Best Amazon October Prime Day Comfortable Shoe Deals 2024

October is here, and with it, a fresh Amazon Prime Day worth taking advantage of. From Tuesday, October 8 to Wednesday, October 9, the online retailer is hosting Amazon Prime Big Deal Days, a sitewide sale that gives Amazon Prime members rare savings opportunities. 

But if you don’t already have a Prime membership, don’t worry. You can still sign up for a free, 30-day trial that’ll give you access to hundreds of Amazon deals on everything from luggage sets and tech gear to fall clothes and — you guessed it — comfortable shoes. For a limited time, you can get best-selling travel shoes from brands like New Balance, Sorel, Brooks, Adidas, Puma… the list goes on and on. 

Best Amazon Comfortable Shoe Deals Overall 

Since holiday travel plans are in our future (and perhaps yours, as well), we’ll be using the sales event to stock up on travel-friendly footwear. You can save big on cozy, supportive shoes of all kinds, including these faux fur-lined Project Cloud Women’s Winter Boots, over 45 percent off, or these top-rated Asics Men’s Gel-Kayano 30 Running Shoes, on sale for $60 off the original price tag. With options starting at just $16, this list has a comfy shoe style for every traveler. To save you some time digging through page after page, we’ve handpicked 51 of the best, most impressive deals happening on comfortable sneakers, boots, and loafers. 

Best Amazon Walking Shoe Deals

Even if you only occasionally find yourself hitting the gym or running on the trails, it’s a great idea to have at least one pair of reliable, comfy athletic shoes in your rotation. And during Prime Big Deal Days, you can upgrade from your current pair all while saving money in the process. For example, the Brooks Women’s Glycerin 20 Neutral Running Shoes are $70 off, and these Under Armour Men’s Charged Assert 10 Running Shoes are starting as low as $55 — while supplies last, of course. 

• Asics Men’s Gel-Kayano 30 Running Shoes, $100 (originally $160)
• Feethit Men’s Slip-on Running Shoes, $36 (originally $46)
• New Balance Men’s 608 V5 Cross Trainers, $59 (originally $75)
• Adidas Women’s Run Falcon 3.0 Sneakers, $49 (originally $65)
• Under Armour Men’s Charged Assert 10 Running Shoes, $55 (originally $75)
• Brooks Women’s Glycerin 20 Neutral Running Shoes, $90 (originally $160)
• Asics Women’s Gel-Kayano 29 Running Shoes, $85 (originally $160)
• Saucony Women’s Ride 16 Sneakers, $70 (originally $140)
• Altra Women’s Lone Peak 7 Trail Running Shoes, $88 (originally $150)
• New Balance Women’s Fresh Foam Arishi V4 Running Shoes, $60 (originally $70)
• Brooks Women’s Adrenaline GTS 22 Supportive Running Shoes, $79 (originally $110)
• Under Armour Women’s Charged Assert 9 Running Shoes, $55 (originally $70)
• New Balance Women’s 608 V5 Cross Trainers, $65 (originally $75)
• Adidas Women’s Racer Tr23 Sneakers, $52 (originally $80)
• Puma Women’s Riaze Prowl Cross Trainers, $40 (originally $85)

Brooks Women’s Glycerin 20 Neutral Running Shoes

Brooks is a leading authority in the running shoe space. These Glycerin 20 daily trainer sneakers, currently $70 off, are a testament to the brand’s prestige with their nitrogen-infused V3 cushioned midsoles, enhanced air-mesh uppers, and an exceptionally lightweight build that bounces with every step. 

Puma Women’s Riaze Prowl Cross Trainers

You can score these Puma Riaze Prowl Cross Trainers for just $40 this Prime Day. They’ve got EVA cushioned midsoles, grippy rubber outsoles, and pull tabs on the tongues and heels for easy removal. 

Best Amazon Lifestyle Shoe Deals

Sometimes you just need a decent pair of everyday shoes to support you while you go about your day, whether that be running errands, clocking in hours at the office, or navigating a crowded airport. This October Prime Day, Amazon has hundreds of casual shoes on sale that are up for the task. You can pick up these top-rated Ryka Women’s Devotion Plus Walking Shoes for $30 off, or these podiatrist-beloved Dr. Scholl’s Women’s Madison Slip-on Sneakers, ringing in at just $36. 

• Ryka Women’s Devotion Plus Walking Shoes, $70 (originally $100)
• Skechers Men’s Ultra Flex 3.0 Slip-in Sneakers, $60 (originally $90)
• Dr. Scholl’s Women’s Madison Slip-on Sneakers, $36 (originally $80)
• Skechers Women’s Uno Stand On Air Sneakers, $55 (originally $79)
• Reebok Women’s Walk Ultra 7 DMX Max Shoe, $45 (originally $75)
• Crocs Men’s LiteRide 360 Pacer Sneakers, $39 (originally $65)
• Dr. Scholl’s Women’s Time Off Sneakers, $60 (originally $100)
• Skechers Women’s Bobs B Cute Shoes, $16 (originally $50)
• Nautica Women’s Tennis Shoes, $35 (originally $65)
• Cole Haan Men’s Grand Crosscourt 2 Sneakers, $60 (originally $110)

Skechers Women’s Bobs B Cute Shoes

Expand your comfy shoe rotation for just $16 with these low-top lace-up sneakers from Skechers. originally priced at $50, these versatile shoes have over 31,000 (yes, you read that right) five-star ratings for their comfort, style, and value.

