Jason Pillay was that kid in school who never shied away from self-expression. “I was always dressing up,” he laughs. “I’d show up in head-to-toe monochromatic looks. It just came naturally to me.” His childhood style hinted at a creative path ahead, but it took time for him to realize fashion could be more than a personal passion.

“After high school, fashion was always there, but I didn’t know I could turn it into a career,” Jason says. He worked in retail for a while, including jobs at Old Navy, H&M, and Nordstrom, but felt he needed a more solid foundation. “I wanted to learn more about the industry and get an academic background,” he explains. That’s what brought him to JCI.

Jason chose JCI for its vibrant Gastown location and because he’d heard great things about the instructors. Initially, he imagined himself in buying or PR. But once he got hands-on experience in the program, he fell in love with styling. “I remember participating in four mixers while I was a student. Those were such great opportunities to meet photographers, models, makeup artists, and hair stylists—people you’d need to do a shoot,” he says. “A lot of them would say, ‘Hey, would you be interested in working on something outside of this?’ That’s where it really started.”

From there, he dove into a self-described “photo shoot summer,” determined to build his portfolio. “I remember having just one photo shoot in my book and thinking, ‘Oh my god, I only have one shoot!’ So I committed to getting more.” He even launched a free website while still in school, eager to put his name out there.

What Jason quickly discovered was that the glamorous image of a stylist—portrayed in movies and magazines—was only part of the story. “I wasn’t prepared for what I had to do after graduating,” he admits. “I spent a lot of time Googling stylists. It looked super glamorous, and that’s what drew me in. But there’s so much more to it.” These days, he’s learned that styling involves a ton of behind-the-scenes hustle: sourcing, prepping, returning pieces, negotiating rates, talking to PR companies and agents, sorting through expenses—an endless swirl of admin work that’s as much a part of the job as the final look on set.

“I’m glad I can talk about it because nothing is all glamour,” Jason says. “And I don’t see it as a downside—there’s just so much hard work that goes on behind the scenes. That’s what leads to the more glamorous moments.” He’s been self-represented his whole career, which means he’s always had to negotiate his own rates and build out supportive structures from scratch. “It’s a lot of work, but it’s also really rewarding,” he says.

One of the biggest lessons Jason’s learned is the power of community. “I have a lot of friends who are stylists, and we’ve all had different journeys,” he says. “We mentor each other and learn from one another. Everyone has their ups and downs, so it’s important to have people you can reach out to—like co-workers, but different because everyone works for themselves.” That supportive network has been key to navigating an industry where many people work for themselves.

Reflecting on his JCI experience, Jason credits instructors like Joan and Melanie for inspiring him. “Anytime I see Joan, my heart melts,” he says with a smile. “She was so present when I was in school—her experience, her encouragement, the advice she shared. She really left a mark on me.” That mentorship planted seeds that Jason continues to pay forward, collaborating with fellow JCI grads and using his connections to help others get their start.

He’s also quick to emphasize the importance of just showing up. “When I was at JCI, I put my hand up for every single event,” he says. “I volunteered for almost everything. Sometimes I was just sitting backstage taping shoes for eight hours, but in those eight hours, I was meeting all these models and talent. I was building my network as I went.” For Jason, success in styling has always been about proactivity—being willing to take chances even when there are no guarantees. “You don’t just show up at a photo shoot,” he says. “There’s so much prep involved, and it’s very hands-on. It’s a trial and error process, and that’s okay. That’s where you learn.”

This philosophy of adaptability has taken Jason into many different corners of the fashion world. Known for his eccentric and artistic style—“very out there,” as he puts it—he’s had plenty of opportunities to bring bold, fashion-forward visions to life. But he’s also learned how to balance that creativity with the needs of commercial clients. “When you’re working with brands, it’s about their campaign, their message,” he explains. “It used to be a challenge because people saw me as the super fashion-forward stylist, but I’ve shown that I can do the corporate, everyday-wear jobs too. Versatility matters.”

That versatility has led him to expand into costume design for film. “I’m 50 percent stylist, 50 percent costume designer now,” he says. “I like that it keeps me in the industry and lets me wear different hats. If you want to sustain a career as a stylist, you have to be adaptable.”

One of Jason’s career highlights so far has been styling an artist at the Juno Awards. “It was one of the biggest jobs I’ve ever taken on,” he says. “It was surreal and definitely a milestone moment.” The project involved styling a musical group—two men and one woman—plus seventeen dancers, choir members, and band members. “It was a whole production,” he laughs. “There was a lot of communication and prep—five weeks of it, for one day. But it was super fun to hear the artists talk about their vision and the story behind their music, and then translate that into fashion.”

He even brought in two fellow JCI grads, Cheyenne and Rowena, to assist with the project. “All three of us went to the same school, which is crazy,” Jason says. “We were all in different classes and somehow, we’re still connected.”

Beyond the bright lights and the cameras, Jason’s work is grounded in a sense of purpose and community. Outside of styling, he’s a board member at Sher Vancouver, a non-profit dedicated to supporting queer South Asians and their allies through arts, culture, and social services. “Aside from all the work stuff, I just like being a regular person,” Jason says. “Hanging out with friends, exploring Vancouver, eating at new places—there’s so much to discover here.”

In a world that can often feel cutthroat, Jason’s journey is a testament to what can happen when you embrace vulnerability, say yes to opportunities, and let curiosity lead the way. “It’s hard to answer when people ask how to get a job like mine,” he says. “There are so many layers to it. But you’ve just got to start where you are right now. Don’t think too hard. Meet people. Try things. Build your book up. That’s how it begins.”