I was at a meeting recently with a couple of colleagues in the men's wear world, two impeccably dressed guys in jackets and expensive leather shoes. One wore an immaculate blue sport coat with white buttons, a yellow tie and spotless suede bucks, with a two-tone Rolex glinting subtly under his crisp white shirt cuff. The other wore a perfectly tailored pinstriped suit (the pants held up with button-fastening suspenders), vintage gold watch and an Italian silk tie. Every part of their outfits was considered. Despite feeling good about my jeans and chambray buttondown ensemble when I left the house, I now felt shabby by comparison. A few years ago, when tailoring and classic men's wear were at the height of trendiness, all the fashionable guys were wearing blazers and skinny ties. Now Don Draper is out, Yeezy is in, and the act of putting on a suit by choice has taken on a new significance. For guys who still choose to wear a suit every day this isn't a style statement, it's a mix of strategy, philosophy and propriety.
"I believe that you should dress seriously if you want to be taken seriously," says Matt Harrell, a Los Angeles-based personal assistant. When I started to think about the idea of men who choose to wear suits every day, he was one of the first people to come to mind. You may remember Harrell from Lindsay, the Oprah-produced train wreck of a docu-series about Lindsay Lohan. As Lohan's PA he featured prominently in the show; ashen-faced and sleep deprived, he attempted to avert one crisis after another for the star. Harrell's coolness in the face of chaos was noteworthy, but his uniform of a fitted black three-piece suit was more so – a striking contrast to the army of denim-clad paparazzi, handlers and hangers-on that surrounded Lohan at every turn. While Harrell and Lohan have since parted ways, the reasoning behind his uniform of fitted black suits remains unchanged. "When you're working for celebrities and representing them, I believe you should give them the respect of being a true professional," he says. "How you dress and carry yourself is part of that."
Every man I spoke to on the topic had a different set of reasons for dressing up, but the ideas of respect and professionalism were ever present. "Not to sound cheesy, but I think you have to dress for the position you're looking for," says Adam Dermer, a newly minted account coordinator at a Toronto communications firm. Dermer is 23, but he forgoes the streetwear favoured by many of his peers for a more traditional, tailored approach. Dermer's workplace is a casual one but he opts to wear a rotating selection of suits, sport coats and leather-soled shoes.
"I think there's a sense of maturity and work ethic that is embodied by the clothes that you wear," he says. "You can wear Zanerobes and a T-shirt to work if you want to, but at the end of the day you're dealing with clients and co-workers that are forming an image of you. If you're dressed like a high school student then they may treat you like that."
I have experienced the power of a really good suit and it truly is something that must be observed firsthand to be fully understood. People stare. Strangers give you compliments. The difference is palpable. There's no doubt that this is part of the suit's appeal, but for some the biggest factor is less obvious.
"I don't dress for other people, I dress for myself," says Bo Yang, a former investment banker who now runs his own commodities trading house. Yang, 29, travels the world for business and takes tailoring as seriously as he takes his work. Among the dozen bespoke suits in his closet are garments made by Lorenzo Cifonelli in Paris, Savile Row's Chittleborough & Morgan, and Sr. Francesco at Toronto's Leatherfoot Emporium. Yang buys the best he can afford and expects his suits to last at least a decade. As such, he favours classic silhouettes in muted tones, nothing flashy or trendy, just masterful tailoring and superlative quality. If you were to ask, Yang could certainly hold forth at length about the things that make bespoke suiting worth the premium, from the way the fabric is cut to the stitching on the buttonholes. He is a man for whom the details, even the ones invisible to everyone else, are everything.
"If people can't tell my suit from a suit from Harry Rosen or Zara, even, I don't care…I know the difference," he says. "A bespoke suit is for the wearer. It's not for the people who look at it."