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The 7 Best Boots to Style with Leggings Right Now — Under $300

Cole Haan black boots

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Even though I live in Southern California, I’m still California dreamin’ on such a winter’s day! It’s been super chilly all over the U.S. lately, so it looks like our winter wardrobe is here to stay for the foreseeable future. If you’re like Us, then that means boots and leggings on repeat! Cozy style is our daily uniform.

But finding the right boot to rock with leggings is not as easy as you might think. Many of our beloved boots are sadly too short, hitting our ankles at an awkward spot and throwing our proportions off. The key is wearing boots that elongate our legs for a flattering silhouette.

Below are seven of our favorite boots for Zappos that pair perfectly with leggings!

Sam Edelman Penny 2 Wide Calf Leather Riding Boot

Sam Edelman boots


Go along for the ride in these sleek riding boots by Sam Edelman! Designed for wider calves, these leather boots are sturdy and sophisticated.

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Madewell The Poppy Tall Lugsole Boot

madewell boots


Lug sole boots are totally trending right now! These chunky tall boots from Madewell will add some instant edge to your ensemble.

Was $348On Sale: $292You Save 16%
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Naturalizer Jessie Wide Calf

Naturalizer boots

Detailed with gold hardware, these buckled boots are fierce and fabulous! These leather boots are also ideal for customers with wider calves.

Was $225On Sale: $113You Save 50%
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Cole Haan Clive Stretch Boot

Cole Haan boots

These Cole Haan stretch boots are seriously stylish! Featuring an elastic gore panel, cushioned footbed and zippered closure, this boot is just as comfortable as it is chic!

Was $210On Sale: $149You Save 29%
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LifeStride Xtrovert Wide Calf

Lifestride wide calf boots

Water-resistant for wider calves, these faux-leather boots are ideal for rain or shine! The back stretch panel and side zipper also allow for easy on-off access.

Was $100On Sale: $77You Save 23%
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Ugg Harrison Tall Boot

Ugg leather boots

One footwear brand that never lets Us down is Ugg! These knee-high boots are made with waterproof leather and recycled materials.

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LifeStride Bristol Boot

Lifestride boots

Level up your boots collection with these stack heel boots! The comfort footbed and stretchable back panel provide flexible movement and all-day comfort.

Was $120On Sale: $101You Save 16%
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Bonus: Dr. Martens Floral Mash-Up Boots

floral Dr. Martens boots

Put a spring in your step with these floral boots from Dr. Martens! These stylish shoes will add a fun pop of color to your #OOTD, right in time for warmer weather. You can rock these Docs all year long!

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Nordstrom Has So Many Boots and Sweaters on Sale — Shop Our Faves!

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Looking for additional ways to elevate your closet? Check out more picks below:

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