In case you haven’t noticed, it’s getting chilly out there. The leaves are changing, jackets are quickly becoming more of a necessity than an accessory, and those open-toe shoes? They’ve officially made their way to the back of the closet. In other words, it’s boot season! Around this is the time of year when we dig out all the boots we own—heeled, flat, ankle, knee-high—and, of course, shop for a new pair (or two) to keep things feeling ~ fresh ~. Not only are boots a practical choice as the temps drop, but they’re also a total outfit game-changer. A great pair of boots can take an outfit from 0 to 10 in an instant. And let’s face it, no fall wardrobe is complete without a new pair of “fall-approved” boots.

We found 11 pairs of fall-approved boots to shop

All products featured in this article were independently selected by our team. By shopping through our links, we may earn a small commission at no additional cost to you. 

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The fall season is quickly approaching, and there’s no better way to step into a new season than with a pair of fresh shoes. This fall, there are so many chic shoe trends just waiting to be worn! From knee-high boots to burgundy loafers to Mary Jane ballet flats, there is no shortage of stylish options to add to your collection. If you’re ready to strut your way into fall, these shoes have you covered. 

Shop these 10 styles!

All products featured in this article were independently selected by our team. By shopping through our links, we may earn a small commission at no additional cost to you. 

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As we’re currently in the thick of winter, we are most commonly confronted with two types of weather conditions. Snow or slush. And we can always expect the “slush weather” to last well into spring (yay, us). There’s nothing worse than having cold and wet feet while out and about, which is why it’s absolutely essential to have slush-proof boots to walk through the Toronto streets in. Bonus points if they’re also cute.

Here are some of the best slush-proof boots to take you through the city

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Toronto, we’ve been greeted with our freezing rain storm of the season. If that isn’t a memo to have some winter boots on standby, we don’t know what is! Although winter doesn’t technically start until later in December, we tend to get an early glimpse here. We can probably all relate to the dread of putting away our chic fall boots for winter ones, as the practical nature of a winter boot can make them well… not so cute. But thankfully, that doesn’t always have to be the case! If you know where to look, you can find winter boots that are both practical and cute, allowing you to strut through the streets of Toronto, even during a blizzard, without sacrificing your style.

These boots are equally cute and practical!

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If there’s one good thing about the weather getting colder, it’s that we can finally wear boots again without sweating our feet off. Pulling out our fall boots and shopping for a new pair or two to add to the collection is something we look forward to as soon as September hits. As much as boots are always in style throughout the fall months, this year feels like there’s an extra emphasis on boots and shoe trends, basing outfits solely on the decided footwear. Some boot styles that are particularly trending this fall are knee highs, western styles, suede, red, and pointed-toes, but it doesn’t stop there either. If you’re looking to shop for some fall-approved boots, join us on a virtual shopping trip. 

here are 10 pairs of boots that are totally fall-approved

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Knee-high boots have been the boot of the season. Not to be confused with over-the-knee, we’re talking mid-calf to just below-the-knee style boots here. While some boots may complete an outfit, knee-high boots tend to be an outfit’s main focal point – making them so fun to style! Typically boots may be the last piece to pick out when putting an outfit together, whereas knee-highs can often be the first. Building an outfit entirely around the statement boots. We personally love them styled with a skirt, but the styling options are endless. If you’ve yet to add a pair of knee-highs to your boot collection – now is the perfect time!

Check out 10 of our favourite knee-high boots available to shop now!

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We all know that fall fashion is synonymous with cozy sweaters, camel coats, and colour palettes filled with neutrals, browns, and oranges. But when it comes to shopping for our favourite season, we’re always most excited about shopping for a trendy pair of boots that will perfectly tie a fall ensemble together. 

From fall weather-approved booties to chic cowboy boots, read on for our favourite pairs that will surely get you into the fall mood.

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If you haven’t been on social media recently, well then let me tell you, Uggs are all the rage these days. That’s right, the boot that made major waves in the fashion world in the early 2000s is back! From short to tall styles, all of the latest influencers and fashionistas are making these boots an everyday staple. If you’re looking to follow the trends but maybe switch it up a bit, there are a variety of alternatives to Uggs on the market that will not only keep your feet warm but ensure that you stay in style.

Here are awesome alternatives to Uggs to shop right now.

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If you’re in the market for a pair of winter boots that’ll keep your feet warm throughout the cold winter months, then you’ve come to the right place. With so many different styles of footwear, it can get quite overwhelming but we’ve narrowed down the top online stores to shop at to get the best winter boots. From brands offering waterproof features, double insulation, amazing sole-grip, and much more, you’re sure to find a pair that suits your lifestyle. 