Cole Haan Men’s Grand Crosscourt 2 Sneakers

These gorgeous court sneakers from Cole Haan are an impressive $50 off during Prime Day. Crafted with genuine 100 percent leather uppers, these sleek casual sneakers have a cushioned footbed and a fully lined interior that adds breathability and comfort. 

Best Amazon Loafers and Flats Deals

Easy to slip in and out of, loafers and flats are both convenient fall footwear choices for work and travel. For the next two days, Amazon will have plenty of elevated and more casual slip-on styles on sale — start with these supple leather Lifestride Women’s Margot Loafers for over 72 percent off, or these boat shoe-style Hey Dude Men’s Wally H2O Loafers for just $31.

• Dr. Scholl’s Women’s Nice Day Slip-on Loafers, $40 (originally $100)
• Hey Dude Women’s Wendy Linen Loafers, $24 (originally $42)
• Dream Pairs Women’s Revon Ankle Strap Ballet Flats, $29 (originally $51)
• Naturalizer Women Flexy Round-toe Ballet Flats, $35 (originally $79)
• Hey Dude Men’s Wally H2O Loafers, $31 (originally $70)
• Clarks Women’s Ashland Bubble Loafers, $37 (originally $85)
• Bruno Marc Women’s Penny Loafers, $17 (originally $36)
• Clarks Women’s Sharon Gracie Loafers, $45 (originally $95)
• Skechers Women’s Cleo 2.0 Love Spell Flatst, $36 (originally $57)
• Lifestride Women’s Margot Loafers, $19 (originally $70)
• Jousen Men’s Penny Loafers, $37 (originally $50)

Naturalizer Women’s Flexy Round-toe Ballet Flats

This classic ballet flat from Naturalizer has earned over 5,000 five-star ratings for its comfort and style, with one reviewer sharing that they’re “comfortable right out of the box” and are the “perfect work shoe.” These leather flats, on sale for $35, are constructed with a supportive, cushioned insole and a padded collar for all-day comfort.

Hey Dude Men’s Wally H2O Loafers

On sale for $31 are these preppy men’s slip-on loafers from Hey Dude. They have elastic laces that make slipping them on and off a breeze and have removable, memory foam cushioned insoles that provide supportive comfort in every step.  

Best Amazon Boots Deals

Fall is in full swing, so what better time to stock up on weather-appropriate footwear? Amazon had plenty of boots on sale for Prime Big Deal Days, with drastic price cuts on hiking boots — like these Columbia Women’s Newton Ridge Plus Hiking Boots, $53 off. Ahead, you’ll also find comfortable boots to snuggle up in this season, like these faux fur-lined Project Cloud Women’s Winter Boots, currently 45 percent off. 

• Merrell Men’s Walking Hiking Shoes, $87 (originally $170)
• Columbia Men’s Newton Ridge Plus Ii Hiking Boots, $57 (originally $100)
• Timberland Men’s White Ledge Hiking Boots, $100 (originally $120)
• Project Cloud Women’s Winter Boots, $55 (originally $100)
• Columbia Women’s Newton Ridge Plus Hiking Boots, $47 (originally $100)
• Chooka Women’s Waterproof Chelsea Boot, $30 (originally $37)
• Columbia Women’s Crestwood Hiking Shoes, $41 (originally $70)
• Men’s Nortiv 8 Hiking Boots, $54 (originally $90)
• Anjoufemme Women’s Lace-up Winter Boots, $50 (originally $65)
• Keen Women’s Targhee 3 Hiking Boots, $68 (originally $165)
• Keen Men’s Targhee 3 Hiking Boots, $86 (originally $165)
• Aomigoct Women’s Slip-on Winter Boots, $29 (originally $43)
• Timberland Women’s Mt. Maddsen Hiking Boots, $72 (originally $120)
• Salomon Women’s X Ultra Pioneer Hiking Boots, $91 (originally $150)
• Sorel Women’s Tivoli IV Waterproof Boots, $80 (originally $145)

Columbia Women’s Newton Ridge Plus Hiking Boots

These Columbia Newton Ridge Hiking Boots are a steal, ringing in at just $47, more than 50 percent off the original price tag. Featuring real leather uppers and traction rubber outsoles, these durable hiking boots have soft, cushiony interiors and have earned over 20,000 five-star ratings from Amazon shoppers alone. 

Project Cloud Women’s Winter Boots

Step into cozy comfort this winter with these plush suede ankle boots, on sale for $55. They’re made with genuine suede uppers and are fully lined with soft, fluffy faux fur that’ll keep your toes toasty all season long. 

Comfortable shoes aren’t the only products worth shopping during Amazon Prime Big Deal Days. You can save money on tech gear, travel essentials, luggage, and beyond — but don’t wait to pounce on something you love, because these deals end after October 9. 

Kimdi Women’s Suede Clogs

Skechers Women’s Go Walk Joy Sneakers

Lifestride Women’s Zee Loafers

Adidas Men’s Run Falcon 5 Sneakers

Sorel Women’s Out N’ About Waterproof Boots

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