A “casual” dress hat from Leon Drexler


Sporting my first Leon Drexler hat in Milan, November 2015.

When I first visited Milan, I was prepared to feel like an outsider. I fully expected that my clothes and my manner would tag me as foreign. Instead, in some ways, I felt more at home than I do in Toronto. The main reason being style. Not only did a lot of men wear good leather shoes, overcoats, suits and ties, they wore dress hats (what many people here call “fedoras” and people there call “Borsalinos”). I was finally, for the first time in my life, not the only guy on the sidewalk or the subway platform in a dress hat. And more importantly, no one looked at me askance or openly mocked my hat.

It may come as a surprise but I regularly get comments around Toronto when I wear a hat, often negative. No matter that my fellow citizens are decked out in a cavalcade of outlandish and extreme fashions. I’m the one who gets called “Dick Tracy.” But not in Milan. There, I was just another well dressed guy. And that’s when it hit me: men in Milan wear hats because other men in Milan wear hats.

Despite how challenging it is to wear a dress hat in Hogtown, I simply love them, love the way I look in them and appreciate their practicality and usefulness: something that keeps the snow, rain and sun off my face, while keeping my head warm and looking elegant at the same time. And, despite already owning many hats (three Leon Drexlers, a vintage Biltmore and two Panamas) I saw a gap in my hat wardrobe. I’m well covered in the dressier realm in winter and the casual realm in summer, but I wanted a hat I could wear year around that was as casual as I could envision.


For this, my mind went to brown and soft. Brown, because of its country association, feels casual to me. And soft is always more casual than stiff. The challenge I gave my friend Stephen Temkin of Leon Drexler was to make a hat soft enough that I could bang it into any shape I wanted (instead of having a shape steamed in, as is usual). This is a bit tricky with beaver, Stephen has told me, because it needs to be thinned to achieve softness which can affect its stability.


I choose Stephen’s “Bourbon” colour which he tells me is his least popular brown. It’s on the reddish side and has the perfect outdoorsy look for me. I also wanted a ribbon that didn’t contrast in colour and was thinner than I normally get, with no side bow (only a minimal tag at the back) to again look more casual. And a slightly wider brim (2¼” instead of my regular 2″) for a sporty look. Stephen and I choose the crown shape carefully because the hat needs enough height to allow bashing while also the right taper.


I love the result. To paraphrase an old Stetson ad, the nonchalance is built right in. No matter how I bash the hat, it looks anything but formal (to my eyes anyway – I’m sure the average Torontonian would still see it as a top hat). I’ve quickly settled into a shape I like: squared at the back of the crown with a simple split in the front. No front pinch.


The crown is so soft, in fact, that it feels more like a toque when I put it on. I can easily shape it and push the crown down and the edges together. As hoped, the crown is less pronounced than on my other hats. Less “haty.”

And I suppose that’s where all the pressure I feel from fellow Torontonians has impacted me. As much as I like wearing hats, I don’t like sticking out that much. Or being mocked. This hat is my attempt to be less bold, less conspicuous. And while that is in keeping with my desire over the past few years to steer my wardrobe in a more understated direction, I am willing to admit that conformist pressures have an effect on me.


However, I will keep wearing hats. And one reason is that truth I discovered in Milan. My hope is that perhaps one guy, seeing me in a hat, will feel a little emboldened to try it himself. And to be honest, even if it’s not a hat, even if it’s simply to dress a little better tomorrow than he did today, then my job is done.