Inside Jonathan Cavaliere’s Journey From Menswear Influencer To Custom Designer

He was in Italy, having lively and productive discussions with potential manufacturing partners, when Jonathan Cavaliere dared to make an unthinkable request.

This was, in some respects, a critical moment a career journey that is somewhat unique in Canadian men’s fashion — from the front lines of the retail sector to the expansive landscape of social media to the launch of his own custom-designed brand. 

“We sat down, talked about fabric and construction, silhouettes, and it was going great,” Cavaliere recalled in a recent phone interview with Menswhere.

“As soon as I said I wanted to take out that shoulder pad, the conversation changed. It went from ‘Yeah, yeah, yeah’ to ‘No, we can’t do that.’”

Cavaliere knew otherwise, just as he knew why those shoulder pads had been put there in the first place. Outside of bespoke tailors, a lot of what gets shown on the racks in many menswear stores are jackets filled with padding intended to hide imperfections. It also gives some “buffer room” to offer a generalized size for the majority of men.

All images courtesy of Mr. Cavaliere

As he’s grown his eponymous brand, the man behind Mr. Cavaliere has placed his bet on the soft shouldered jacket. And with the world slowly re-emerging from the COVID-19 pandemic, it looks even more like an idea whose time has truly come.

“Everyone’s been talking about the casualization of the workplace, and what that’s going to look like,” says, Cavaliere, who also hosts the How I Suit Up podcast. “People say that guys aren’t going to be wearing suits anymore. My quick answer is it’s a good thing that the guys who don’t want to wear suits don’t have to. But the the ones that do now have the opportunity, and the creative options, to wear the things we want to wear.”

The results can be seen in Mr. Cavaliere’s Spring Summer ’21 collection, which doesn’t fixate on the soft shouldered jacket so much as make it a foundation for a highly versatile ensemble. This includes not only suits and ties but plenty of knit polos and trousers with side adjusters and rubberized waistbands.

From the Mr. Cavaliere Spring Summer ’21 Collection

“I can’t see anyone working in one place anymore, and that means they’re going to need a very flexible wardrobe,” Cavaliere says in reference to his target customer. “He’s going to be a more mobile guy — someone who can work from his phone, who’s travelling, who’s exploring the world and wants to look good while doing it. Guys are celebrated when they dress up.”

From Canada’s Sharpest Man To Manning His Own Brand

Though the development of Mr. Cavaliere is hardly an accident, it also wasn’t an inevitability. After fashion school, Cavaliere got hands-on experience with the industry by working at Grafic, a luxury goods and clothing provider based in Vaugh, Ont., as a personal shopper and buyer. 

“The clientele there wasn’t super old — many would be in their 40s — but at the time, being a younger guy at 21, there was a sense I was able to be the fresh eyes on the scene,” he said. “I dabbled in a little bit of everything, and it let me get a pretty good sense of what the industry was about and see what I was really interested in.”

While still working at Grafic, Cavaliere’s early efforts in posting fashion and style content on social media paid off big-time, when he was named Canada’s Sharpest Man by Sharp Magazine and Hudson’s Bay Co. in 2012. The increased profile made Cavliere an influencer before the term became widely used. 

With Instagram’s meteoric rise still in its infancy, Cavaliere parlayed his exposure into his own blog, which became akin to a fashion magazine in its own right with detailed tips and tutorials about the art of dressing well. He was soon a frequent guest at brand launches, parties and other stops on the Canadian fashion and style scene.

“That was the point where I hit a crossroads,” he admitted. “I was thinking of leaving a relatively safe job. . . when I left, in my head my thought was that if I run the blog full-time, I would have to do it properly or not do it at all.”

Being an influencer, of course, means getting to try on a lot of different brands, and Cavaliere still remembers the first time he tried a Neapolitan jacket on for the first time.

“I remember thinking, ‘This is what tailored should be,’” he said. “A super-soft shoulder, very supple, something that moves with your body. That was the initial start of my thinking that tailoring could be more than structured shoulders and lapels.”

As a brand, Mr. Cavaliere’s other core pillars include responsible manufacturing and personalized service. Whereas influencers are usually focused on creating content that’s aspirational, Cavaliere now sees his mission as making quality men’s fashion more attainable.

“Usually when customers walk in they’re relatively nervous. Almost 70 per cent have never had a custom suit before. They’re not exactly sure what to do,” he said. “The magic is when the final product comes in and they throw on the garment for the first time. They come and they throw on the jacket and pants, look at themselves in the mirrors, and it’s like you’ve changed them. I like that I get to do that every day.”

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