26 Chanel, Jimmy Choo, and Gucci Boots We Want Right Now for Under $300
There’s no denying it’s officially boot season. For now, you can let your strappy white Zara sandals hibernate until spring and focus on keeping your toes toasty as we head into the depths of winter (which, as a thoughtful reminder—officially starts in 30 days, friends!). If you haven’t already invested in a comfortable and chic pair of boots to keep you warm this winter, then now is the time.
If you’ve been hankering for a durable, comfortable, and luxurious pair of designer boots but don’t want to pay the hefty price tag for a brand-new pair, then I seriously suggest you head on over to The RealReal right now to score a used but undeniably stylish pair of designer boots at a much more affordable price point. The resale site's boot game is strong right now, and you can find all the chicest styles from Ferragamo, Celine, Stuart Weitzman, Isabel Marant and more.
But today I’m highlighting the best fashion-forward yet timeless boots from three classic and trending designers—Jimmy Choo, Gucci, and Chanel. Whether you’re looking for luxe leather knee-high boots to wear with your midi dresses this season, or you’re yearning for a cool pair of lug soles, or perhaps comfortable and classic black ankle boots are at the top of your wish list, then scroll below as I share the best designer boots hiding on The RealReal for under $300.
Up next, 17 outfits to wear with your black ankle boots.

Judith Jones is the associate shopping director at Who What Wear and has worked in fashion for over a decade. She specializes in shopping content and trend stories with high-affiliate impact. She shares the coolest, most desirable fashion market finds and brands for every budget. Previous to working in fashion, Judith worked as a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) sharing her passion for travel and culture.
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