Our Top 10 Lists help shoppers quickly and easily find what they need. Using an intense review and approval process (which you can learn more about here), we break down the best styles according to what consumers most commonly search for and want.
Shoe trends come and go, but one of our forever favorites for fall is the Chelsea boot. Originally designed for Queen Victoria, the chunky-sole boot made perhaps one of the longest-lasting trend comebacks we've seen during the 1960s. Clearly, this essential shoe won't be finding itself in the giveaway pile any time soon. It's pretty easy to see why, too. The beloved bootie is the perfect blend of fashion and function with an added touch of cool-girl edge and—trust us—you can expect a lot of compliments when you're rocking a pair. From stacked heels to pointed toes and luxe leathers, there's something to be said about the stylistic simplicity of slipping on a pair of Chelsea boots, which is why we want to help you find your perfect fit. To help you do just that, we've utilized our handy dandy algorithm to find the Top 10 Chelsea boots you can shop right this very second. Our selection of women's Chelsea boots includes must-have features like waterproof exteriors and stretch-to-fit inserts to ensure they're made for equal parts walking and style. Keep scrolling to shop the best Chelsea boots of 2021 you need in your winter wardrobe. Opening image: everlane.com
Did you find your dream pair of boots on our 10 Best Chelsea Boots For Women? Keep shoe shopping and check out our 10 Best Tall Boots too!
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Blundstone Footwear Original Series Water Resistant Chelsea Boot
WHY YOU NEED IT: Blundstone Chelsea boots are the definition of classic. On top of that, this particular pair is raved about for its serious comfort and ability to withstand the weather.
BEST FOR: If you're in the market for a high-quality pair of women's Chelsea boots, you can't go wrong with Blundstone. The long-lasting leather design is perfect for everyday wear and comfort.
Vince Henderson Weatherproof Chelsea Boot
WHY YOU NEED IT: These platform Chelsea boots effortlessly elevate any outfit, even through puddles and drizzly skies.
BEST FOR: Umbrella forgetters, these are for you—they're the best waterproof Chelsea boots to wear on a rainy day and even when there's not a cloud in sight.
Everlane The Italian Leather Square Toe Chelsea Boot
WHY YOU NEED IT: Hello, luxury. These Chelsea ankle boots are made with 100% full-grain Italian leather and a timeless shape that'll last for seasons to come.
HELPFUL TIP: These booties have a narrow fit, so be sure to check the sizing in the product description to ensure you get the perfect pair.
Madewell The Citywalk Lugsole Chelsea Boot In Leather
WHY YOU NEED IT: Cloudlift Lite padding and durable leather makes these Chelsea boots ideal for conquering winter outings that have you on your feet all-day long.
USER REVIEW: "I immediately fell in love with these boots online and in person. They fit like a dream and no BREAK in needed. I live in these boots and highly recommend as not only are they stylish but they are 100% functional."
Caslon Miller Water Resistant Chelsea Boot
WHY PEOPLE LOVE IT: No matter the weather, these boots can handle it. At $100, they're a total steal.
USERS SAID: "Love, love, love these! I have pretty much worn these boots since I've gotten them back in October. I'm 5'3, and I've tried on other Chelsea boots, but they've always gone up too high. These hit perfectly for the cropped jeans I have. They slip on so easily and are very comfortable to wear all day. They're also true to size unless you want to wear thick socks."
Sorel Cate Chelsea
WHY YOU NEED IT: No slip-on struggles here. Designed with elastic side panels and a leather heel tab, these boots provide pull-on ease for getting dressed in a flash.
HELPFUL TIP: These boots have a narrow fit, so be sure to review the sizing recommendations for the best match.
Madewell The Ainsley Chelsea Boot
STYLE WITH: Aren't these ankle booties just darling? We'd pair them with our favorite slip skirt.
HELPFUL TIP: These boots have a narrower fit but will stretch with wear. We recommend sizing up if you have a wider foot or want to style them with thicker socks.
Madewell The Regan Boot
LOVED FOR: These boots were made for walking—literally. This block heel is surprisingly walkable, and not to mention irresistibly cute.
WHY YOU NEED IT: Kiss sore feet goodbye. Madewell added an extra layer of padding to make these boots extra comfy.
Dr. Martens Flora Leather Chelsea Boot
LOVED FOR: Dr. Martens will never go out of style. The timeless and classic design has been loved for decades.
USERS SAID: "This is my first pair of Dr. Martens, and after 16 months of ownership, I'm still impressed by the style, durability, and comfort of these boots. The Flora has a thinner version of the classic Dr. Martens sole, which makes the shoe look a bit more formal. In addition, the almond toe of these boots offsets the wider footbed typical of Docs and keeps them looking neat even in smaller sizes."
Marc Fisher LTD Yale Chelsea Boot
WHY YOU NEED IT: Meet the modern Chelsea boot. Sleek details like a pointed toe and clean lines add a touch of sophistication and polish to these beauties, providing timeless appeal.
LOVED FOR: The elastic goring makes pull-on style possible so you can get booted up in a flash.
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