The Prettiest Ankle Boots Out There, Starting at $39

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(Image credit: Getty Images)

Sure, you probably have a few pairs of ankle boots in your collection by now, but why not add a few more? Exactly. After all, this is the one shoe silhouette that does the most work for you this time of year, so having a healthy assortment of the perfect pairs to work with every ensemble and occasion is worth it. But this doesn’t mean going out and dropping all your cash on brand-new styles (although if you want to, live your life). There’s actually a huge array of forward on-sale iterations out there upward of 60% off, starting at just $39. Keep scrolling to check out the prettiest ankle boots that are seriously discounted. But you better act fast; these won’t stick around for much longer.

Under $50

$50 to $100

$100 to $250

$250+

Next, check out five pairs of It boots that will sell out in a few weeks.

Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.