47 Comfy Travel Shoes on Sale for Amazon Prime Big Deal Days

I love to buy a few new things right before a trip, but I’ve learned the hard way that bringing a new pair of shoes on vacation doesn’t always work out well. I’ll never forget spending six miserable hours walking around San Juan, Puerto Rico, in a pair of flats I hadn’t yet broken in—and of course, ending up with a painful blister. 

That’s why I’m always down to take recommendations on comfortable travel shoes. So, today, I’ll be that friend for you. Amazon’s October Prime Day event, officially known as Amazon Prime Big Deal Days, kicked off today, and there are thousands of shoes on sale, meaning you can’t let the sale end without grabbing a pair or two. So, I scoured Amazon’s inventory to find the most comfortable shoes on sale right now, including deals on sneakers, slip-ons, flats, hiking shoes, boots, and more from brands like Nike, New Balance, and Vionic. 

If you find your size and preferred color in a pair of shoes, you know the deal—shop quickly if you don’t want it to sell out. Here are the 47 most comfortable shoes on sale for the fall edition of Amazon Prime Day. 

Best Amazon Prime Day Deals Overall

• Sellout risk: Ryka Women’s Podflow EZ Sneaker, $67 (originally $120)
• Rare find: On Women’s Cloud 5 Sneakers, $167 (originally $230)
• T+L trusted brand: Vivaia Allday Unisex Slip-on Mesh Sneakers, $159 (originally $169)
• Most stylish: Sam Edelman Women’s Michaela Stud Mary Jane Flats, $79 (originally $130)
• 69 percent off: Lucky Brand Women’s Basel Ankle Bootie, $40 (originally $129)
• Editor-loved walking shoe: Kizik Vegas Slip-on Sneakers, $80 (originally $129)
• Podiatrist-approved: Vionic Women’s Winny Sneaker, $69 (originally $125)
• Under-$25 find: Inpaksa Women’s Platform Mini Boots, $23 (originally $32)
• For relieving foot pain: Oofos Oomg Slip-on Recovery Shoe, $100 (originally $140)
• Cozy fall find: Dearfoams Fireside Shearling Perth Foldover Boot, $97 (originally $140)

Amazon’s Big Prime Deal Days event features discounts on shoes that rarely go on sale, like On’s Cloud 5 Sneakers. Now 27 percent off, the lightweight and breathable shoes are designed with special zero-gravity foam that minimizes pressure on your feet as you get your steps in. Similarly, the Ryka Women’s Podflow EZ Sneaker is also designed for comfortable all-day wear. The shoes feature a unique midsole with special pods that support each part of the foot and your natural stride, and they’re 44 percent off right now. There’s much more on sale besides just sneakers, though. If you’re looking for something a little dressier, the Vionic Uptown Loafer offers a great balance of comfort and style. Designed with a lightweight cushioned insole, the shoes are also available in 15 color options (though not all are discounted). Grab it for up to 51 percent off right now. See a ton of other deals below. 

Best Walking and Running Shoe Deals

If you’re like me, there’s no debate that sneakers are hands-down the best shoes to pack and travel in. Plenty are designed for all-day wear, meaning you won’t be dying to take them off as soon as you land, and some are even fashionable, so you can arrive at your destination in both comfort and style. But sneakers are also probably some of the most expensive shoes in your closet, making this Amazon sale a great opportunity to save. One deal you can’t pass up is the versatile Veja Women’s V-10 Sneakers, which are over $30 off. The stylish sneakers are a favorite on travel days when you’ll be walking a lot, but want to be picture-ready. If you’re looking for something a little sportier, you can grab the Brooks Ghost 16 Neutral Running Shoe for 29 percent off. The shoes feature a rocker-like construction that makes for smooth heel-to-toe transitions, meaning your feet can go longer before getting tired. 

