Hippie Market

Toronto’s hottest new outdoor vintage market is where all the cool kids are going

If you visit 1200 Dundas St. W. at just the right time on just the right night, you’re in for a treat. What was once a Beer Store parking lot is now filled with stalls housing various vintage pop-ups; instead of strewn shopping carts and bags of long-emptied beer cans, the space is now filled with people dressed in outfits that belong on the front of a trendy streetwear magazine. Tonight, it’s hosting Hippie Market, a nomadic vintage pop-up market beloved by the cosmopolitan, chic, and environmentally-conscious.

At the entrance closest to Ossington, there’s a woman reading tarot cards at a small table. If you venture further, passing the group of models dressed like they’re straight from the 70s—complete with thick moustaches, tinted aviators, and flared pants – you’d feel welcomed by the music drifting in from the speakers, floating about the energetic conversations happening all around.


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The first stop: Clutter Porch, a pop-up filled with “fuzzy, funky, colourful, soft, sparkly things” curated by Jo Kolakowska. Donning a denim coat trimmed with repurposed white vintage fur and a cowboy hat, Kolakowska chatted eagerly as she simultaneously attended to customers. After her bartending gigs ended due to the pandemic, Kolakowska returned to her old professional stomping grounds. (Back in high school, she ran a vintage reselling business with a friend of hers called Schmoe’s Clothes, a name at once riotous and adorable).

Kolakowska was in Guatemala when the pandemic first hit, staying at a hostel where she coincidentally met another woman who happened to be from Toronto. Once she learned about Clutter Porch, this friend, “who knew Kealan, the organizer of Hippie Market,” encouraged Kolakowska to reach out and set up shop at the next event. From then on, Kealan loomed as a mythic figure; everyone gushed about her, speaking with true, reverential admiration.

The Kealan in question is Kealan Sullivan. As soon as you speak with her, you’d know exactly why she draws such veneration. Her calm, confident voice radiates outward and makes you feel like you’re talking to an old friend. Hippie Market is her latest vintage incarnation, which she runs with her partner Alistair Kyte.

“People always came to me to find out where they could get almost anything,” she says. From 2004 to 2016, Sullivan owned a smattering of vintage stores around Toronto: 69 Vintage, Buy the Pound and V, to name a few. She’d always run the occasional outdoor market at her stores, so this was a natural next step, pairing her entrepreneurial savvy with her love of fashion.

“My personal style has always been very much a part of who I am. And I never looked outward,” Sullivan says when asked about her fashion influences. This same individuality is what drives Hippie Market, making it a truly unique experience. She calls the public’s newfound interest in vintage “a massive resurgence,” though she doesn’t balk at the idea of calling it a trend. “It’s definitely a trend.”

Sullivan credits sustainability and inclusivity as the two major themes of the market, both which are apparent as soon as one steps foot onto the asphalt Hippie Market inhabits. Clothing manufacturing is one of the largest production industries in the world, right behind automotive and technology manufacturing, single handedly creating 8-10 per cent of global carbon emissions. Due to a lack of recycling and mindful use, tonnes of garments become unnecessary waste on a yearly basis. “There’s been a lot of awareness about sustainability—that has been the best trend of the last few years. People [are] really starting to appreciate the labour involved with making clothing. I mean, the waste that comes from the garment industry, that’s a very real thing,” she says.

Sullivan says that making Hippie Market such a welcoming and inclusive environment mostly arose naturally. She has a hand in determining the placing of vendors throughout the market, almost like a seating chart, and she often pairs less experienced vintage sellers with those who have been in the industry for longer, creating a feedback loop of advice and casual mentorship. “We’re very available to our vendors,” she says of her and Kyte’s presence at the market, “in order to make them feel comfortable and safe and proud of what they’re doing.”


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“Everyone is so nice, so supportive. People will send down [customers] to other stores, like ‘Oh, you’re looking for this? Go to this person!’” Cassandra Gemmell says. Gemmell runs The Preston Style and Critical Femme Archive with her partner Chelsea Preston. Their outfits don’t necessarily match per se, but they are complementary of one another, and this compatibility extends to their collaborative vintage venture. While Gemmell’s style gravitates towards “classic, very diverse fashion,” with a hint of drama, Preston’s is a mix between “cottage core fantasy” and garments that are “very, very queer [and] gender free.” The supportive bonds between vendors isn’t the only means of inclusivity here at Hippie Market. “I try to have sizes extra small to four XL. I’ve tried to be size inclusive, because that’s really important to me,” Preston says.

Sullivan has big plans for Hippie Market, so big that she can’t even share them with me. “I just want to continue having a really strong, authentic brand. We have a lot of really dedicated people, so I want to create that message and continue to help each other out.” Though it’s unclear how long Toronto have to wait for the next phase of Hippie Market to come to life, it’s clear the hundreds of vintage lovers who keep coming back for more would happily wait a lifetime.

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