In a city rife with indie fashion pop-ups (we're looking at you, Roden Gray) and shopping malls, you'd be forgiven for thinking the old-school general store had gone the way of pleated pants. But Hill's has been a fixture here since 1914, first as a dry-goods shop hawking fabric and yarn among other assorted staples, then focusing on men's and women's clothing. "Back then, the market was 90 percent functional clothing, and 10 percent fashion," says Ross Hill, the third-generation family member to take up the sartorial mantle. The vintage-brick shop's continued success comes from skewing more heavily toward on-trend fashion now – womenswear coup de force Aritzia was originally run from the basement of Hill's, courtesy of brother Brian – but this is still the place to go for classic labels like Levis Made & Crafted, Barbour and Rag & Bone. It's an ethos that tempers high style with the ageless quality that made it an institution in the first place.
2125 W. 41st Ave., 604-266-9177, hillsofkerrisdale.com
Manufactured in the last remaining toothpick mill in North America, Daneson's small-batch Bourbon No. 22 toothpicks are imbued with a subtle boozy flavour (also available in lemon, birch and single malt).
The interior of this full-service menswear boutique is open-concept for two reasons: to highlight the distressed 1912 brick of the converted warehouse, and to let you visualize your year's wardrobe at one glance – from summery AMI woven-cotton Henleys showcased in the front to cozy cashmere-and-silk-blend Corneliani swatches in the back. Somewhere in between, you'll be greeted by veteran suit-salesmen Brad Kahler and Chad Helm, a pipe fitter turned model whose years on Milan runways taught him a few things about Italian garments. "Don't judge me," he says, sniffing a Tino Cosma pocket square with a burnt odour, "but high-end fabrics all have interesting smells." When Chad and Brad aren't on the floor, they're scouring fashion capitals for new lines like Ovadia & Sons, or buying Luigi Bianchi Mantova's latest.
10125 104th St. N.W., 780-425-4344, thehelmclothing.com
The appeal of precious stone and chain cufflinks by homegrown designer Michael Kaye – now a fixture of New York haute couture – is all in the wrist.
Espy's unassuming sign offers few clues as to what's inside the revitalized warehouse: more than 3,000 square feet of fashion for men and women. Owner and stylist Megan Szanik has a well-edited selection from international as well as local designers, specializing in the difficult-to-fit. "I'll choose a more generous cut of shirt from Cafébleu for my plus-size guys, while Denmark's Matinique line of shirts and pants offers a more slim fit," she explains. Waistcoats by Ted Baker, Montreal's Kuwalla Tees and hard-to-find socks for boys by Marcoliani round out the mix. Men can also outfit themselves with a made-to-measure look, including suiting and shirts with choice of cuff, collar or stitching. Szanik carries innovative womenswear, too: prints from Barcelona's Desigual, vintage-inspired dresses by Stop Staring and leathers by local designer Bano eeMee.
1009 9th Ave. S.E., 403-457-3779, espyexperience.com
The key to hitting best-dressed lists is knowing how to put everything together, and Tasha Myslicki, Espy's menswear manager, can help with a closet intervention. She'll toss, tailor and recommend essentials for a timeless look.
Put Your Best Foot Forward
Feat of engineering or soulful work of art? With quality craftsmanship and luxurious leathers, bespoke shoes from Leatherfoot in Toronto or Jon Gray in rural Nova Scotia are both. Consider those calfskin oxfords or kangaroo brogues an investment that will keep you on your toes.
Owner Sydney Mamane made bespoke jeans out of a small studio before opening Sydney's at his current Queen Street location in downtown Toronto. Nearly a decade has passed since he launched the retail store, and his concept has grown with the neighbourhood. Racks of ready-to-wear suits, colourful shirts and casual shorts – some of them from United Dry Stock Goods, the modern and minimalist label he co-founded – hang above the gleaming church pews that hold tidy rows of the denim pieces that still anchor the shop. With his slate-grey glasses and yellow tailor's tape, Mamane is a true haberdasher, creating made-to-measure pieces at the rate of about one a day in a style that combines traditional English and Italian suiting with dashes of the Edwardian, Jazz Age and Mad Men eras.
682 Queen St. W., 416-603-3369, shopsydneys.com
The glass curio cabinet beside the checkout displays impulse-buy items like a canvas Billykirk travel bag and jars of Imperial Barber Grade Products Field Shave Soap.
Luxury e-tailer SSENSE welcomes around two million visitors a month, but you'll have plenty of space to shop in its two-storey, bricks-and-mortar boutique. Flanked by Old Montreal's galleries and French restaurants, the industrial-chic locale is as sleek as the lines it carries, including Chloé, Balmain and Givenchy. Stop by for a smart cardigan or a little black dress and you might just leave with a deconstructed leather jacket. You'll also find high-end, collectible streetwear from the bad boys of fashion – look for Rick Owens mesh baseball caps and Maison Martin Margiela high-tops. Want to shop like a local? Pick up a passport holder or a weekender bag from much-loved Montreal label Want Les Essentiels de la Vie.
90, rue Saint-Paul O., 514-289-1906, ssense.com
If you like to browse online but buy IRL (in real life), SSENSE can have items shipped straight to the shop – like that Junya Watanabe reversible canvas jacket – with no obligation to purchase.
It may sound like the lead-in to a joke – three lawyers and a physiotherapist walk into a department store – but Candace Thomas, Kath Perry, Deanne MacLeod and Lisa Gallivan mean business. A few months after a cosmopolitan-fuelled chat where they all confessed to dreaming of owning a store, a Spring Garden Road institution (first opened in 1919 as Mills Brothers) came up for sale, and they jumped at the chance to purchase it. Now open in a new location with 10,000 square feet spread over two retail spaces and featuring a number of lines not available elsewhere in Atlantic Canada, like Judith & Charles and Chanel Beauty, along with Kate Spade handbags, accessories and shoes, Mills is set to become the shopping destination for womenswear east of Montreal. So keep your eyes peeled for return client Jeanne Beker, who spends a lot of time on the Nova Scotia shore.
5640 Spring Garden Rd., 902-429-6111, millshalifax.com
Carrying on the tradition of making alterations to new outfits at no extra charge, Mills kept on the seasoned seamstress from the previous store.
It's in the Jeans
Finding the perfect pair of jeans can be a frustrating experience, so for expert assistance and an unmatched selection with a nod to Canadian content, visit Dutil's Vancouver flagship store, in Gastown, or Leo Boutique in Calgary and Vancouver. Both feature Montreal brand Naked & Famous, which combines old-school technique, modern fit and cutting-edge fabric.