• Traveler-loved: Adidas Women’s VL Court 3.0 Sneaker, $60 (originally $75)
• Veja Women’s V-10 Sneakers, $109 (originally $141)
• Arch support: Ryka Women’s Podflow EZ Sneaker, $67 (originally $120)
• Skechers Men’s Summits High Range Sneaker, $60 (originally $87)
• Nike Men’s Promina Walking Shoes, $65 (originally $70)
• Nike Women’s Interact Run Road Running Shoes, $52 (originally $85)
• Cole Haan Men’s Generation Zg Golf Sneaker, $40 (originally $90)
• Rare sale: Brooks Women’s Ghost 16 Neutral Running Shoe, $100 (originally $140)
• New Balance Women’s Fresh Foam 680 V8 Running Shoe, $70 (originally $80)
• On Women’s Cloud 5 Sneakers, $167 (originally $230)
• Lowest price this year: Dr. Scholls Women’s Time Off Sneaker, $44 (originally $110)
• Vivaia Allday Unisex Slip-on Mesh Sneakers, $159 (originally $169)
• Reebok Women’s Club C 85 Vintage Tennis Sneakers, $59 (originally $85)
• Men’s versatile shoe: Cole Haan Men’s Grand Crosscourt Modern Perforated Sneakers, $80 (originally $135)
• Puma Women’s Club 5v5 Sneaker, $50 (originally $70)
• Vionic Women’s Winny Sneaker, $69 (originally $125)
• Hoka lookalike: Allswifit Slip-on Walking/Running Shoes, $56 (originally $65)
• Olukai Kohu Women’s Everyday Sneaker, $58 (originally $100)

Vionic Women’s Winny Sneaker

Vionic shoes are synonymous with comfort, and I can attest that’s completely true. I have a pair of Vionic knee-high boots with a 4-inch heel that I’ll wear as long as I can, and now I plan on stocking my closet with these equally comfy sneakers. You can grab Vionic’s Winny Sneaker for 45 percent off right now. Its leather upper is stylish, and the shoe has a contoured arch and shock-absorbing cushioning that work together to make it incredibly supportive. Its unique build makes it a great option for those who deal with heel pain. 

New Balance Women’s Fresh Foam 680 V8 Running Shoe

Despite their stacked cushioning, which gives them a cloud-like feel, these shoes are incredibly lightweight with a knit upper that improves airflow, making the sneakers really breathable, too. They’re also made with a durable rubber sole that doesn’t wear down easily, so they’re perfect for everyday wear, whether you’re just heading down the street or off to a new country. The New Balance Fresh Foam 680 V8 Running Shoes are on sale for 13 percent off right now, making them the lowest price they’ve been in 30 days. 

Best Hiking Shoes and Boots Deals

Puffer jacket season is coming, and whether that means you plan on hiking through snow-capped hills, or sipping on hot cocoa in a cabin, you should make sure you have on some cute—and functional—shoes to match. Some of Amazon’s current deals on hiking shoes and boots can’t be beat. Take the Nortiv 8 Women’s Hiking Shoes, now just $30, which are waterproof and made with grippy rubber outsoles that can handle all kinds of terrain. If you want a name-brand hiking boot for a steal, you can grab the Keen Women’s Hightrail Hiking Boots for as much as 49 percent off. They’re designed to contour to the natural shape of your foot for a secure and comfy fit. 

Nortiv 8 Women’s Hiking Shoes

Made with a durable rubber outsole that offers solid traction to prevent slips and falls and a waterproof design to keep your feet dry during unexpected weather, the Nortiv 8 hiking shoes will keep your feet comfortable when you hit the trails this fall. Its cushy sole is also made with a ton of arch support to prevent foot fatigue. Snag them for 40 percent off their original price right now. 

Merrell Women’s Moab 3 Mid Waterproof Hiking Boot

The rugged look of these Merrell hiking shoes isn’t just coincidental—they’re actually tough. Its features can keep your feet protected through it all. The gusseted tongue keeps debris from getting into the shoe, its waterproof membrane seals out water without making your feet sweaty, and its lightweight EVA foam midsole offers stability for more secure footing even on uneven terrain. Plus, they’re on sale for almost 40 percent off. 

Best Slip-on Shoes, Loafers, and Flats Deals

For shoes that are versatile in the style department, you can also score deals on flats, loafers, and slip-ons that are perfect for wearing straight from a walking tour out to dinner. If you prioritize packability, you’ll love Vivaia’s Margot 2.0 Women’s Casual Flats, which are currently a rare 15 percent off. The shoes fold in half, becoming compact enough to fit in your personal item or squeeze into a corner of your carry-on. Vivaia is a comfortable footwear brand regularly featured in Travel + Leisure lists, like this one, because its shoes pack a ton of arch support, making them supportive enough for all-day wear without sacrificing style. Those looking for something a little dressier will love the Sam Edelman Michaela Stud Mary Jane Flats, now up to 59 percent off, depending on the color. The shoe’s square-toe design and sleek strap make it one of the more fashionable deals on this list. 

