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Winston Kong – Designer to the Stars

Winston Kong was a pivotal name in the Toronto fashion design scene for over 30 years. Couture evening and bridal wear were his specialty, and he crafted dresses for various Canadian and international socialites including Sherry Eaton, Mila Mulroney and, at one point, the Princess of Japan.

Kong was born in Ipswich, Jamaica, in 1934. He was raised by his Jamaican mother and father of Chinese descent. He later moved to the United States to continue his education and studied hotel management at Cornell University.

While working at a hotel, Winston had a fortuitous encounter with a famed editor of the International Herald Tribune who, after several conversations on style, film and fashion, gave him the advice to pursue a career in fashion.

Kong took this advice to heart and went on to study at the Fashion Institute of Technology.

Winston, ExcellenceMag, Donna Holgate
Ruched gold silk lame, strapless flamenco dress, skirted with black silk taffeta. Source: Excellence Magazine, 1987 Fashion Editor: Donna Holgate Model: Vivienne Brown Photographer: John Wild

Early Life and Career

According to an article written by Tony Wong in Caribbean Life, Kong moved to Canada in 1964 to “work for a year,” and was designing dresses for a Toronto boutique owned by David Smith. He decided to stay and by 1966, Kong opened his own couture boutique in Toronto, initially on Gerrard Street, then relocating in 1970 to Cumberland Street in Yorkville.

Kong’s boutique was known for its salon-like atmosphere that resembled the couture houses of Paris, where clients would come to discuss their problems, relationships and personal lives while having their dress made. For Kong, the business of design was much greater than the purchasing of merchandise, it was the connection created between him and his customers.

“He was really handsome and had such charisma and charm,” says Fernanda Raposo, his right-hand person for 17 years. “He would come up and say ‘Fernanda, I’ve just had this vision,’ and start sketching. ‘Let’s get this dress done, let’s bring it to life. I want this dress in the window by tonight.’ The boutique was always filled with fresh white gladiola flowers and music.”

Despite being a minority in a field that is known for a lack of diversity, Kong never felt as though his ethnicity kept him from achieving his goals.

“He had a joy for life that was addictive to people that surrounded him,” says Kong’s nephew, Jeffery Kong. “He had a great bunch of friends, some in the business and a lot outside of it, and he was well-loved by people that surrounded him.”

Kong’s passion for life sparked a variety of interests. He had a love of operatic music, painting and impressionism, all of which were reflected and translated into his designs.

“He looked at his work with curious eyes,” says Jeffery. “What he was breathing in, he was also demonstrating in his art form. It was genuine, it wasn’t something that was prefabricated, or copied. His work was a reflection of the type of life that he led,” adds Jeffery.

Breaking Barriers

Despite being a minority in a field that is known for a lack of diversity, Kong never felt as though his ethnicity kept him from achieving his goals.

“He was very confident in who he was and what his talent was. He knew he could deliver, so it was never ever about race,” says Jeffery.

Winston Kong was a pioneer in many aspects. He was the first of many relatives to delve into creative fields, including Jeffery, Kong’s niece, Jeanette Kong, who is a documentary filmmaker, architect Brigitte Shim, and Walter Chin, a well-known New York fashion photographer. Whether related or not, it was Kong’s nature to support young talent.

Kong was known for his entrance making, silk taffeta ball gowns. His style was heavily influenced by his Jamaican roots, when it came to the colour and shapes used in his designs.

According to Jonathan Walford, fashion historian and curatorial director of the Fashion History Museum, ‘He would never make more than four of any design, and even then, each dress was slightly different based on the client’s specifications.”

His style was heavily influenced by his Jamaican roots, when it came to colour and shapes used in his designs

Influence and Legacy

Kong’s designs were featured on many runways throughout his illustrious career, including the prestigious 1982 UNICEF benefit show, where he presented a stunning finale that prompted one French publication to note their surprise that such “opulence and creativity could exist on this side of the Atlantic.”

Kong wasn’t born into wealth, but found success through a combination of hard work and talent, which eventually led to him receiving the Order of Canada in 1987.

Jeffery, a designer himself who worked for many years in Europe and the U.SA., says that his uncle helped him find his footing in the formative years of his career, along with many other young Canadian artists hoping to break into the industry.

Winston Kong closed his boutique in 1995, marking the end of a historic career in the Toronto couture community. He passed away in 2005, but is still remembered for the lasting impact he left on the local and global fashion communities alike.

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NameWinston KongYearsb.1934 - d.2005BirthplaceIpswich, St. Elizabeth, JamaicaEthnic OriginJamaican, ChineseOccupationsFashion Designer, MentorShare

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