festival Queen contestant for the first time and designed her evening gown. Her client was fellow Kinsale native Catherine Ryan, who went on to win the crown. The following year, Jeweline co-chaperoned Patricia “Baby Sister” Bryan of George Street and designed her dress. Bryan also captured the Miss Montserrat title. Although she had not had any formal training in dressmaking at that time, Jeweline was now on a roll. Three more victories quickly followed: Rose Silcott (1978), Glendena Taylor (1979) and Diane Daniels (1980). Jeweline was in high demand. So she had to adopt a system of fairness.

“I always did it on a first-come, first-serve basis,” she says. “I didn’t play favorites. If a second girl came to me and wanted me to make a dress, I would always ask the first girl if she’s OK with it.” Asked her secret to success in dressmaking, Jeweline said: “I try to give the girls something that enhances their attributes. I always tell people that the dress doesn’t make you win. It’s you. Someone could go on stage with a bag on and still win.”

Jeweline Roberts-Riley is interviewed by Radio Montserrat in 2016 about her Order of Distinction award.

Despite her heavy involvement in Festival and other activities, Jeweline still had a regular job. After leaving school, she worked at the post office in Plymouth, and later at the Philatelic Bureau.

In 1985 she moved to New York and attended the Fashion Institute of Technology of the State University of New York, graduating with honors in 1991. She has come a long way from the days when she cobbled scraps of fabric to make dresses for her doll, but her love of design remains strong. She continues to return to Montserrat and promote her festival troupe. Over the years, the original Carnival Joy Promoters evolved to become the Titans Mas Movement, then Bijou Productions.

“I used to dream about [an idea] for a troupe,” she says. “Then I would wake up and start to sketch. I love when an idea pops into my head and then I turn that idea into something tangible and spectacular. I love the whole process.”

Though she has never been motivated by accolades, Jeweline was humbled when she was awarded an Order of Distinction medal at the 2016 Montserrat National Awards for her contribution to Festival. She was honored alongside other luminaries such as D.R.V. Frank Edwards, Austin Bramble and Cedric Osborne. It was an honor to be recognized by her country. And needless to say, she wears the title very well, thank you. “I feel very lucky,” Jeweline says. “Because I was given an award for something I really love doing.”

Somewhere, her mom is smiling.


Jeweline Roberts-Riley designed evening gowns for 15 queen show winners in Montserrat:

Catherine Ryan (1976)Mary Ann Gerald (1982)Jasmine Jno-Baptiste (2004)
Patricia Bryan (1977)Daphne Christopher (1983)Janelle Weekes (2005)
Rose Silcott (1978)Estelle Furlonge (2000)Techar Cuffy (2006)
Glendena Taylor (1979)Maudella Daley (2002)Naseeka Carty (2007)
Diane Daniels (1980)Francelise White (2003)Sharissa Ryan (2014)

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