37 Comfortable Shoe Deals on Amazon for September

If you’re like me, finding the right shoes for traveling can be tricky, especially when you love fashion but can’t stand uncomfortable footwear. Striking the perfect balance between style and comfort has become my personal mission when shoe shopping. And, of course, price is a factor, too. That’s why I’m always scrolling through Amazon for deals on shoes for my fall travels and beyond (living in NYC means I walk a lot on the daily). With different shoes for every occasion, it’s essential to have comfortable options for it all. 

For example, if I’m going for a walk through Central Park, I never leave the house without my running shoes — I need extra cushion for my flat feet. But if I’m heading out on a fall trip and want to look stylish while staying comfy, I go for a lifestyle sneaker that blends function with fashion. The same applies to cozy boots and cute flats — both of which are having a major moment this season. Since I already did the work for myself, I rounded up the 37 best comfortable shoe deals on Amazon for you, too.

Best Overall Comfortable Shoe Deals

There are endless options when it comes to choosing travel shoes — and the right pair depends on the occasion. The one constant? Comfort is always key. While I’ve broken down the best travel shoes by category, these are the top five overall. Whether you’re strolling through a new city, heading out to dinner, or embarking on a hiking adventure, we’ve got you covered with the perfect pair. 

Best Running Shoes Deals

Wearing the wrong running shoes can cause more than just short-term soreness — it can lead to long-term foot problems, as well. That’s why we’ve rounded up the most comfortable running shoes to help keep you moving. With options from trusted brands like Brooks, Adidas, and Asics, these shoes can offer reliable support and incredible cushioning, whether you’re hitting the pavement or the treadmill.

Brooks Women’s Glycerin 20 Neutral Running Shoes

SDolphin Men’s Running Shoes

Best Hiking Boots and Shoes 

Fall is the perfect time for hiking, and proper footwear is a must. Investing in quality hiking shoes is a well-known travel hack, and right now, there are plenty of deals available. The Nortiv 8 Women’s Hiking Boots are not only waterproof and durable, but they also add a stylish touch to your outdoor gear. Plus, the Columbia Women’s Newton Ridge Hiking Shoes are 45 percent off — grab a pair while the sale lasts.

Columbia Women’s Newton Ridge Hiking Shoes

Nortiv 8 Men’s Hiking Boots

Best Boots Deals

Boot season is here, and I can’t get enough of all the stylish options that’ll last all fall and well into winter. Not only do boots keep your feet warm, but they also add a chic touch to any outfit, making them ideal travel shoes. Low boots, like the Decarsdz Women’s Chunky Chelsea Boot, which are currently 60 percent off, pair effortlessly with jeans and a cozy sweater. For a dressier look, the Dream Pairs Women’s Knee-high Boots, now 30 percent off, would look stunning with a sweater dress.

Stq Women’s Combat Lace-up Boots

Globalwin Women’s Biker Boots

Best Lifestyle Sneakers

When traveling, lifestyle sneakers are a must, but it’s important to strike the right balance between style and comfort. Luckily, Amazon offers plenty of adorable sneakers that not only keep your feet happy but also elevate your outfits at a great price. One of my top picks is the Sam Edelman Women’s Layla Sneakers, which are 30 percent off. They’re neutral with a pop of black, adding a subtle flair to any outfit. Another great option is the Puma Women’s Carina Sneakers, an all-white classic that goes with everything in your suitcase.

Puma Women’s Carina Sneakers

Adidas Men’s Stan Smith Shoes

Best Flats

Flats have become a staple in my wardrobe, especially heading into fall — they offer the comfort of sneakers but with a more elevated look. Pairing flats with cropped jeans, a simple tee, and a cardigan is chef’s kiss. The Hush Bubbie Women’s Flats, now 49 percent off, are a fantastic option, as are the Sam Edelman Women’s Micah Mary Jane Flats, which are 47 percent off. Both styles are versatile, simple, and timeless classics.

Hush Bubbie Women’s Flats

Skechers Women’s Plush Flats

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