These are highlights from a conversation first published by Joshua Geniole in Officina Geniole Weekly, shared here with his permission. Photos courtesy of Officina Geniole.
My friend Josh Geniole writes Officina Geniole Weekly, a letter on culture, craft and the good things in life. This week he did something a little different and sat me down to talk about how Mr. Cavaliere began, what I've learned from years of fitting men, and why dressing well still matters. Here are a few of my favourite moments.
From Josh's Introduction
I first met Jon nearly ten years ago, when he would come into my barbershop. We hit it off right away, as if we had always known each other. Since then we have developed a strong friendship, often meeting for coffee or lunch, wandering through endless shops and aisles at St. Lawrence Market, discussing life, business, and inevitably, tailoring.
What sets Jon apart isn't simply his eye for a well-made suit or his appreciation for fine fabrics. It's his knowledge, attention to detail, and genuine commitment to taking care of his customers. He gives his clients a true one-on-one experience, he gets to know you and brings out what you are looking for, even if you are not sure of what that might be. The truth is, he understands that dressing well is more than the actual garments themselves. It's about how they make you feel, and the confidence that comes when you present yourself to the world in the right way.
How did Mr. Cavaliere begin, and what made you want to get into custom menswear?
My love for menswear started when I was eight years old. My family and I were invited to a relative's wedding, so my mother had inquired with my aunt about a hand-me-down suit from one of my cousins.
I vividly remember putting on the pants and the shirt, and having my mother tie my tie. As we headed out the door, I threw on the jacket and caught a glimpse of myself in the mirror. For the first time in my life, I felt like a man.
As I walked outside, my sister uncharacteristically opened the car door for me, saying "Mr. President." I laughed, jumped in, and slid over to the passenger side, only to jump out at our destination while repeating her gesture. As ordinary a moment as it may have seemed to my parents and sister, I became unconsciously infatuated with that feeling. For the first time in my life I realized that what you wear matters.
That feeling carried me into a career in the fashion industry as one of Canada's leading menswear voices, building an audience, working with global brands, and developing the point of view that drives what I do today. In 2012, that passion was recognized nationally: I was named Canada's Sharpest Man by Sharp Magazine and Hudson's Bay Company, selected by Canada's top fashion editors from thousands of entries across the country. It was the moment Mr. Cavaliere began.
I started Mr. Cavaliere because I wanted to guide men through the sartorial jungle by creating custom clothing that not only looks great but is uniquely tailored to them.
What should a man look for when buying a suit?
Start with the shoulder, because it's the hardest thing to alter. Then ask how the jacket is constructed. A full canvas will mould to your body over time, whereas a glued (fused) chest stays stiff and can bubble. Then cloth: for a daily business suit, a high-twist worsted in the 270–320g range is hard to beat. It breathes, resists wrinkles, and lasts.
More on construction: Understanding Suit Canvas: Structure, Comfort, and Longevity Explained.
What's something about tailoring that most people don't notice, but you immediately see?
The collar. If there's a gap between the jacket collar and the shirt collar at the back of the neck, I see it from across the room. Same with a jacket that pulls into an X at the button, or sleeves that hide the shirt cuff completely. Small things, but together they're the difference between looking well dressed and looking like you're wearing someone else's clothes.
Do you think men today are becoming more interested in quality and craftsmanship again?
Yes, but they're buying differently. They're not buying five suits. They're buying fewer, better things, and they want to know where they came from and why they cost what they do. That's healthy. The men I enjoy working with most aren't chasing trends. They want a wardrobe that works, built over a few years, that gets better with time, and someone they trust to help them build it.
That's the idea behind Wardrobe Architecture.
Want to Read the Rest?
There's more in the full conversation: what was missing in Toronto menswear when I started, what I've learned from years of fitting men, why a good jacket should feel closer to a cardigan than to armour, and where menswear in Toronto is heading.
Head over to Officina Geniole to read the full interview →
And while you're there, subscribe. Josh's weekly letter is worth your inbox.
"If you're in Toronto and looking to invest in a well-made suit, give Jon a visit. You'll be in good hands." — Josh Geniole
Thank you, Josh. If you'd like to talk about a suit, a jacket or a wardrobe that works, I'm at 63 Jarvis Street in Toronto, by appointment. Book a fitting.
