Penny Arcade Vintage
By YP Contributor

A lifelong passion for thrifting turns into a profitable business

Rachel Sheehan was only 12 when she visited San Francisco’s iconic Wasteland vintage store for the first time, but she can remember the moment like it was yesterday. Portishead flowed through the store’s speakers and the woman behind the cash captivated her. Rachel only bought a Betsey Johnson satin skirt that day, but it wasn’t the only thing she left with.

“I remember being like, ‘Wow, I’d like to own something that is as inspiring to me as a place like this,’” she recalls. “I just thought it was amazing. It was kind of magic.”

It’s this emotional connection to the past that drives Penny Arcades curated collection of vintage classics, many of which are rooted in the decade that Rachel lived out her adolescence and early adulthood in. It’s become the Dundas West go-to spot for lace-up boots, chunky ’90s shoes, thick wool sweaters, Coach purses, cloaks, sterling jewellery, earth-toned floral onesies, and, of course, the perfect little black dress.

“I’ve been interested in vintage and antiques since I was a child,” says Rachel. “I knew from really early on that I loved the thrill of the find.”

I knew from really early on that I loved the thrill of the find. - Rachel Sheehan, owner
Penny Arcade - Clothing, jewellery, swimwear

Cheap thrills and local treasures

In the early 2000s, Rachel’s hobby turned into a business when she got what she calls her “sea legs” selling clothing on eBay. In 2008, she opened Penny Arcade, naming it after an arcade that she had frequented as a kid with her brother. “I loved naming it something that had a sense of nostalgia,” she says.

Several days a week she goes thrifting, visiting dealers, church bazaars, second-hand stores and digging through Buy the Pound warehouses. “I have a list of sources that I’ve been amassing for years,” she says.

In addition to thrift finds, you can also find locally produced lines at Penny Arcade, including Bully Boy lingerie and Minnow Bathers. Rachel’s particularly proud to carry Filly and Foal, a line of children’s vintage wear, which is tucked into a small wardrobe at the back of the store.

Penny Arcade - Clothing, jewellery, swimwear

It’s not how it looks; it’s how it feels

Rifling through the racks, it’s hard to ignore the handwritten messages on each item’s price tag. “Roar!” reads the tag on a leopard print dress, making it hard not to envision exactly what the dress looks like on. On a black DKNY wrap dress, the tag reads, “This dress is like the platonic ideal of a great black dress.” And on a Pierre Balmain black blazer with black pearl buttons, “If you like this ’80s Balmain piece on the hanger, wait until you try it on. Just wait.”

“I love writing the tags. Because vintage is subjective. There is always something you can say about every piece and it elicits such a different response,” says Rachel.

It’s this careful detail that makes it clear that Rachel understands how clothes feel. It’s not just their tactile nature, but also the emotional connection they can evoke and how the perfect vintage find can feel just a little bit magical.

Penny Arcade - Clothing, jewellery, swimwear
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