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.
These are the boots I'll be wearing on repeat this fall.
I already own these in black and can't wait to buy them in trending burgundy.
Cute kitten-heel slouch boots to wear with your skirts this fall.
Polished and refined.
Suede boots are trending, and this chic Zara pair comes in at a reasonable price point.
Toteme vibes. H&M prices.
For stomping in those crunchy brown leaves.
Luxurious, elegant, and so good for the price.
Your everyday fall boots, found.
Love the idea of styling these with a boho ruffled dress.
Western styles are back for fall.
Wear with jeans and dresses alike.
It's time for an ankle-boot update.
Rich chocolate brown is trending.
Throw them on and go.
Love this light gray.
Classic and timeless.
A chic pair of riding boots for the season.
H&M's Chelsea boots are always top-notch.
Wear with your relaxed straight-leg jeans for a French-girl look.
Lived-in moto boots were all over the fall runways.
I want them in all three colors.
Is it even fall without a cozy pair of Uggs?
Subtle Western boots in a gorgeous brown.
Stomp in style.
It doesn't get better than the quality of heritage brand Blundstone. The more you wear them, the comfier they get.
Sleek and sophisticated.
Try these if you're not into a super-chunky lug sole (like me).
Black ankle boots for work, the weekend, and beyond.
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Here They Are: The 6 Biggest Boot Trends of Fall 2025Exotic finishes! Sock boots! Western motifs!
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Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do TooSee how fashion people from NYC to Paris to London wear them for fall.
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My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025Everything is under $100.
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If Reading Brontë in Central Park Is Your Vibe, Then You're Going to Love These 28 Fall Sweaters From Gap, Old Navy, and Banana RepublicStriped sweaters and cashmere.
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Wait, J.Crew Is 30% Off Sitewide Right Now—These Are the Chic Fall Pieces in My CartThe fall 2025 collection is so good.
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Shopbop Lovers to the Front—These 40 Styles Are Going to Be Huge This FallGive your wardrobe a fall facelift.
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My Mom Only Shops at T.J. Maxx and Marshalls—Here's What She Sent Me to Buy for Fall 2025She had me at under-$100 Uggs and Levi's.
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52 Elegant Fall Fashion Finds That Whisper Wealth But Don't Top $250Money talks.
