Dundas Street thrift shop Expo Vintage has just added an extra splash of colourful vintage clothing and houseware to its stock, courtesy of the New Zealand thrift mavens behind pop-up shop Silly Billy Vintage. The brand is known for a curation of playful pieces, including cottage core and western aesthetics, as well as ’80s glam.
“We always try to find pieces that are true to our brand and that we would essentially wear ourselves,” says co-founder Evie Davis.
Her and counterpart Sydney Reynolds are best mates (and roommates) from New Zealand, who met in Toronto when they were introduced by a mutual friend in 2018.
“Once we started hanging out, we realized how much we had in common and then a year later, we moved in together,” says Davis.
They were both long-time thrifters, Reynolds having picked up the habit from her father — who brought her to “op shops,” also known as thrift stores, back home.
“They were so exciting because you never knew what you were going to walk in and find,” she said. As a young adult, she bought her clothes exclusively second-hand because she appreciated the affordability and uniqueness of the finds.
Meanwhile Davis had been working in retail, and found herself more and more frustrated with the unsustainable practices involved in clothing production and sales. During university, she began her own practice of selling second-hand clothes through Instagram.
Together they bonded over their shared passion for thrifting, and playing dress up, which paired perfectly with Davis’ photography practice. A year into living together, the pandemic hit, and they were both struggling to secure full-time work, so they began selling clothes from their personal wardrobes outside of part time jobs.
“Silly Billy was really just a natural extension of that,” Reynolds says.
They began using the Instagram account that Davis had previously sold second-hand clothes from, and rebranded it as Silly Billy.
The name was inspired by their shared cat Billy, who Reynolds had inherited from a regular customer while working at Wanda’s Pie in the Sky. At the time she had been spreading the word that a cat would be a perfect complement to her home, and then just like that, two-year-old Billy was dropped at their door.
“She had a different name, but once she came into our home we renamed her Billy because it seemed more fitting for her personality and the vibe of our household,” says Davis. “She was great, so silly and had such a big character; a bit of a weirdo, and a great companion for us during the pandemic.”
During the summer 2021, they left their part-time gigs to pursue the business full-time.
“We realized we wanted to work for ourselves and that if we put more time into it, we’d get more out of it,” says Davis. They started vending at the Hippie Market, and hosting backyard pop-ups at their home.
“That was when we realized there is actually money to be made in the vintage scene here,” adds Reynolds. So they started selling wholesale, and curating larger collections.
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In 2022 they rehomed Billy with a friend, packed up their lives and business, and moved back to New Zealand together. Inseparable at this point, they lived together once again and decided to pursue Silly Billy in their local market.
They were still shipping to Canadian and American customers while traveling around New Zealand to host pop-ups and participate in markets.
“I feel like Toronto likes vintage more than New Zealand, but New Zealand loves thrifting (and has a healthy market scene),” explains Davis, noting that their Toronto and general North American influence helped them stand out against competitors.
“We were bringing over cottagecore and Western aesthetics, which weren’t big over there at the time. When we moved back, it was a lot of streetwear and American vintage,” says Reynolds.
In 2024, the pair returned to Toronto and immediately sought to re-establish Silly Billy in the vintage scene. They spent a month readying themselves — sourcing new stock, securing rolling racks, coat hangers and business cards. Then they did a couple of Instagram drops and vended at the Hippie Market and Sunday Variety, before encountering a long-term opportunity that was too good to turn down.
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“My partner saw that Expo was looking to rent out either their basement or their backroom, so we just went and had a look, and then we basically agreed to it that day,” says Davis. “We had to move fast — I feel like in Toronto you have to just say yes and go for it.”
The plan is to stay there as long as they can, using the summer as a trial. They aim to be as inclusive as possible with both sizing (women’s XS- 3XL) and prices. Apart from rare pieces, their prices range from $20-$45.
Silly Billy Vintage is located in the back of Expo Vintage, at 1250 Dundas St. W., from 12-7 p.m. every day of the week.
Jeremy Diamond is a lawyer and member of both Ontario and Florida Bars. Jeremy practices in the area of Plaintiff personal injury litigation. Click here to learn more about 
