mom wearing booties autumn steps; Courtesy of atdigit /Shutterstock
Tweens: 10-12 • Teens: 13-17

14 Cute Booties for Fall 2020

See recent posts by Amanda Norcross

Searching for a new pair of booties for your fall vacation (or just everyday wear)? We’ve found this season’s cutest and most comfortable booties to wear (while you’re inevitably chasing the kids around). These are the best booties for fall 2020.’
Women’s Wenda Cut Out Bootie; Courtesy of Target

1. Women’s Wenda Cut Out Bootie – Universal Thread

It’s all about the cut-out bootie in 2020, and we love the look of these ankle booties. The pointed toe gives them a feminine look, while the one-inch heel makes these shoes easy to walk around in. Available in six neutral colors, the Women’s Wendy Cut Out Bootie pairs especially well with cropped pants.

Miz Mooz Laurent; Courtesy of Zappos

2. Miz Mooz Laurent

What’s better than a good pair of fall booties? Sneaker booties. And we’re completely obsessed with the Laurent sneaker booties by Miz Mooz. These bootiesavailable in a wide range of colors and prints—are easy to slip on and off, and pair well with skinny jeans and a baggy sweater.

Sperry Crest Lug Zone Suede; Courtesy of Zappos

3. Sperry Crest Lug Zone Suede

The Sperry Crest Lug Zone Suede booties are another great choice for sneaker booties. Perfect to wear to everything from the Friday night football game to the airport, these comfortable booties feature a slouched look, exterior fashion zipper, and rubber sole. They come in blue, grey, and olive.

Miz Mooz Savvy; Courtesy of Miz Mooz

4. Miz Mooz Savvy 

These edgy, moto-style booties pair well with any fall look. The heel height (one inch) and foot cushioning make them wearable in any destination, and what’s not to love about the criss-cross straps? The Miz Mooz Savvy booties are available in seven styles.

Hush Puppies Women’s Mazin Cato Ankle Booties; Courtesy of Amazon

5. Hush Puppies Women’s Mazin Cato Ankle Booties

The Hush Puppies Women’s Mazin Cato Ankle Booties are classic and comfortable. They also come in any color you’d want to complete your fall or winter travel wardrobe. The inner linings can be removed for a better fit, if needed.

Steve Madden Women's Lancaster Western Boot; Courtesy of Amazon

6. Steve Madden Women’s Lancaster Western Boot

Looking for a pair of cute booties that’ll go with everything in your closet? Snag a pair of the Steve Madden Women’s Lancaster Western Boots. The deep side cutouts add an edge to these boots that pair well with a dress, jeans or even leggings. Buy them in black, grey, or cognac suede.

Sugar Women's Calico Ankle Bootie; Courtesy of Amazon

7. Sugar Women’s Calico Ankle Bootie

You can’t beat the price on these fall booties that feature the cutest cut-out design. The Sugar Women’s Calico Ankle Bootie—available in black, taupe, or grey—can also be worn in the spring and summer. Pair it with a long, flowy dress and denim jacket for an easy day-to-night look.

Clarks Clarkdale Dawn; Courtesy of Zappos

8. Clarks Clarkdale Dawn

Can’t decide whether you want black or brown fall booties? Get a bootie that features both! The Clarks Clarkdale Dawn booties have a black upper and a brown heel that makes them easy to match with neutral-colored clothing; they’re also great if you’re planning to pack a capsule wardrobe for your next trip. The best part? They have rubber soles and are easy to wear.

Steve Madden Troopa; Courtesy of Amazon

9. Steve Madden Troopa

The Steve Madden Troopa boot never goes out of style, making it a worthy investment (and a fairly affordable one at that). The combat-style boots have a one-inch heel and an interior zipper that makes them easy to pull on and off. Bonus: Steve Madden makes Troopa booties for kids, so you and your little one can match!

Frye Veronica Short Boot; Courtesy of Amazon

10. Frye Veronica Short Boot

Frye boots aren’t cheap, but they’re certainly worth the priceespecially if you’re looking for a stylish boot that’s built to last. Among our favorite styles is the Frye Veronica Short Boot, which comes in various colors and has a worn-in look. These rugged boots pair well with any fall or winter outfit.

Dr. Scholl's Women's Double ; Courtesy of Amazon

11. Dr. Scholl’s Women’s Double 

When it comes to comfort and affordability, you can’t go wrong with Dr. Scholl’s. If you’re on the hunt for a wedge bootie that won’t have you writhing in pain after an hour, try the Dr. Scholl’s Women’s Double. These sexy shoes come in black or brown, in both regular and wide sizes.

Fashare Women's Ankle Boots; Courtesy of Amazon

12. Fashare Women’s Ankle Boots

The Fashare Women’s Ankle Boots feature a triangle-stamped cutout and quarter-inch platform and are available in five different colors. Wear these faux suede booties with a flannel top and skinny jeans.

Fashare Women's Cutout Booties; Courtesy of Amazon

13. Fashare Women’s Cutout Booties

Can’t stop, won’t stop with the cut-out bootsnot when there are options such as the Fashare Women’s Cutout Booties! These playful booties feature a ruffle cut-out and come in 10 different colors.

Clarks Cazmin Hale; Courtesy of Zappos

14. Clarks Camzin Hale

The Clarks Camzin Hale booties have a leather and suede upper and a small heel. We especially love the criss-cross buckle that keeps these boots stylish… without ever going out of style. Did we mention there’s an OrthoLite® footbed? Sold!

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