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.
-
Forget Parisian Style—Every Chic Person Is Wearing This Fall Aesthetic InsteadChic, charming, and calming.
-
I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds From Nordstrom, Zara, and H&MDid I mention they're under $250?
-
Sorry to My Classic Black Shoes, But This Printed Shoe Trend Is Defining Fall 2025Spotted on fashion people in Venice, NYC, and Copenhagen.
-
Old Navy Just Launched Its New Fall Handbag Collection—and It Looks RichSoft faux suedes and sophisticated silhouettes.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall ClosetStylish sweaters and suedes ahead.
-
I Just Spent Hours Scrolling Saks—25 of the Chicest Pieces I'm Eyeing for FallMy September wish list.
-
What to Buy for Fall If You Don't Want to Regret It Next Year (or the Year After)Investments only.
-
The Top 10 Things to Buy This September If You Want Cooler Outfits and More ComplimentsFall is in full swing.
