Hardly your average hotel souvenir shop, the Drake General is where Canadian kitsch meets Queen West cool. Lining its smartly curated shelves are reams of wrapping paper printed with antique maps of the Great Lakes, vibrant wool throws from Prince Edward Island, apothecary products named for seminal years in Canadian history and the softest imaginable striped tees by in-house label Shared Beloved Basics. A favorite find among all the chic miscellany: Toronto brunch maps hand-illustrated (and annotated—"coziest booths!", "yummy latkes!") by a bacon-enamored local artist, each enclosed with a checklist for keeping track of brunch conquests.

Toronto is a vintage-lover's wonderland, but even shoppers who possess no fondness for foraging will want to peek inside this tiny trove of antique jewelry, leather accessories and other nostalgic baubles. Highlights include patinaed Edwardian lockets and the wall of boots in worn-to-perfection shades of cognac and caramel, priced at twenty-five dollars a pair. Original Victorian display cases house the well-edited jewelry collections, adding to the air of sepia-toned romance.

Kasha Billobram's effortless street style is on display inside her laid-back Queen West boutique, where she stocks elevated basics in urban neutrals and architecture-inspired jewelry by promising local makers. Look for hammered brass bracelets from Michelle Ross and layerable cotton cord necklaces by Rune.

This petite boutique's curators are also the designers behind Toronto's twenty-year-old indie label Mercy Studio. They've spent their careers cultivating relationships with independent textile mills around the globe, so it's no surprise that Gaspard's racks are lined with quality fabrics from interesting places. Most of the collections carried here—by small designers from Japan, Italy, Finland and Belgium—can't be found anywhere else in Canada. There are digitally printed silk dresses, convertible fringed Oxford booties and whimsical, patterned apparel featuring toucans and cacti, all of which look right at home alongside the shop's avant-garde parent-label.

This menswear outfitter-cum-espresso bar supplies dapper gents with heritage utility boots, artisanal beard oil, masculine Miansai cuffs and Shinola watches. Bestsellers include old-school workman's Henleys by Vancouver-based brand Homespun and surf trunks designed on Toronto's own beaches.

Master tailor Sydney Mamane got his start as a wardrobe technician in Toronto's film industry. Before opening up shop on Queen West, he built a reputation providing bespoke denim and suiting services out of a private studio. Though he still offers appointment-only, made-to-measure tailoring, Sydney launched his own line, United Stock Dry Goods, in order to make his designs more accessible. At the boutique, which is as minimalist and clean as his silhouettes, United jeans hang alongside hand-picked Italian and Japanese labels.

This neighborhood bookseller (known for imaginative window displays) champions small press titles, sponsors literacy programs at local schools and hosts a weekly story-time for young readers. Spend an afternoon leafing through design magazines in its chandeliered foyer, and you're likely to leave campaigning for the preservation of print.