The oft-portrayed boys club of law and high finance is not without its stereotypes—from Wall Street to The Firm, the style code of urban money has typically been fairly staid, with boxy suits, dressy shoes and an occasional pocket square (if you’re lucky). Working Girl took women out of their steno pool duds and showed them as executives in power suits with big hair—but even that look quickly became ubiquitous, and since the late ’80s, the archetypes of the man and woman who push dollars for a living never really changed. Hair got smaller, sure, and Cashmere Mafia attempted to prove that businesswomen were all this classy, but the combination of a pencil skirt and blouse, or conservative power dressing continued to run rampant into the early-to-mid noughties. These people, who wake up before most people have their first coffee, have always been viewed as conservative dressers, but here’s the thing: they’re not all like that anymore.
The meticulously dressed and preened working girls we see depicted in media don’t seem to exist in the the great outdoors. A building management executive informed us that “most women don’t dress up for the commute to work. They keep their heels in a bag or under their desk and become beautiful at the office.” These ladies know their days are going to be action packed, and they would rather be comfortable in flats than be concerned about appearing a bit ragged. One woman said she didn’t even have time to smooth out her hair, and had plans to do so at the office. Another, a lawyer, who we caught on a mid-morning coffee run, had her pearl earrings in place and her hair done. As for the men, the majority are in suits (some better fitting than others), and we encountered the most dapper accountant (seriously), who debunked the myth of the drab number cruncher. He looked positively sharp in a velvet bow tie, fitted suit and a polka dot pocket square—it isn’t a special occasion outfit either, because he dresses like this all the time. We even spotted some international businessmen—one sporting a backpack and wayfarers, and another wearing a finely knotted scarf (oddly, both were reading the Toronto Sun). Among the ever-changing world of the Financial District, there’s also a community we discovered that exists outside the gauntlet of high towers. We met a glamorous neighbourhood retiree who cuts through Oscar Peterson Place on her way to a morning yoga class every week; an executive who makes the concrete jungle his pre-meeting running room; and bike couriers who race through the streets alongside bros on Bixis.