This post is all about 17 casual fall boot outfit ideas to keep you cozy and chic!
Boot season has made its way around again and you’re probably super excited to start styling them all cutesy and stuff.
There’s just something about slipping on a pair of boots and stepping out into that crisp fall air that makes everything feel instantly more stylish.
Whether you’re a fan of classic ankle boots, rugged combat boots, or the ever-comfy knee-highs, fall gives us all the excuse we need to mix, match, and strut. And let’s be real—boots just have a way of taking even the simplest outfits to the next level.
So, if you’re looking for a little inspiration to spice up your casual fall wardrobe, I’ve got 17 outfit ideas that will keep you comfy, cozy, and effortlessly chic all season long.
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Ankle Boots: The Everyday Essential
This may be controversial, but ankle boots are and have been the heroes of fall footwear. Their versatility makes them easy to pair with just about anything in your wardrobe.
They’re easy to slip on and style and, not to mention, oh so comfy! In recent years I’ve seen them being associated with millennial fashion, but I don’t necessarily think that’s true!
Yes, maybe the ankle boots and skinny jeans are not it anymore, but you can definitely wear ankle length boots a variety of ways – with cropped wide-leg jeans, paired with a cozy sweater over a ruffle dress, or with ankle length straight leg denim and a barn jacket, for example.
Pointy toe and square toe boots give a bit of an elongating effect, but you can’t deny that round toe ankle boots with a chunky sole (aka Chelsea boots), are incredibly comfortable!
Whether you’re keeping it casual with jeans or dressing things up, ankle boots add that perfect balance of comfort and style.
Sweater Dress & Jacket
Nothing beats the combo of a cozy sweater dress and boots. The boots bring a bit of structure to the relaxed silhouette of the dress, making it look put-together without sacrificing comfort.
Throw on a cute jacket for a cozier feel and you’ve got the perfect street casual look for Fall. You can also belt the dress at the waist for an extra umph, and throw on a scarf to complete the look.
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Jeans and Turtleneck Sweater
Channel a retro-chic vibe by pairing ankle boots with flare denim jeans and a cozy turtleneck sweater.
Flare jeans and heeled ankle boots were practically made for each other—hello, leg-lengthening magic! Throw in some oversized sunglasses and maybe even a chunky belt for good measure, and you’re basically the embodiment of casual cool.
Perfect for a coffee date or pretending you’re walking down a 1970s runway (because why not?).
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Get the Look:
Turtleneck Sweater and Plaid Coat
Nothing says “I’m ready for fall” quite like a turtleneck sweater paired with a cozy plaid coat and ankle boots. This combo is basically pumpkin spice in outfit form—but make it fashion.
The plaid coat adds that perfect pop of pattern, while the turtleneck keeps things sleek and warm. And let’s not forget the ankle boots—they undeniably pull the whole look together.
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Button-down Blouse and Trench Coat
You know those days when you want to look like you’ve got it all together, but in a totally effortless way? Enter the button-down shirt, ankle boots, and trench coat combo. It’s like “business casual” met “fall chic” and became best friends.
Throw on your fave light-wash jeans, step into those ankle boots, and toss on the trench coat for that I just rolled out of bed but still look fabulous look.
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Switch out the heeled boots for a pair of comfortable Chelsea boots for a casual chic look that is sure to get you through a full day of walking without the foot pain.
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Oversized Sweater and Ugg Ankle Boots
If there were an award for the ultimate cozy-girl fall look, the sweater and Ugg ankle boots combo would win hands down.
Pair it with jeans, leggings or joggers, grab your favorite pumpkin-spiced drink, and you’re set for a day of casual fall adventures—aka looking adorable while doing absolutely nothing.
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Mid-Calf Boots: The Cool-Girl Favorite
Mid-calf boots are having a major moment this fall. They hit that sweet spot between ankle boots and knee-highs, making them perfect for transitioning from warmer days to cooler evenings. Plus, they add an instant cool-girl vibe to any outfit.
Plaid Pants and Sweatshirt
Who says plaid pants are just for holiday parties? Pair them with a cozy sweatshirt and some mid-calf combat boots for a look that screams fall cool without even trying.
The boots give this comfy outfit the perfect edge, while the plaid pants are cozy and stylish. Toss in a messy bun and some oversized sunglasses for a maximum effortless feel.
Whether you’re running errands or just trying to convince yourself to leave the couch, this combo is your secret weapon for looking chic while feeling like you’re in pajamas.
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Denim Skirt and Sweatshirt
Ready to channel that laid-back Americana vibe? Grab your favorite denim skirt, throw on a slouchy sweater, and slide into your trusty Frye Campus boots.
These mid-calf beauties add just the right amount of rugged charm, while the denim skirt and sweater keep things playful and relaxed.
It’s the perfect outfit for a crisp fall day when you want to feel nostalgic and stylish—kind of like you’re about to hop into a vintage truck and drive through scenic fall foliage.
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Knee-Length Boots: Chic & Timeless
Knee-high boots have stood the test of time for a reason—they’re chic, timeless, and always make a statement.
Whether you prefer flat heeled boots or sleek heeled ones, knee-highs bring drama and elegance to any fall outfit.
Mini Skirt & Sweater
The ultimate fall boot outfit has entered the chat. For a bit of drama or gossip girl vibes, pair knee-high boots with a mini skirt and a cozy oversized sweater.
The contrast between the short skirt and tall boots creates an eye-catching look, while the long coat balances everything out.
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Get the Look:
Trench Coat & Sheer Tights
Switch up the look a bit by adding some sheer tights and a trench coat. Choose a plaid or camel coat to keep things seasonal and add a cozy knit scarf for a final fall flourish.
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Knee High Boots & Denim Dress
Go for a classy look by pairing a chic denim dress with suede heeled boots.
Denim Skirt and Denim Button Down
Another variation of this classic look is styling denim shorts with a denim button down. You get the same chic effect with more casual pieces that are wardrobe staples.
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T-Shirt & Mini Denim Skirt
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Ruffle Skirt & Denim Jacket
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Boots & Fall Go Together Like Pumpkin & Spice
And there you have it—17 easy, cozy, and effortlessly chic ways to rock your boots all fall long!
Whether you’re strutting in ankle boots, slouching into mid-calf styles, or making a statement in knee-highs, there’s a look for every mood (and every pumpkin patch visit).
Fall fashion is all about layering up, staying comfy, and looking like you just casually rolled out of a Pinterest board.
So, go ahead—grab those boots and mix and match your favorite outfits!
Xoxo,
Diana Colibri
