Street Style: the 20 best looks from 2015

2015 was a big year for Toronto style: Drake made turtleneck sweaters cool again, The Weeknd’s hairdo inspired celeb Halloween costumes and we even got our own Nike sneaker. But it was the city’s regular citizens—spotted everywhere from the Beach to Parkdale, OVO Fest to the MMVAs and OCAD to U of T—who gave our fashion game the biggest boost. Here, our 20 favourite outfits from the year, including the impossibly chic, refreshingly simple and outrageously inventive.

Name: Paul Mason
Spotted: Outside Toronto Men’s Fashion Week
Only Fashion Santa (at his day job, of course) can make a simple black-on-black combo look this stylish.

Name: Bianca Venerayan
Spotted: Woodbine racetrack, for the Queen’s Plate
A Toronto blogger uses DIY flair to give the typical horse racing getup (i.e.: frills, florals and over-the-top headpieces) a mod update.

Name: Shirley Walker
Spotted: Woodbine racetrack, for the Queen’s Plate
This 88-year-old attendee shows that sticking to a classic look (complete with an over-the-top headpiece) can be equally striking.

Name: J.J. Wilson
Spotted: David Pecaut Square
The Kit and Ace founder proves that luxe basics can still cut it at Fashion Week.

Name: Nick Capretta
Spotted: OCAD’s Queen West campus
We predict the “urban Amish” look will be big for 2016.

Name: Catriona Smart
Spotted: David Pecaut Square
Monochromatic looks were everywhere this year. This blogger used multiple shades of grey to keep things interesting.

Name: Pierre Thomson
Spotted: Kensington Market
There’s something about this pastor’s perfectly autumnal outfit that makes us want to snuggle up with a chai latte and wool blanket.

Names: Matt and Everling Carr
Spotted: Dundas West
The year’s coolest accessory: a super-cute kid.

Name: Sabrina De Luca
Spotted: Kensington Market
Here, a retro camera is the ideal complement to a laid-back weekend outfit.

Name: Alyssa Goodman
Spotted: Parkdale
This Parkdale resident effortlessly pulls off a few of the year’s top trends: culottes, neckties and John Lennon–inspired shades.

Name: Marcel Sokalski
Spotted: David Pecaut Square
Here’s a perfectly executed ode to the 1970s.

Name: Eliza Grossman
Spotted: David Pecaut Square
How fashion editors rock the Canadian tuxedo: under furry vests and with coordinating accessories.

Name: McCair Tulloch
Spotted: U of T’s campus
This philosophy student’s style game deserves an A+.

Name: Elena Gendunova
Spotted: Kensington Market
Behold: the trendiest nine-year-old we’ve ever seen.

Name: Michael Howard
Spotted: Nathan Phillips Square
This guy gets points for staying stylish in minus-30-degree temperatures.

Name: Olivia Lemieux
Spotted: Ashbridge’s Bay
While here, a student keeps it breezy in the scorching sun.

Name: Judith Bradley
Spotted: Kensington Market
The 71-year-old model shows us that true style has no age limit.

Name: David Sanchez
Spotted: Outside Fashion Art Toronto (FAT)
Matching the colour of your shades to your shoes takes serious dedication.

Name: Catherine Linh
Spotted: Union Station’s holiday market
We love the contrast between this traveller’s chunky scarf and her delicate metallic bag.

Name: Porshia Tomlin
Spotted: OVO Fest
Another lesson in mixing and matching done right: a Bob Marley tee paired with a preppy midi skirt.