This post was most recently updated on December 8th, 2014

Just a quick walk DT is all it takes to spot a handful of trendy Toronto street style women’s boots! From rugged & boyish classic Timberlands, to buckled, quilted & Chelsea styles with girly prints, it’s easy to see, via its shoes, why TO is one of the Canada’s most fashionable cities. See some of my preferred boot trends for Fall 2014, below.

  • On-Trend, Buckled Black Ankle Boots

Toronto Street Style Women's boots

Buckles & chunky heels anyone? The perfect leather boot this season has a block heel & metallic hardware. These Sam Edelman ankle boots with double buckles in a great black leather are from Capezio.

  • Work Boots

Toronto street style timberland boots

I spotted a diversity of Fall boots in the city in the Annex/Bloor St area recently. Work boots or a play on them is big for Fall. But in particular, classic Tims are getting serious time in the spotlight, even more so this year, with Rihanna sporting these rugged boots in many street style looks. Rocking them with denim & colorful faux-fur turns gives them a feminine, unexpected edge! I spotted these on Bloor St styled with heathered charcoal sweats in a masculine, sporty fashion. A ton of retailers in TO carry these, including Canadian online retailer Shoeme.ca.

  • Leopard Print

Toronto Street Style Women's rain boots

If you follow ShoeTease on Instagram, these will be familiar to you; I absolutely adore these leopard print J.Crew ankle rain boots. The Chelsea boot detailing & the contrasting semi-opaque heels & pull tabs complete what I believe is the perfect weather-proof design. I actually spotted these in the neighborhood grocery store parking lot. I hope I didn’t weird out the nice lady too much by my enthusiasm for her shoes!

  • The New Chelsea Boot

toronto street style womens boots4

I couldn’t help myself: I had to include another Chelsea boot. These ones are from Kate Spade & they’re a really good looking rain boot (which you can hardly tell when looking at them!). The gold detailing around the outsole is as slick as the original shape of the elastic insert.

  • Textured Moto Boot

toronto street style womens boots 1

The updated moto boots this Fall incorporates quilting. Actually, quilted materials are a huge trend from furniture to clothing to shoes. All within the design sphere, really. I just bought a similar water proof, insulated pair from London Fog almost identical to these from The Bay. These are the perfect transitional Fall to Winter boots: protective enough to stomp in a slush puddle or two!

Check out more Toronto shoes spotted on the streets, including these men’s brogues with colorful socks & bright New Balance sneakers.

xo Cristina M.

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