• Rare sale: Allbirds Women’s Tree Breezer Ballet Flats, $70 (originally $100)
• Kizik Vegas Slip-on Sneakers, $80 (originally $129)
• Dr. Scholl’s Women’s Nova Sneaker, $45 (originally $80)
• Ugg lookalike: Inpaksa Women’s Platform Mini Boots, $23 (originally $32)
• Dearfoams Women’s Fuzzy Memory Foam Claire Clogs, $31 (originally $44)
• Cushionaire Weston Hand Woven Ballet Flats, $55 (originally $80)
• Celeb-approved brand: Vivaia Margot 2.0 Women’s Casual Flats, $110 (originally $129)
• All-day comfort: Naturalizer Women’s Karis Loafer, $35 (originally $110)
• LifeStride Women’s Charlie Slip-ons, $60 (originally $100)
• Traveler-approved: Skechers Women’s Go Walk Flex Slip-Ins-Grand Entry Sneaker, $67 (originally $87)
• Sam Edelman Women’s Michaela Stud Mary Jane Flats, $53 (originally $130)
• Oprah-loved brand: Vionic Women’s Uptown Loafer, $64 (originally $130)
• Cushionaire Hana Suede Classic Clog, $50 (originally $80)
• Oofos Oomg Slip-on Recovery Shoe, $100 (originally $140)

Cushionaire Hana Suede Classic Clog

Clogs are a fall shoewear staple, and these suede ones from Cushionaire are designed with a comfort that can’t be beat. The slip-on shoes are made with a contoured cork footbed that molds to your feet, giving you a stable fit you won’t mind standing all day in. You can also adjust the buckle strap for an even better fit. The clog is on sale in several colors, including brown, black, and camel. Just make sure to redeem the coupon to grab it at this special price. 

Kizik Vegas Slip-on Sneakers

Kizik’s unisex Vegas Slip-on Sneakers are built with a collapsible heel, which allows you to easily slip into them quickly. The shoes made T+L’s list of the best walking shoes for travel because they were immediately comfortable with no break-in period required, thanks to their cushy and supportive soles. Despite being so comfy, the shoes are also much more fashionable than other slip-on sneakers. Plus, you can grab them for 38 percent off right now, making them just $80. 

Best Ankle and Knee-high Boots Deals

Winter and fall are the perfect seasons to wear your cutest ankle and knee-high boots. But if what you own feels a little last season, Amazon’s October Prime Day is a great time to refresh your closet because there are so many boots on sale. The Sorel Men’s 1964 Pac Nylon Waterproof Boot is a must-have for you or for anyone on your holiday gift list this year (it’s never too early to start shopping!). Not only is it stylish, but the boot has a Sherpa cuff to keep feet warm in frigid temperatures, and its water-resistant design can handle slush and snow. The calf-high boots are an impressive 61 percent off right now. The LifeStride X-Anita Boot is also a great shoe for colder temps. Its high profile keeps feet cozy, and its fashionable design pairs well with denim, oversized sweaters, and leggings. You can currently shop it for $30 off. 

Lucky Brand Women’s Basel Ankle Bootie

The best deal on this list at 69 percent off is this pair of cute leather booties from Lucky Brand, which you can grab for an amazing $40 (that’s $89 off the regular price). They’re made with a cushy footbed that makes them comfortable to wear for hours on end, and zippered closures on both sides, so you never have to force your feet into the shoes. You can pair these with a flannel for the perfect fall- (or holiday!) inspired fit.

Dearfoams Fireside Shearling Perth Foldover Boot

You can’t let Amazon Prime Big Deal Days pass by without stocking up on a fresh pair of warm, cozy booties to get through the winter in. These Dearfoams foldover boots are made with temperature-regulating Australian sheepskin. The soft and fluffy material is breathable and naturally adjusts to your body temperature, so your feet never overheat even if you wear these during warmer temps. Down 30 percent, you can grab these booties for $97 right now. 

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