The Absolute Comfiest Fall Shoes Up to 79% Off on Amazon


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After a summer of wearing thin flip-flops and painful heels, it only makes sense to opt for comfortable shoes this fall. With Amazon Prime Big Deal Days right around the corner, the e-tailer is a one-stop shop for your footwear needs. The two-day savings event lasts from Tuesday, October 7, to Wednesday, October 8, but there are red-hot deals to grab now!

From celeb-approved brands to designer-looking styles with an affordable price tag, we found 16 of the comfiest fall shoe deals on Amazon. Say goodbye to pain and discomfort when you check out our top picks.

The Absolute Comfiest Fall Shoes on Sale Before Fall Prime Day

Elevated Shoes

1. Our Favorite: Serve off-duty model style in these soft and comfy ballet flats — was $35, now $27!

2. Versatile Comfort: These Mary Jane flats feature a plush, moisture-absorbing insole. A classic silhouette makes them perfect for everyday wear — was $36, now $30!

3. Metallic Moment: Sparkle with each step you take, thanks to the metallic finish on these square-toe flats — was $70, now $49!

4. Biggest Splurge: Save big on these Lucky Brand ankle booties — was $129, now $88!

BERLIN, GERMANY - SEPTEMBER 1: Sonia Lyson is seen wearing a long, oversized black coat with broad shoulders and a straight cut, worn open from 032C; a simple black crop top leaving the midriff slightly visible from Zara; a short, fitted black-and-white polka dot mini skirt from Attega; black chunky loafers paired with white socks from LeGer by Lena Gercke; a medium sized white leather handbag with shoulder straps from Demmilie London; small, sleek black sunglasses that are oval shaped from Vela Eyewear; her brown hair is pulled back into a slightly messy low bun on September 1, 2025 in Berlin, Germany. (Photo by Moritz Scholz/Getty Images)

Related: The Best Early Amazon October Prime Day Deals on Rich-Looking Loafers

Amazon’s Prime Big Deal Days event is a few weeks away, however, the retailer is already cutting prices on one of the chicest categories for fall: loafers. The polished shoe staple is making a huge comeback, and thanks to early October Prime Day markdowns, you can snag options that look designer without the high-end price […]

5. Breathable Fabric: If you live in a warm climate, these knit Mary Janes will offer relief through the fall and beyond — was $43, now $24!

6. All About Autumn: Deliver a fall-approved look in these timeless suede loafers — was $37, now $34!

Casual Shoes

7. All Day Wear: Whether you’re working long hours or you’re on a hot girl walk, you’ll love these comfy sneakers for it all— was $70, now $40!

8. Big-Budget Lookalike: We love these suede clogs because they look similar to a style worn by Meghan Markle and Jennifer Aniston. These comfy shoes feature a cushioned cork footbed and arch support — was $50, now $30!

9. Furry Find: These cozy ankle boots have plush fur lining to keep you warm when the weather cools down each fall — was $65, now $40!

10. Vintage Aesthetic: Combine comfort and style in these retro-looking sneakers. We love the low-profile silhouette and comfy memory foam insole — was $50, now $38!

11. Bestseller: These Adidas VL Court sneakers are so trendy and comfy, they earned Amazon bestseller status — was $70, now $65!

Jennifer Aniston attends the Los Angeles Premiere Of Netflix's "Murder Mystery 2" at Regency Village Theatre on March 28, 2023 in Los Angeles, California.

Related: Jennifer Aniston’s Effortlessly Cool New Balance Sneakers Are Back on Amazon

Jennifer Aniston always inspires Us with her effortless, cool-girl style. From timeless wardrobe staples to her must-have accessories, she’s a master at making casual looks feel elevated. And this season, one her closet MVPs are finally back in stock — and on Amazon. It’s no surprise that Aniston’s go-to sneakers keep selling on the major […]

12. Lace-Free: We love these Dr. Scholl’s Madison sneakers because they feature a slip-in easy design that makes putting them on a breeze — was $80, now $55!

13. Pillow Soft: Going hiking? Perhaps you’re training for a turkey trot. These Better Foam Prowl slip-ons feature a soft foam insole and sock-like fabric for ultimate comfort — was $65, now $40!

14. A-list Pick: Reese Witherspoon is a huge fan of Brooks sneakers. Her go-to brand marked down the bestselling Ghost 16 running shoes — was $140, now $90!

15. Trending Topic: Deliver a street-style-approved look in these influencer-loved New Balance 608 V5 sneakers — was $80, now $60!

Comfortable Work Shoes

Related: 13 Cushioned Work Shoes That Feel Like Walking on Clouds

Commuting to work is no easy feat. Whether you carpool or use public transportation, wearing comfortable shoes makes the trek go by smoothly. With that in mind, we found 13 cushioned shoes on Amazon that feel so soft and plush, you’ll feel like you’re walking on clouds. Whether a pair of comfy sneakers fits the […]


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