Best women's boots for fall 2023: Chelsea, ankle, combat & more

When it comes to fall in Canada, investing in a good pair of boots is a seasonal pre-requisite. Fall boots are not only tasked with providing warmth and stability, but the right shoe can change the entire vibe of an outfit.

The silver lining of living in a boot-mandatory climate is that you can invest in a few pairs without feeling guilty. You, of course, need your inside boots, your outside boots, your going-out boots, and at least a few pairs that can hold up to Mother Nature's wrath.

While we can safely assume you have at least a few of the former in your closet, chances are you could use a new pair (or three). Therefore, we've gathered 27 pairs of exceptionally chic boots for your fall 2023 wardrobe, including the:

Best Black Boots

Best Chelsea Boots

Best Heeled Boots

Best Waterproof Boots

Best Knee-High Boots

Best Ankle Boots

Best Western Boots

Best Combat Boots

Best Sock Boots

No matter what boot you have in mind, we're confident you'll find something you like. Read on to shop the edit.

The details: UGG's iconic booties have been reimagined for fall/winter 2023/24 in a minimalist short design. The incredibly cozy shoes feature genuine suede uppers and warm and comfy sheepskin lining.

Available in: Black and fawn brown. Women's sizes 6 to 10.

$185 at Simons

The details: Introducing your new favourite "I got this" shoe. These classically cool knee-high Sylvia Boots have a leather upper and three-inch heel.

Available in: Black and gold leather. Women's sizes 5 to 11.

$200 at Anthropologie

The details: Get ready for an onslaught of "where did you get those?" questions when you don these seriously cool ankle-high buffed leather Chelsea boots from Toga Pulla.

Available in: Black leather. Women's sizes 35 to 41.

$490 at SSENSE

The details: When the temperature starts to tank, you'll reach for these Leonore Chelsea Docs. The cold weather-friendly boots are lined with cozy faux fur and have a treaded rubber sole.

Available in: Black leather. Women's sizes 5 to 11.

$235 at SSENSE

The details: These timeless Chelsea boots from Maguire, a Canadian label at Simons, feature a trendy square toe with genuine leather uppers and lining.

Available in: Assorted white, brown and black. Women's sizes 35 to 42.

$260 at Simons

The details: These snake-effect Chelsea boots from Ganni are the cool-girl shoes you've been searching for. They're made of 100 per cent leather and feature a stacked heel and square toe.

Available in: Brown leather. Women's sizes 35 to 41.

$298 $595 at The Outnet

The details: Aren't these just darling? With their gold embellishments, Lola Cruz's Gorges Boots are the extra "oomph" you're outfit called for.

Available in: Black leather. Women's sizes 36 to 41.

$290 at Anthropologie

The details: A steal at just $56, these H&M heeled Chelsea boots will become one of your most-worn shoes this fall (and beyond).

Available in: Black. Women's sizes 4 to 11.

$56 $70 at H&M

The details: It's been a long year, you deserve a new pair of shoes. Specifically, these eye-catching croc ankle boots from Silent D.

Available in: Seven colours, including red and black. Women's sizes standard and wide, 35 to 42.

$140 at Anthropologie

The details: Not only are these Blundstone Chelsea Boots incredibly comfortable and safe for Canadian weather, but they've earned a royal seal of approval from Princess Kate herself.

Available in: Black leather. Women's sizes 6 to 10.

$265 at Simons

The details: Everlane's The Rain Boot is the perfect option for people who don't like the look of rain boots. Their versatile ankle height plays well with jeans and the shoe's slip-resistant tread helps avoid slippery sidewalk pitfalls.

Available in: Six colours, including black and sage green. Women's sizes 5 to 11.

$135 at Everlane

The details: Another royal-approved shoe on the list, these tall classic rain boots from Hunter pack an extra punch with a bold tri-color logo on the backstrap.

Available in: Three colours. Women's sizes 6 to 11.

$252 at Free People

The details: If you're looking to invest in your footwear collection this fall, may we suggest starting with Stuart Weitzman's Keelan City 100 per cent leather knee-high boots?

Available in: Black. Women's sizes 35.5 to 42.5.

$452 $694 at The Outnet

The details: These leather riding boots offer equestrian-inspired details and feature Aldo's flex technology for added comfort — aka, they'll be a sure-fire hit at the pumpkin patch.

Available in: Black and brown leather. Women's sizes 6.5 to 10.

$220 at Aldo

The details: Anthropologie reviewers can't get enough of these "gorgeous suede boots." According to one shopper, they're "very comfortable" and a "great fall boot to wear with skirts or dresses."

Available in: Rose pink, black and sand. Women's sizes standard and wide, 36 to 42.

$178 at Anthropologie

The details: These sleek BOSS by HUGO BOSS suede ankle boots are timelessly elegant and ready for every party, date and "just because" event on your calendar.

Available in: Black suede. Women's sizes 36 to 41.

$328 at Simons

The details: We can't decided which outfit we want to pair these leather ankle boots with first: a boho maxi dress or cuffed jeans and a tee.

Available in: Brown leather. Women's sizes 5 to 10.

$160 at Mango

The details: You can't go wrong with a pair of Dr. Martens ankle boots. The street-style favourite is fashioned with leather and dual gores for a little extra stretch.

Available in: White and black leather. Women's sizes 5 to 11.

$170 at DSW

The details: This two-toned boot is the thing of honky tonk dreams. The Dolce Vita booties have a leather upper, dual stretch panels and a solid block heel.

Available in: Black/white. Women's sizes 7 to 10.

$110 $200 at DSW

The details: But for real, how good are these? These oh-so-cool western-inspired boots from Jeffrey Campbell feature classic embroidered details in luxe leather with a pointed toe and block heel.

Available in: 11 colours, including lilac metallic, gold and silver. Women's sizes 6 to 11.

$367 at Free People

The details: Giddy up, cowgirl. These trendy Western-style leather boots feature Aldo's Pillow Walk soles for comfort and a block heel.

Available in: Black leather. Women's 5 to 11.

$198 at Aldo

The details: These incredibly cool Dr. Martens are perfect for anyone bored of black boots. With thousands of "loves" from Free People shoppers, reviewers say they're "gorgeous" for fall.

Available in: Black leather. Women's sizes 5 to 11.

$272 at Free People

The details: We've never seen combat boots like these before. These surprisingly glam stomper boots feature pretty embellished crystal laces and a rubber sole.

Available in: Black leather. Women's sizes 5 to 11.

$218 at Anthropologie

The details: These trusty Docs feature the brand's iconic rubber air-cushioned sole and yellow stitching.

Available in: Six colours, including fuchsia and white. Women's sizes 5 to 13.

$231 at Free People

The details: Everlane's iconic The Glove Boot offers the perfect amount of stretch for all-day comfort. The fit-like-a-glove boots have racked up nearly 1,400 reviews from shoppers and an average 4.7-star rating.

Available in: Black, bone white and dark brown. Women's sizes 5 to 11.

$238 at Everlane

The details: These perforated ankle booties have an architectural block heel and a square-toe design. With an average 4.9-star rating, reviewers call them "comfy and stylish" and "good quality."

Available in: 11 colours, including black, eggplant and grey. Women's sizes 5 to 11.

$139 at Vivaia

The details: These water-repellent knee-high sock boots are the cozy going out shoes you've always dreamt of.

Available in: Five colours, including black, chocolate and grey. Women's sizes 5 to 11.

$189 at Vivaia

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