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It’s peak boot weather, and if you’re looking to refresh your wardrobe with a new pair this fall, there are plenty of interesting styles to try at all price points.

A good place to start is thinking about where you’ll wear them. Are they mostly for the office? What does your commute look like? You might need a tread with grip if they will be exposed to some degree of rain or snow, for example, says Kalie Johnston, director of product design at Edmonton-based footwear brand Poppy Barley.

Boots are typically “a long-term purchase, something that you want to stay in your wardrobe for several years,” says Johnston. She suggests considering how well a pair will fit into your existing wardrobe, but also if they are adding something new. Consider “what are those really special details that you’re noticing,” says Johnston. “Is the heel really interesting?…Is the toe shape something that you see yourself wearing for a long time?”

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Also decide on your budget for the shoes. “Finding something that you’re going to get a lot of wear out of is a good idea, because they are so expensive,” says Brelyn Shannon, brand director at Canadian fashion and lifestyle retailer Gravitypope. She always thinks about the potential cost-per-wear of a design before making a purchase.

If longevity is a priority in your search, she also advises looking for more timeless styles and boots that can be resoled over time. If your budget allows, she says that styles lined in leather will “last you a lot longer because it’s breathable, and it’s more malleable.”

Once you’ve found a style that you like, ensure the fit is right. Some boots are only available in one foot width, while others are offered in narrow, standard/medium and wide. Calf size is another consideration if you’re buying a tall boot; one that’s too wide may slouch or fall down, and one that’s too tight around the calf will feel uncomfortable.

Even the type of socks you wear can make a difference. “If you generally just tend to wear a thinner, dressier sock, then your normal size should be fine,” says Johnston. But with thicker, heavier socks, she added that you might need to go a half-size up.

Six buys to try

In the men’s section


Astorflex Deukeflex boot



Moc toe boots are “basically a loafer in boot form,” says Shannon. “It’s a nice versatile style to dress up or down.” Made in Italy, these suede chukkas in a rich autumnal shade feature a suede upper, leather lining and a rubber crepe outsole.



Viberg Pachena Bay boot



Elevated takes on the hiking boot are trending for both men and women, says Shannon. This pair features a single-piece leather upper, a padded collar inspired by seventies climbing boots and an extra-light EVA sole. Viberg boots, designed and handcrafted in small quantities in Victoria, B.C., are made to last using time-tested techniques such as stitchdown and Goodyear welted construction.



Aldo Guthrie boot



Part of Aldo’s new capsule collection curated by basketball player Jordan Clarkson, these Western-inspired leather boots would look great with both jeans and tailored trousers. The block heel and square toe are also very of-the-moment.


In the women’s section


Sister X Soeur Lara ankle boot



Sleek, pointy-toe boots with a lower heel are in fashion and can be a versatile addition to your wardrobe, says Shannon. This made-in-Italy, leather-lined pair from Canadian brand Sister X Soeur features an anti-slip rubber heel, and is available in black as well as in a trendy hazelnut colour.



Poppy Barley Riding Boot



Equestrian boots, which appeared on the fall runways at Hermès and Burberry, are an evergreen style that is having a moment, especially in brown leather. This limited-edition pair by Poppy Barley is available in two calf widths. It’s also leather-lined and has a comfy memory foam insole.



Maguire Novelda high boot



Snakeskin print is “a great way to make a statement, but it goes with everything so you can keep it around for a long time,” says Johnston. These heeled boots by Montreal-based Maguire, available in mid-October, are made in Spain and feature a leather upper and lining.


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