When lateral thinking guru Edward de Bono wrote his best-selling “Six Thinking Hats” he probably didn’t have entrepreneur Jay Cheng in mind. Still, the book that has become a bible for business innovation, anticipates the way Cheng tapped her creative side and followed her passion to the top. De Bono created the notion of six hats as metaphors for the way the brain works in order to enhance business development and planning – white facts and logic, green for creativity, yellow for optimism etc. It is easy to see how Jay intuitively applied this notion and ran with it.

Jay Cheng began her fashion and design career in Hong Kong over 25 years ago and designed and produced a wide range of costumes, wardrobe, and runway shows for film, TV, and live performances. Jay thinks of fashion and accessories as empowering, art and identity and for her, it is also business. She believes that each individual should find their own way. When she and husband Franklin mutually decided to take some time away from their marriage, Jay decided to use the time to get to know herself better. She was determined to find her niche in life. This search took her to her second love – millinery. She realized that this was her calling and one true obsession. As we talk with Jay via zoom, she models one of her elegant creations: “If you choose wisely, invest in good material and make a hat, it will elevate, reveal and amplify your outfit” she says.

The realization grounded her, allowing her to focus her creativity in designing fabulous hats. Cheng had enjoyed significant success in Hong Kong so the decision to move back to Toronto in 2016 wasn’t easy. Still, while life in Canada was very demanding, she knew it was the right decision for her.

Photo by @jesusmazaphoto

In 2008, after Jay and her husband reunited, she learned she was having her first baby and this impacted many aspects of her life but her love and passion for the craft of millinery remained unchanged. “It was hard, dealing with various emotions and being creative at the same time. I was working for myself and running a business, creating hats and having a new baby. I was torn between my family and my work.”

She pushed through this time, with support from her husband, seamstress, mentors and her clients. Three years later, when she had her second son, she was armed with the knowledge of what was to come and things were much easier. To build Jaycow Millinery in Toronto, Jay had to learn how to create a space for herself. Today she says: “Life is a constant balancing act, a series of compromises – but not with the quality of my hats.”

Life is a constant balancing act, a series of compromises

Everything she has absorbed about running a business in North America — talking to clients, budgeting — has been on the job. “I’ve learned from making mistakes,” shares Cheng. Millinery, according to Jay, is a big part of the “Slowmaker” movement. She believes her success is due in large part to the fact that people are intent on becoming more sustainable in their choice of clothing and want to move away from fast fashion. “Consumers understand that a hat bought from a milliner will probably cost more than one that is mass produced, but it will be far superior in quality, fit and will last a lifetime.”

Jay Cheng wearing the The Ma Hat x @callenschaub. Photo by @jesusmazaphoto

Photo by @taranoellephoto

When the pandemic hit in March 2020, it challenged Jay and her team to pivot quickly since in-person modelling was halted. She was not only juggling her business but also her kids who were at home. Thankfully with a super-efficient team, Cheng was able to offer virtual bespoke experiences where she would meet her clients online and create a design based on their wants and budget. She also took this time to redo her website, became more digitally accessible, arranged online fashion shows and socially distanced photo campaigns. Jay says that the pandemic has been a great learning experience. “People talk about businesses pivoting for success – that’s what I tried to do. Like me, my clients are juggling a lot in their everyday lives. At the same time their dress is casual and they need a hat that can take them for walks with the dog or dash to the grocery store, but still lift up their spirits – make them feel like they are putting their best selves forward. My job is to try and help them do that.”

Adventurous at heart, Jay has travelled the world honing her craft. She has learned from some of the best milliners globally, including Waltraud Reiner, a renowned milliner and the founder of Hatmobile, based in Melbourne Australia and Rose Cory, world renowned milliner to the British royalties and teacher. Both of them taught Jay unique techniques and showed her a variety of ways to be the best.

Even though she is a rebel by nature, Jay’s profound respect for traditional craftsmanship has inspired her contemporary take on millinery. In doing so, she has become a teacher of this art. Again, the pandemic forces the cancellation of group classes, but now Jay offers socially distanced and COVID-19 conscious private courses where students can learn to block her signature wool felt hats.

When asked what would be her advice for future women entrepreneurs and business women, she says,

Give yourself time. It’s okay to make a mistake, and most importantly, believe in yourself. Love what you do; only then will you be curious enough to learn more things about your field of choice

Jay’s international clientele includes private hat-lovers, brides, costume designers, and renowned celebrities like Canadian musician Ontario, Artist Glen Baxter and Style Icon JP Michaels. Through her creations, one can experience the past, feel the history, and explore a new avenue of personal expression. Cheng’s hats are handmade artisan hats made of felts, and fur felts. Each piece created is handmade and never fails to challenge and surprise.

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