I'm a Fashion Editor—These Are the Chicest Under-$250 Boots in My Shopping Cart RN

So long. Farewell. Arrivederci, sandals. This weekend, fall officially begins, and that can only mean one thing. Boot season is finally here. For the next six months, it's very possible you'll be wearing boots daily—whether it's a thigh-high pair with a boho dress or chic black leather ankle boots with your wide-leg jeans—so you may be looking to add a fresh pair or two to your wardrobe, which is where we can help.
While an amazing pair of boots can certainly be an investment purchase, we don't think the investment has to take everything you budgeted for a fall wardrobe. Instead, I went on the hunt for the chicest boots of the season and found these 29 pairs for under $250. Included are timeless and classic pairs as well as styles that hit on this season's biggest trends. If you're looking for a new pair of boots to mark the season, then keep scrolling for the chicest styles that won't break the bank.

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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