Tuesday, November 25, 2025
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    UGG, Steve Madden, Quince & More

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    Chelsea boots have been around forever. They’ve been worn by everyone from The Beatles to Kendall Jenner.

    Although Chelsea boots have evolved, they’re just as stylish and timeless as they’ve always been. No matter what form they take, the classic Chelsea boot is the winter shoe that will never let you down.

    The ankle boot comes in every heel height, material, and style you can think of, and pair well with everything from tailored trousers to barrel jeans.

    Wear a trendy brown suede pair with a fair isle sweater or go for sleek leather black boots with cigarette jeans and a cropped trench. And rock a heeled style with a dress for an edgy yet sweet look. Either way, you’ll look effortlessly chic.

    Whether a pair of block heel booties or ones with a chunky rubber sole, now’s the perfect time to grab a pair for less, because so many brands are running Black Friday and Cyber Monday sales right now. Think Dr. Martens, UGG, Sam Edelman, Dolce Vita, Steve Madden, Aldo and more.

    Find your perfect pair. Shop the best Chelsea boots, starting at $40.



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