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When you buy through our links, Business Insider may earn an affiliate commission. Learn more Along with a pair of nude pumps and classic white sneakers , a trusty pair of ankle boots is a must-have in any wardrobe. Their versatility is almost unmatched: not only can they transition from brisk fall well into warmer spring days, but they also look equally chic with jeans and leggings as they do with skirts and dresses.

But let's face it: not all ankle boots are worth your investment. The best ankle boots are just as comfortable and durable as they are stylish. Ahead, we rounded up a handful of styles that check both boxes — from winter-ready waterproof options and everyday Chelsea styles to splurge-worthy suede booties.



If you're in the market for boots with a taller shaft, see our piece on the best knee-high boots . A quick look at 5 of our favorite ankle boots Everlane's Day Boot is a buttery soft, true to size, walkable closet staple that's perfect for everyday wear. It's one of our favorite shoes from the brand, even after testing nearly every pair Everlane has made in recent years.

Winter is no match for these waterproof and warm Chelsea boots. Blundstone paired their classic aesthetic with a sheepskin footbed that is a godsend when it's freezing outside. Plus, they sell versions without the lining if you live in a milder climate.

These stretchy boots from Vivaia are exceedingly comfortable, water-repellent, and made of an elastic outer that can accommodate wide feet. W.

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