Toronto’s 20 best street style looks from 2016

By Jean Grant | January 1, 2017

By Jean Grant | 01/01/2017

In 2016—a year in which pantsuits, statement T-shirts and topless selfies dominated the fashion discussion—Toronto’s best style wasn’t so much about what pedestrians wore, but how they wore it. Whether they were hitting the pool in a summer heatwave, hiding out in the PATH in the dead of January or repping their favourite artist, Torontonians wore winning outfits with serious swagger and attitude, regardless of designer cred or price tag. Here, the best looks of the year:

Amanda Prow

Spotted in Yorkville
A shapeless chambray dress thrown on over cropped pants adds some edge to relaxed winter layers (and let’s be honest: that hair is a statement accessory on its own).

Luke Pelosi

Spotted in the PATH
With distressed jeans and a tailored navy blazer, this finance guy has mastered “Bay Street Casual.”

Harby Fayehun

Spotted at Toronto Men’s Fashion Week
When worn properly—and paired with your best blue-steel stare—a chunky knit scarf can elevate any winter outfit.

Diane Clemons

Spotted at The Room
It takes hardcore fashion dedication to sport towering platform stilettos on a shopping excursion.

Justinei Iaboni

Spotted at Toronto Fashion Week
How to flawlessly flaunt icy winter pastels (and breathe new life into your old ballet tights), courtesy of one of Toronto’s top fashion bloggers.

Josh Alvernia

Spotted at Sherway Gardens
This guy proved edgy ’70s style has even penetrated Toronto’s suburban malls.

Shuko Stopyra

Spotted at George Brown’s downtown campus
Despite 2016 being generally crappy, you can’t help but smile at this woman’s playful outfit, complete with a hula hoop, leopard-print socks and eyeball drop earrings.

Bismark Adomako

Spotted at Toronto Fashion Week
This is one impeccable suit, with a cheeky bright-red cherry of a chapeau on top.

Jeremy Burns

Spotted at the Rogers Centre
This guy manages to go all-out in the fan department without sacrificing any style.

Agatha Bieniek

Spotted at the ROM
This artsy museum-goer has a distinctly Parisian vibe.

Carl Woo

Spotted at the AGO
And this art gallery look features a shirt that could very well be on display.
queen's plate

Spotted at the Queen’s Plate
We commend this Queen’s Plate attendee for her fresh, modern take on race-watching attire.

Zahra Haneef

Spotted at Toronto Fashion Week
This woman pulled off the year’s boldest beauty trend: glittery brows.

McKenzie Fraser

Spotted in Leslieville
As far as pint-sized style goes, this girl—who “only wears dresses”—kills it in a ballerina-inspired ensemble.

Najma Eno

Spotted at Alexandra Park pool
This pool-goer makes shades of pink look more badass than girly.

Scott Osborne

Spotted outside the Beyoncé concert
During the city’s Lemonade frenzy, this guy took DIY to the extreme.

Mackenzie Loop

Spotted at the CNE
A bandana around the neck gives this Aritzia devotee’s outfit a flash of carnival spirit.

Evie Begy

Spotted at Toronto Fashion Week
Here, a show-goer demonstrates how to sport playful emojis while still looking supremely sophisticated.

Katarina Poletto

Spotted at Spadina Museum
This Gatsby getup is a direct line back to the 1920s—but take away the gloves and parasol and the dress is definitely 2016 cocktail party appropriate.