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It's awful, I love it

Ill-fitting pants, oversized tops and chunky sneakers: Jeremy Freed reports on the improbable rise of ugly fashion

Toronto boutique Soop Soop blends old and new in unexpected ways with clothing that is both decidedly cheesy and at the height of cool.

With its mix of sketchy sports bars, laundromats and hipster speakeasies selling $14 cocktails, Dundas West is the epicentre of Toronto's gentrification. It retains some of the feel of the immigrants from Italy and Portugal who settled here 50 years ago, but that is rapidly giving way to the downtown's signature mix of hip young creatives and urban professional families with million-dollar starter homes.

Soop Soop, a store that sells clothes and magazines to the neighbourhood's newer, artsier residents, blends old and new in unexpected ways. With its bright fluorescent lighting, grey carpet, vertical blinds and white plywood pegboards, Soop Soop has the feel of an early nineties Radio Shack. Indeed, if not for the shelves displaying high-concept fashion magazines, such as Toilet Paper, Fat and Polanski, you might never guess you were in one of the city's most avant-garde boutiques. The clothes themselves are no less confusing.

"We just generally try to approach things with a sense of humour," co-owner Christina Pretti says. "We'd always rather something feel cheesy or silly over cool."

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Soop Soop's baggy pants and ruched pink silk shirts are ugly – and that's precisely the point.

Such is the strange nature of the present moment in fashion that the clothes Soop Soop sells are both decidedly cheesy and the height of cool: wide denim cargo jeans, baggy mock-neck long-sleeved Ts and ruched pink silk skirts that would have slayed at a prom in 1988. They're also, by any standard definition, quite ugly. And that's precisely the point.

"I'm one of the proponents of ugly fashion," says Tanya White, who teaches avant garde and conceptual design at Ryerson University's fashion school. "I think it's interesting if you can look at someone and think, 'Are they really cool or is that just an awful outfit?' "

Pretti and White are not alone in this fascination. In recent years, a handful of emerging designers have made names for themselves with just this sort of rejection of traditional aesthetic. Vetements, launched in 2014 by Louis Vuitton and Maison Martin Margiela alumnus Demna Gvasalia, drew praise for its comically oversized sleeves, gender-fluid silhouettes and hacked-apart DIY construction. Similarly, brands such as Off-White, Hood By Air and Gosha Rubchinskiy have pushed boundaries with off-kilter blends of high-fashion, streetwear and thrift-store sportswear chic.

Bigger brands are getting ugly, too. Balenciaga (now helmed by Vetements' Gvasalia) caused a stir with the release of the Triple S, a chunky $900 "It" sneaker that looks like something salvaged from a Kmart fire sale in 1992. Kanye West's Yeezy brand subsequently dropped a similarly ungainly pair of kicks, the new Desert Rat 500, to an immediate buying frenzy, and Gucci is doing brisk business in its new range of $1,500 fanny packs (including one in hot pink). When Christopher Kane sent a collection of crystal-embellished Crocs down the runway for Summer, 2017, it became clear that the true potential of ugliness in fashion had yet to be fully glimpsed.

Nostalgia, ever fertile ground for designers, can account for some of this trend's appeal – as can the allure of comfortable shoes – but not all of it. There's something about ugly fashion that seems more insidious: at best a challenge to those who want to be seen wearing the latest hot designer, at worst a joke at their expense.

Ryerson's Tanya White believes it's a reaction to both the speed and ubiquity of fashion – it simply has nowhere else to go. "We've come to a point where the cycles are moving so quickly that it's difficult to find new aesthetics and new ideas," she says. "Basically, designers are almost going to this ridiculous place, because not everybody will wear it and not everybody will know what to do with it."

Nostalgia can account for some of the appeal of ugly clothing.

The longer ugly fashion remains popular among those who do know what to do with it, however, the faster it will spread.

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"Five years ago we would have never seen someone like Rihanna or Kim Kardashian wanting to be a part of this," White says. "Celebrities are desperately trying to push the boundaries. Some trends will not catch fire, but some trends definitely will. It will take the right style blogger or celebrity to wear those Crocs, and sure enough … "

On Dundas West, a man in a baggy New England Patriots jacket, rumpled wide-leg jeans and beat-up white running shoes ambles down the sidewalk. It looks for a moment as though he's headed for Soop Soop, possibly to pick up the latest copy of Luncheon magazine or browse the selection of oversized airbrushed T-shirts by Gauntlett Cheng. Instead, he keeps on strolling down the block, toward a crowd of similarly dressed men smoking outside the Portuguese sports bar on the corner. Is he really cool or is that just an awful outfit? It could be that both things are true.

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