Where to get a custom hat in Toronto

This has probably happened to you, if it ever crossed your mind to try wearing a dress hat: the only thing you could find was a cheap, poorly made fedora that didn’t fit right and when you put it on your head, it looked dumb. You decided from then on that you look bad in hats.


But Stephen Temkin knew better. He ventured out several years ago to get himself a good hat. He couldn’t find one. So he decided to make one. And that’s how Leon Drexler began.


Before I go any further, a bit of a disclaimer. Stephen and I have been friends for a while, since I did a feature on him for CBC Radio’s Metro Morning. While getting my first hat, we discovered a shared interest in all things sartorial, as well as a love of cigars and fine libations. However, Stephen has in no way compelled me to write this article – I am doing it solely for those guys who want to wear a hat but can’t find a good one.

My first Leon Drexler hat, a Gaffer in an un-dyed natural tan with greenish-grey band.

My first Leon Drexler hat, a “Gaffer” in an un-dyed, natural tan with greenish-grey band.

“Leon Drexler” is a combo of Stephen’s father’s first name and his mother’s maiden name. Stephen decided to give the hats a brand because, as he says, “sometimes you start things and you end up not being the person finishing them.” In other words, Stephen wasn’t sure if the company would continue someday, somehow without him, so he wanted it to be its own entity. Plus, “Leon Drexler sounds like an old Jewish hatmaker.” Stephen has spent the last several years collecting the equipment for hatmaking as well as building the skills and knowledge for different kinds of shapes and finishes. And he’s done it all himself: Stephen has never apprenticed or taken a hatmaking course. In fact, he’s never met another hatmaker in person.

Remarkably, and Stephen wouldn’t say this himself, in very short time he has become one of the world’s best hatters. He is, without debate, Canada’s best – partially because he is the only exclusive maker of men’s dress hats left in the country. We Torontonians are lucky enough to call him our own.

Stephen working on the finish of a hat.

Stephen brushing a hat to achieve the desired finish.

Stephen works out of his home near Dundas and Dovercourt. He has two studios: his basement is set up for shaping and pressing hats, as well as working on the finish. In his attic, Stephen does the sewing of linings and bands. And his house is where prospective local clients have their consultations.

Getting one of Stephen’s hats goes something like this: At your first meeting, Stephen carefully measures and re-measures your head. Then, the hard part, picking the shape and colour of your hat. This can take the better part of an hour because there are so many options: tall or short, wide or thin, the size and colour of the silk ribbon, even the exact way the crown of the hat is dimpled. Thankfully, Stephen brings his vast knowledge of tailoring and all things sartorial to the decision, insuring that your hat will be a congruent part of your wardrobe.


Recently completed mustard yellow Forager for a US client.

Then you wait, typically 8 to 9 weeks, for your hat. In that time, Stephen receives the raw, unformed beaver hat from his supplier, in the colour you requested. That’s followed by weeks of shaping, blocking, steaming, finishing and lots of sewing. The part of the hat that is truly made for your head is the leather sweatband: it is cut to exactly your circumference. The hat is then blocked to the closest size that matches that sweatband. The average price for one of Stephen’s hats starts between $490 and $600, depending on the complexity of the hat.

Stephen pressing the brim of a hat into shape.

Stephen pressing the brim of a hat into shape.

Stephen tells me that his biggest demographic is guys in their 40s and older. A lot of his customers are local, but he receives plenty of orders from the US and overseas. Increasingly, he is getting repeat customers. That’s certainly my story: shortly after getting my first hat, I knew I needed another. It fit so well into my lifestyle and wardrobe, I became a hat person. It now feels strange to leave my house without one. But life gets boring without diversity. For my second Leon Drexler, I went with something more flamboyant, a Homburg-style that I can wear in more formal situations, or when I’m just feeling a bit dandyish.

Leon Drexler homburg-style hat in slate blue. Note that the ribbons on the crown and brim are slightly different colours.

Leon Drexler homburg-style hat in slate blue. Note that the ribbons on the crown and brim are slightly different colours.

Like me, most of Stephen’s customers already wore hats before coming to him, but off-the-rack. And like me, many guys have large heads and thus difficulty finding hats that fit properly.

Sadly, there is no way to talk about dress hats without confronting the elephant in the room, that “men don’t wear hats any more”. Nonsense. The issue is that most men don’t dress well any more, and a dress hat looks stupid with a tshirt and jeans. But, as some men are starting to pay more attention to their wardrobes, the dress hat is coming back. In fact, just in the last few years Stephen has noticed more of them on the streets. “Nobody is surprised to see a man in a hat any more,” he says, adding that recently “acceptance of hats has come back.”

Contact Stephen for an appointment through his website, Leon Drexler.