Where to get vintage menswear in Toronto

The first time I came home with vintage clothes, my mother was horrified. I was a teenager and she an old-fashioned Portuguese mom, and the used 1970s loud pants I had bought in Kensington Market were, in her eyes, disgusting. “Who knows if those were ever washed,” she complained, “you could get some kind of rash.”

I bought vintage then for many of the reasons I do now: I wanted good quality clothes at affordable prices; and I couldn’t necessarily find what I wanted in malls and department stores. Also, then like now, I wasn’t trying to perfectly imitate a specific era. I like clothes from the 30s straight through to today and I usually mix and match to achieve the look I want. I have an affinity for fedora hats and collar pins, but I try to stay away from monocles and walking sticks because as elegant as I think they can be, I’m not completely comfortable with my clothes being a costume. I want to look good without drawing that much attention to myself.

Toronto is an excellent city for vintage clothes lovers if you are a woman or are looking for party costumes. It’s much tougher if you are hoping to build a classic men’s wardrobe rooted in the 20th century but with contemporary sensibilities. I have found only three I would recommend, and only one of them is solely dedicated to gentlemenswear.

Kingpin’s Hideaway


Like walking into the closet of an aristocrat who’s fallen on hard times and is forced to sell his wardrobe, stepping into Kingpin’s Hideaway is like stepping into another time. Owner Jonathan Hagey is a walking encyclopaedia of men’s clothes and especially accessories – he can spot an Edwardian lapel vase a mile away. And he seems to have a magical quality that allows him to attract and find the most rare, most unusual and most intriguing of oddities. He scours estate sales with a keen eye – and we are lucky enough to share in the spoils.


Jonathan Hagey (right) with Scott Thompson. Photo: Facebook

What I really like about Jon’s shop is not only that it’s exclusively menswear, it’s that every item is carefully chosen for its quality and classic nature. You can, if you wish, come out of the Hideaway looking like a 1930s dandy – Jonathan has a full stock of pince-nez, watch fobs and top hats. But you can just as easily emerge looking like a – somewhat eccentric – contemporary Dapper Dan thanks to his excellent collection of ties, pocket squares and sport coats.


Jonathan’s shop is indeed a Hideaway, tucked on the third floor of a nondescript building on a quiet downtown street. This past summer, friends of ours from France visited Toronto and were looking for some vintage menswear so I took them to Kingpin’s. They enjoyed it so much, they told me the shop was the highlight of their entire Canadian visit. So give Jonathan a call to set up an appointment and you too will have discovered one of the city’s true hidden treasures.


Kingpin’s Hideaway is located at 309-19 Mercer Street on the 3rd floor, 71 Duncan Street (just south of Queen).

Full disclosure: Jonathan and I have been good friends for a couple of years, even working on projects together, but that didn’t influence this article. I have purchased many items from his shop and truly believe it is the best place in the city for vintage men’s clothes.

Cabaret Vintage


Tao Drayton has been running Cabaret for 19 years. And he is one of the warmest and most gregarious people I know. Every time I visit I get a very sincere greeting, a hug and a heartfelt “How are you?” You may not think Cabaret is a great place for men’s clothes when you enter, but don’t be distracted by the lovely wedding gowns and walls of women’s hats. Dotted throughout the first floor and ammased in the basement grotto is a small but select group of 1920s – 1970s menswear staples like suits, tweeds and tuxedos.


Much of Tao’s clothes are sourced from private estate sales as well as a huge collection of used film and TV clothes. But Tao is taking the vintage market in a new direction, a direction that will increasingly become essential: brand new clothes based on old pieces. Not only can you find a good selection of newly made, vintage-style accessories like bow ties and pocket squares, even cufflinks from Fine and Dandy, but Tao has recently partnered with a local custom tailor to offer new men’s clothes modelled on vintage – including a collection of absolutely gorgeous dinner jackets.


Tao has long been doing this for women’s clothes, especially ball gowns and wedding dresses, but I find it very exciting that he’s applying the approach to men’s clothes. After all, many suits from the 1930s are either too worn or too small to be used by many men today. A new suit, custom made (for a very reasonable price) but with an old pattern? Yes, please.


Cabaret Vintage is located at 672 Queen St West.



Before you enter Gadabout take a deep breath and prepare yourself for complete sensory overload. There isn’t a single surface or wall space not covered in piles and piles of fascinating oddities and trinkets from the past. Clothes are piled high, hats upon hats, rows and rows of shoes, not to mention the shelves and shelves of jewellery, photos, toys and whatchamacallits.


Owner Victoria Dinnick has been at her Leslieville location for 15 years, plenty of time to accumulate. Her secret is travel. Every year she visits Europe, with stops at small markets and fairs in England and rural France. She flies there with empty luggage and returns weighed down with clothes and accessories that have never seen this side of the pond.


I admit that Gadabout’s selection of menswear is reactively slim – just a small collection of suits, jackets and shirts. The eras covered seem to be very, very old (late 1800s) or 1960s and 70s glam, with little in between. The shoe selection, however, is the biggest I’ve seen in the city. The real reason to come to Gadabout are the accessories. I have never seen such a huge and varied collection of men’s jewellery in one place. Not only are they impeccably organized in drawer after drawer, I saw a number of items still in their original packaging.


Gadabout Vintage is located at 1300 Queen St. East.