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.
J.Crew
New Stevie Ankle Boots in Suede
These are the boots I'll be wearing on repeat this fall.
Madewell
The Dimes Kitten-Heel Boot
I already own these in black and can't wait to buy them in trending burgundy.
Seychelles
Acquainted Slouch Boots
Cute kitten-heel slouch boots to wear with your skirts this fall.
Marc Fisher
Iggy Kitten Heel Bootie
Polished and refined.
ZARA
Split Leather Kitten Heeled Ankle Boots
Suede boots are trending, and this chic Zara pair comes in at a reasonable price point.
H&M
Heeled Leather Boots
Toteme vibes. H&M prices.
Dr. Martens
101 Lace Up Boots
For stomping in those crunchy brown leaves.
Banana Republic Factory
Vegan Tall Slouch Boot
Luxurious, elegant, and so good for the price.
ZARA
Flat Split Leather High Tops
Your everyday fall boots, found.
Sam Edelman
Shea Over the Knee Boot
Love the idea of styling these with a boho ruffled dress.
Madewell
The Santiago Western Ankle Boot
Western styles are back for fall.
ZARA
Kitten Heel Knee High Boots
Wear with jeans and dresses alike.
MANGO
Leather Ankle Boots With Block Heel
It's time for an ankle-boot update.
Kenneth Cole
Meridith Knee High Boot
Rich chocolate brown is trending.
H&M
Boots
Throw them on and go.
Splendid
Janice Boot
Love this light gray.
Other Stories
Leather Ankle Boots
Classic and timeless.
FP Collection
Like Lightning Tall Boots
A chic pair of riding boots for the season.
H&M
Chelsea Boots
H&M's Chelsea boots are always top-notch.
Other Stories
Classic Leather Ankle Boots
Wear with your relaxed straight-leg jeans for a French-girl look.
Sam Edelman
Kinsley Motorcycle Boots
Lived-in moto boots were all over the fall runways.
Nordstrom
Dauphine Kitten Heel Knee High Boot
I want them in all three colors.
UGG
Classic II Short Boots
Is it even fall without a cozy pair of Uggs?
Steve Madden
Dollie Western Boot
Subtle Western boots in a gorgeous brown.
Steve Madden
Gleeson Moto Boot
Stomp in style.
Blundstone
Classic 550 Chelsea Boots
It doesn't get better than the quality of heritage brand Blundstone. The more you wear them, the comfier they get.
Franco Sarto
Marnie Kitten Heel Bootie
Sleek and sophisticated.
Linea Paolo
Tessa Lug Bootie
Try these if you're not into a super-chunky lug sole (like me).
Steve Madden
Boot Delvie
Black ankle boots for work, the weekend, and beyond.
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.