Street Style: 19 looks at the women of Rosedale

Words by Kevin Naulls | Photography by Jenna Marie Wakani

Welcome to The Goods’ brand spankin’ new street style segment, where we ditch hackneyed questions like “How would you describe your style?” and infuriatingly meaningless answers like “rockabilly-meets-schoolmarm-meets-zoologist-chic.” Instead, every second Friday, we’ll be deconstructing the stereotypes that have come to characterize a Toronto neighbourhood, shooting subjects in the urban wild to determine whether the prevailing style myths are actually bona fide truths. This week, we look at the women of Rosedale, who have traditionally been viewed as the Dowager Countesses of Toronto—complete with entitled, upturned chins, Whole Foods status totes, “it” handbags, tennis skirts and a variety of Ugg-like footwear (when they just can’t bear to wear their Louboutins). But is the Rosedale woman the status-hungry, label-wearing matron she’s presumed to be? The truth is so much more interesting than that.

Among the cherry blossom trees in Ramsden Park—donated to the community by Mitsubishi in 1985—we encountered a comfortably dressed activist carrying a scarlet cross-body bag (to hold her posters advocating park beautification). It’s a getting-your-hands-dirty uniform we certainly didn’t expect for a neighbourhood that houses some of Toronto’s wealthiest families (she herself has been an active member of the community for many years). Just off Macpherson Avenue, near theatre director Stephen Katz’s former residence (a pig-farm-cum-apartment, if you can believe it), we encountered model-esque shop girls and prep school teens who seem to have doffed their off-duty Birkenstocks and woolen socks for something more refined (or they channelled the style code of a Queen West wanderer). But some habits die hard, because not everyone wants to play the eccentric artist, or the “not-your-average Rosedale mom.” Some still committed to the casual-meets-sophisticated uniform of a classic trench, running shoes and a collection of organic groceries. One wealthy man remarked that “rip-off road,” or the stretch of Yonge just off Price Street, featuring grocer Harvest Wagon and butcher Oliffe, is where the typical Rosedale nouveau-riche is most often spotted, but we were hard-pressed to find more than a handful of examples of the well-worn archetype. Perhaps our subject is out batting balls at the members-only Toronto Lawn Tennis Club between private shopping trips—but we’re convinced she’s less thorny than the city sometimes imagines, and less showy than the wannabes who wander the streets, drinking their lattes, aspiring to live this largely imagined life.

Click here to see 19 women of Rosedale »