This Toronto shoe shine business is a side-hustle for a team of mainly female artists

The snowy and salty streets of winter in Toronto have made for good business for one shoe shine company in the city’s downtown.

Penny Loafers Shoe Shine Company Inc., founded in 1994, is made up almost entirely of women who work in creative fields, including actors, writers and musicians, and has three Toronto locations in the financial district. For many of its staff, the job is a “side hustle,” its owner says.

Staff have polished the footwear of thousands of clients, including prime ministers, former premiers, former mayors, and men and women who work in executive suites of banks and law firms, according to the company’s president, CEO and owner, Jenny Young.

Young said she loves how “old timey” the business is and she doesn’t plan on slowing down any time soon.

“At some point every year, in the 23 years that I’ve been doing this, somebody says to me: ‘Oh, this is a dying art. This isn’t going to last.’ And it always has,” Young said in an interview at the company’s shoe shine shop at Fairmont Royal York hotel.

“There is always going to be a need for someone to clean shoes. We all wear them.”

Young, an actor herself, has built a team of creative staff and 10 out of 12 shoe shiners are women. It’s a fact that often surprises clients.

Young said the founder of the business, Penny Simmons, wanted to create a space for women to be able to transition in their lives, either personally or professionally. She said the business gave women a chance to make money while pursuing their artistic passions.

Flexibility is built into the schedule to enable staff to “spell each other off” when they get gig work, she added.

“I’m fairly positive that most people who work for me, I think all, really enjoy it as a side hustle,” she said.

Young said she has dreams of expanding the business into Billy Bishop Toronto City Airport but the goal currently, during the messy winter months, is simply to help people put their best foot forward.

“We’re in a feel-good business. We really, really make people feel good.”

‘In between gigs, you need some work,’ actor, writer says

Christine Horne is a shoe shine valet at Penny Loafers and has been an actor for 20 years as well as a writer who records audio books. She said the work is welcome as she navigates a career in the arts. Horne also runs a small theatre company called Shakespeare in the Ruff.

“I started working here in 2016, I think, and I just needed a job,” Horne said. “It can be a really unstable life as an actor. I do pretty well, I would say, and even still, in the time in between gigs, you need some work.”

Horne said she knew Young and reached out to see if she needed any help. She did.

“I knew a lot of artists worked here. I knew that it was flexible and supportive of artists and the kind of wacky schedules that we can have,” Horne said.

Horne said shining shoes is a tangible skill that involves using her hands and having conversations. She said she enjoys it, calling it a job that’s “unplugged.”

“There’s something very satisfying about being able actually to complete a task and see the result of your work.”