It’s almost fall, which means it's time to put away your flip-flops and pull out your ankle boots. What else pairs so perfectly with your entire fall wardrobe of cozy knits, plaid and denim? Ankle booties often hit the triple digits, but we found 17 stylish, versatile and walkable pairs for under $100. Happy fall!
1. Vionic Madeline Ankle Boot
Does everyone here know about Vionic? Everyone should know about Vionic! The podiatrist-approved shoes are specifically designed to prevent foot pain, especially biomechanical issues like plantar fasciitis or flat foot. Vionic’s cute, classic Madeline bootie offers springy padded footbeds for off-the-charts comfort, plus side zippers and fun tassels for fall-time strutting.
2. Chinese Laundry Finn Bootie
With an on-trend silhouette, elastic side panels for easy wear and a durable 2-inch stacked heel, the Finn Bootie by Chinese Laundry hits that rare stylish-slash-comfy sweet spot. The dress-up or dress-down bootie looks just as good with jeans and an oversized sweater as it does with a pencil skirt and a blazer.
3. DailyShoes Cowgirl Bootie
In our fall fantasy, we’d be stomping around the state fair in these short cowgirl boots. Since that’s shelved for 2020, we’ll just have to rock the boots for everything else — fall-foliage trips, backyard bonfires and evening strolls to check out neighborhood Halloween displays. The back zipper makes getting them on and off a cinch and the soft lining helps with all-day wear.
4. Old Navy V-Shaped Ankle Booties
Old Navy’s cutout booties may not be handcrafted in Tuscany or anything like that, but the fans of the brand know it delivers comfort, durability and style for a super-affordable price. The footbed of its V-Shaped Ankle Booties is surprisingly comfortable and the stacked heel gives a good bit of lift.
5. Lucky Brand Paramo Bootie
If you dig the cutout style but want a slightly tougher version, give Lucky Brand’s Paramo bootie a try. It skews more all-purpose Chelsea boot, with a cool neutral shade that will hide inevitable scuffs.
6. SNJ Lug Sole Combat Boots
With a thick heel and rubber sole, this combat boot is made for autumn romps. Thanks to the side zipper, you don’t have to contort your body into a pretzel to get them off at the end of the day.
7. Marc Fisher Hopee Bootie
Your fall agenda may be a little different this year, but it still can include hiking and planting fall annuals in the yard. Marc Fisher’s suede lace-ups can handle both of these fall activities and more: its faux-fur lining keeps your toes toasty and the lugged sole helps you keep your footing wherever you go.
8. Dream Pairs Chunky High-Heel Booties
Want to wear two trends at once? This affordable Amazon pick is essentially a sock bootie, and it comes in a leopard print that dials the head-turning factor up to a 10. In fact, tons of happy Amazon shoppers mention how many compliments the booties get them — though some recommend adding insoles for serious walking.
9. Toetos Chicago Ankle Bootie
Stylish, casual and under $30, these sweater-weather-ready booties are perfect for fall. The inside lining gives some padding and sneaky inside zippers let you kick ‘em off without a fuss. The lacing at the sides elevates the boot’s overall style and adds major boho vibes.
10. Soda Perforated Ankle Booties
Want your getting-dressed process to be as low-key as possible these days? Embrace the ankle boot. At $35, Soda’s block-heel bootie is an excellent place to start. Throw the low-rise pair on with fitted jeans and a flannel and you’ll be out the door in minutes flat. We love the flirty cutouts (great for keeping things airy and breathable) and the super-sturdy block heel. Need more convincing? Check out the more than 1,000 five-star reviews on Amazon.
11. Shoes for Crews Elva
If you like your practicality with a bit of edge (and a great price), this adorable "shootie" should suit you well. The water-resistant slip-ons have elastic side panels to help get them on and off, lined footbeds for extra comfort and chunky rubber 2-inch heels that soften the impact of each step. The streamlined design hits right at the ankle and goes with everything from midis to mom jeans. Note that they run narrow, so consider sizing up.
12. Toms Kala Oxford Booties
Toms’ Kala Booties have everything we look for in a fall shoe: sneaker-like comfort, cushy footbeds that cradle our feet and a range of great neutrals that just beg to be worn with a warm, cozy poncho. The suede-wrapped wedge heel is made for people who don’t do heels.
13. Dirty Laundry Lisbon Sedona
Looking for a don’t-mess-with-me shoe? Say hello to Dirty Laundry’s tough-as-nails Lisbon Sedona bootie. Shoppers report that they’re as comfortable as they are stylish (thanks to the rugged sole and chunky heel) and that the shaft is fitted enough to wear under skinny jeans.
14. Sbicca Kathrin Boots
Wanna strut around like Kate Hudson in Aspen? Nab these boho-chic cuties — for little more than your afternoon pumpkin spice latte. Interior padding and a stacked heel are certainly walking-friendly, but it’s the knotted fringe that really makes these boots.
15. Fergalicious Bonus Bootie
No need to choose between style and function with this adorable ankle boot. The perforated design is perfect for transitional weather (no overheated feet here) and the side cutouts add just the right amount of sass. Practical details include the walkable stacked heel and back zippers.
16. Lucky Brand Glanshi Ankle Boot
Sensing a trend? Lucky Brand is a great go-to for all things ankle boots. Its no-nonsense Glanshi style works in all seasons and with just about any outfit — jeans and a tee, leggings and a hoodie or a dress and statement earrings. The profile is chic, understated and goes with anything, while the memory foam insoles provide some cushy bounce underfoot.
17. Skechers Lasso Caravel
A pair of stitched suede booties is one surefire way to get pumped for fall. In the case of these ankle boots by Skechers, a round toe and fabric lining provide breathing room. Memory foam footbeds, a low block heel and a rubber outsole keep you secure and pain-free, whether you’re running errands or weaving through a corn maze.
For more stories like this, check out:
- Reese Witherspoon wore the perfect everyday sneaker
- Over 4,000 people love these $17 shoe inserts — and podiatrists approve
- I'll be wearing this $14 sock-shoe hybrid for the rest of the summer
To discover more deals, shopping tips and budget-friendly product recommendations, download the new TODAY app and subscribe to our Stuff We Love newsletter!