FOR WOMEN
Contemporary
(Image shows from left clockwise: Narwhal, Jonathan and Olivia, Chasse Gardee, The Drake General Store)

Name: Jonathan and Olivia
Location: 49 Ossington
The Deal: Opened in August 2008, J+O quickly became Toronto’s hippest boutique. Since then, the owner has continued to take on more well-designed brands, married Surface 2 Air co-founder Nic Jones, and opened up the first in-store Topshop boutique in Canada, solidifying J+O as a must-shop destination without losing the unpretentious, well-curated vibe of a small boutique.
What You’ll Find: Cult-favorite brands like Surface 2 Air, Acne, Rick Owens’ Drkshdw and more alongside Rag & Bone, Isabel Marant and lesser-known International brands like Our Legacy and Whyred. Not to be missed is the store’s Topshop boutique, an installation stocked with only the best pieces from Topshop’s collection, including Kate Moss for Topshop and Unique.
www.jonathanandolivia.com

Name: Chasse Gardee
Location: 1084 Queen Street West
The Deal: Literally meaning “private hunting ground,” Chasse Gardee is a sliver of a shoe store that makes up for what it lacks in space with style and personality. The owners are friends with nearly every other retailer on the block and they even hold a pay-what-you-can yoga class in-store.
What You’ll Find: A stylish selection of shoes from indie designers SuYoon, A Detacher, Finsk and YMC and more mainstream labels like Jeffery Campbell. Go for the shoes, but don’t be surprised if a few of the well-edited selection of locally designed jewelry and ready-to-wear bags catch your eye too.
www.chassegardee.com

Name: Narwhal
Location: 8 Price Street
The Deal: Carrying only the best from international and local designers and done up in Persian rugs and vintage furniture The Narwhal might just make the residential area it presides in a shopping destination in it’s own right.
What You’ll Find: Labels like Rachel Comey, Fjallraven, Helmut Lang happily coexist alongside homegrown labels like Chloe Comme Parris, Erin Kleinburg and curated oddities like the hilarious Mean Cards and 7-foot narwhal tusk.

Vintage
(image shows from left, clockwise: 69 Vintage, Courage my Love, I Miss You Vintage accessories, I Miss You Vintage furs)
Name: 69 Vintage
Location: 1100 Queen Street West
The Deal: It’s got a fun, quirky vibe and the sales people and owner are super friendly. They also teach vintage-inspired sewing classes and host epic, themed parties that go well past midnight.
What you’ll find: A great selection of stylish winter gear, from well-priced furs ($100-$200) to utterly warm classic cowichan sweaters ($90-$120). They also have affordable cocktail dresses, boots and quirky-cool accessories. I walked away with a gorgeous colorful scarf from South America for $20.
www.69vintage.com

Name: I Miss You Vintage
Location: 63 Ossington Avenue
The Deal: Arranged by era, I Miss You vintage is a well organized, easy-to-shop treasure trove of great pieces. Usually pretty quiet, the staff is welcoming and happy to help shoppers find that special item they’re looking for.
What you’ll find: High-end vintage without the astronomical price tag. I Miss You stocks vintage Missoni, Chanel, YSL and Lanvin but prices them really well–Those Chanel pumps (pictured) were only $60! You can also nab more contemporary, gently used pieces from labels like Dries Van Noten, Prada and Comme des Garcons at guilt-free prices.

Name: Courage My Love
Location: 14 Kensington
The Deal: The first vintage store to open in Kensington Market (a hippie outpost and vintage), Courage My Love is a requisite stop when visiting the strip. Like all Kensington shops, the vintage store is run out of a converted old Victorian townhouse, which the owners have painted blue and decked out in Buddhist prayer flags.
What You’ll Find: Organization isn’t their strong suit, but the piles of vintage sunglasses, gloves and jewelry from all over the world is well worth a good rummage. Cat eye glasses from the 60s ($40) are among the favored go-to buys, while a huge selection of vintage dresses and lingerie at low prices are the perfect hunting grounds for discerning shoppers. Courage my Love also stocks thousands (and we mean thousands) of vintage and contemporary beads and buttons for the stylish DIY-er.

High-End
(Image shows from left: Holt Renfrew, The Room at the Bay)
Name: Holt Renfrew
Location: 50 Bloor Street West
The Deal: Long heralded as the Barneys of the North, Holts is an essential stop for any shopping enthusiast. Located in the heart of Yorkville (Toronto’s answer to 5th avenue), Holts has all the trappings of a major department store: four stories packed with high-end designer labels, contemporary lines, handbags and shoes and decorated in the obligatory bright-lights-beige-carpet fashion.
What You’ll Find: Holts has all the goodies: From Chanel, YSL and Gucci (which all run boutique-esque departments within the store) to more affordable lines like Alexander Wang, Richard Chai LOVE, Vince, Theory and more. They also boast hundreds of shoes, sunnies, handbags, two great cafes and fantastic people watching.
www.holtrenfrew.com

Name: The Room at the Bay
Location: 176 Yonge Street
The Deal: After a recent facelift courtesy of famed interior designer Yabu Pushelberg, The Room is poised to usurp Holts’ monopoly on high-end retail. Its airy and futuristic décor is the perfect setting to showcase the huge selection of designer duds that will have any shopaholic’s mouth watering.
What You’ll Find: All the usual suspects (Prada, Chanel, 3.1 Philip Lim) alongside up-and-coming designers, particularly, a fresh crop of British talent (Charlotte Olympia, Giles Deacon, Mark Fast), which the department store recently honored with a God Save the Queen gala and all-out shopping extravaganza.
www2.thebay.com