The Loopy Side of Fashion

The misadventure of a former retail business owner

“I remember leaving work and sitting downtown right at the corner of Yonge and Dundas by The Eaton Centre, says John I would sit there and observe the different fusions of style.”

Having a successful fashion business is not the easiest goal to accomplish in Toronto, especially with so many designers emerging every year.   John Jack had his share of ups and downs this crazy world we call the fashion industry. We were enjoying an evening of good conversation, music and food with his wife Lisa; former retail business owner John Jack reminisces back into the day when he, his cousin and a friend started their own street fashion line.  Canadian born Jack grew up in a West Indian home in the suburbs of Scarborough, Ontario with his two older sisters’, little brother and mother.  “I was always interested in the fashion, because it was something that was part of my household, growing up my sister pretty much enjoyed making her own clothing and my mom used to make outfits for my sisters, says Jack. I was always just around the culture of design.” His interest peaked in high school, when he started to experiment with fabric paint and silk screening by branding his jeans, baseball caps and t-shirts with dance crew names of the West Indian countries, (St Vincent and the Grenadines and St. Kitts) he proudly represented.  Once he graduated from college, John decided to take an entrepreneur course through Human Resources Development Canada, where he attained his certification in entrepreneurship.  He teamed up with a family member Ramon Charles to brainstorm on ideas of the company’s vision. “We wanted to figure out what angle, to take on a creative level to have people enjoy what we have, but to have some sort of meaning behind it.”  Jack said.  Wanting to separate their brand from the already existing brands at the time like Sean John and LRG, they did not want to be pigeon into the same category which they found generic.  So they collectively decided create a t-shirt line that would be a little bit gritty and urban but exclusive to their consumer. With John’s business savvy, his cousin Ramon’s fashion arts background and Ramon’s fellow classmate Stewart Lee, a graphic designer, the budding young professionals pulled together their business plan. “There was a lot of hours that was invested ,we would break out all our sketches and paper work [and] realize we did not have money to create samples,” says Jack. With an impressive business pitch the three were granted their first business loan, a line of credit for $10,000.  

Loop Apparel launched in 2001, a street fashion company that consists of out of box designs combining arts, culture and music.   Retailers in Japan and Toronto carried their product and the demographic was geared towards the urban downtown market, which later expanded beyond their target consumer shoppers that range from ages 10 to 60 years old.  The company reached its peak of success in 2003, when Loop Apparel decided it would be good time to expand the brand by allowing other investors to partner with their company.  “Being young and not aware of certain legalities and knowing who to trust and who to involve in the company; definitely put me in a bad situation,” Jack reflects.  As the investors were not on the same page their intentions came off as a quick hustle or just a lack of understanding of the company’s vision.  “When there is a great idea that is lucrative, you get people that will convince you, they are in agreement of what you want to do,” says Jack.  By 2005, Loop Apparel decided to close up shop; the three young entrepreneurs’ felt it was time for them to pursue other avenues as running the business took a lot of time and money which they were slowly starting to run out of.   When asked if he would do it all again Jack replies “For sure, but I would definitely seek out a mentor to help me build my company to a much sustainable level, Jack says. You never lose your creativity, what you do lose sometimes is your drive, your creativity will always be there.”