Here are the top Online stores to shop at for the best winter boots.


KEEN 

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KEEN is a great brand and online shop that sells men’s, women’s, and kid’s footwear. The shop offers impeccably made winter boots that are waterproof and packed with insulation to keep your feet warm in the winter months. The brand has a huge focus on manufacturing integrity, process standards, and workplace responsibility, to create a company that consumers can be proud to show off.

Joe Fresh

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Joe Fresh is a brand that you can count on for quality and comfort. Around the colder months, Joe Fresh releases a selection of winter boots for men, women, and children on its website and in-stores. With super affordable prices, it’s no wonder why this brand is such a fan favourite.

Eddie Bauer

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Eddie Bauer brings outdoor sports quality of footwear and offers it to everyone on its online shop. Focusing on sustainability, as well as inclusivity, to create a community where all consumers feel welcome. Eddie Bauer boots are produced with waterproof materials and have a great traction outsole.

Macy’s

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Offering a rather large winter boots selection, Macy’s typically has discounts that you don’t want to miss out on. The company also has a bunch of name brands like Sperry’s, Sorel, BEARPAW, Coach, and more.

Sorel

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Sorel has been producing ‘go-to’ winter boots for quite some time. With waterproof materials and packed with insulation, there’s no question as to why this shop is a top choice.

Altitude Sports

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At Altitude Sports you can search by whichever category of boot you’re looking for such as insulated hiking boots, waterproof winter boots, urban winter boots, and so much more. Explore all of the options and find which shoe works for you!

L.L. Bean

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L.L. Bean has so many wonderful winter boots for you to explore. Check out all of the different lengths, silhouettes, and colour-ways, made with awesome quality materials that will last you through winters to come.

The North Face

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The North Face has a variety of men’s, women’s, and children’s winter boots to browse. From tall boots, to ankle boots, there’s definitely one that is exactly what you’re looking for. If you’re searching for a modern and stylish look or a classic winter boot, The North Face has it all.

Sport Chek

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Sport Chek is full of classic winter gear brands like Helly Hansen, Columbia, Sorel, The North Face, and more. You may even score new boots at a discount or in the sale section of the site.

Columbia Sportswear

best winter boots
Facebook/Columbia Sportswear

Based in Portland, Oregon, Columbia Sportswear is a global outdoor brand that crafts active lifestyle gear combined with industry-leading technologies. The brand sells apparel, footwear, and accessories that reflect its Pacific Northwest heritage. Explore the abundance of boots for any type of weather.

Timberland 

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Timberland has become very well known for its classic workwear boots. The brand also has amazing hiking, waterproof, ankle, and winter boots to browse through. The winter boots are fully insulated to keep your feet nice and toasty in the cold weather.

Rudsak

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Orginially founded in Montreal, Rudsak, engineers its coats, boots, and more for the most vicious winter weather conditions. The brand only uses the finest luxe leathers, furs, and fabrics, trimmed with its signature hardware and details. You definitely won’t be disappointed when making your winter selection at Rudsak!

ECCO

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ECCO is such a great brand for high-quality winter boots. The brand even creates its very own leathers at its tanneries, so you know you can trust each and every one of its products. From short to tall boots, you’ll find something here that’ll match perfectly with your own style.

Soft Moc

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Soft Moc is definitely a great spot to check out if you’re on the hunt for winter boots. You’ll find footwear at all different price points from the best brands. Browse through selections from ugg, Blundstone, Clarks, Dr. Martens, Cougar, and more.

Pajar

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Pajar has a long history of making winter boots — 57 years to be exact. The Canadian brand is known for blending modern industrial design with old-world craftsmanship that will keep you warm and chic.

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The Boot Blowout Online Sale is officially here! Browse through classic styles and timeless designs in the men’s section. From now until Sunday, take advantage of the discounts and score yourself essentials to add to your footwear collection. FRYE boots are up to 70% off, so don’t hesitate, you can’t get these deals anywhere else! Also, sign up to be a member and score 10% off of your first purchase.

Don’t miss out on the weekend promo with code BUYMORE10 for 10% off when you buy two pairs of shoes and BUYMORE15 for 15% off when you buy three or more pairs.

Shop the sale at shop.styledemocracy.com until February 7 at 11:59pm EST.

Here are our top picks for men at the Boot Blowout online Sale.

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