Best Early Amazon October Prime Day Comfy Shoe Deals

Where does the time go? It feels like just yesterday we were preparing our closets for sunny days at the beach and backyard barbecues, and now, we’re already entering the second week of October. With chillier days and holiday travel plans fast approaching, it’s a good idea to take stock of your comfy fall shoe rotation (or lack thereof) now, rather than later. Luckily, you can fill any holes in your collection while saving money thanks to Amazon’s Prime Big Deal Days, a sitewide members-exclusive sales event that will run from October 8 to October 9. 

Even though the Prime Day event has yet to come, we’re already seeing major discounts on sneakers, slip-ons, boots, and loafers from top brands like New Balance, Adidas, Columbia, and more across the site. To help you get a head start on Amazon’s best shoe deals happening this week, we’ve compiled a list of 16 sales you won’t want to miss out on, like these suede leather loafers, nearly 50 percent off, or these under-$100 Sorel winter boots. 

Hurry, though: With such steep deals, we can’t be certain these styles will be in stock for much longer. 

New Balance Women’s Fresh Foam 680 V8 Running Shoe

These Fresh Foam 680 V8 running shoes are lightweight, supportive, and cute enough to style with jeans or a matching lounge set. On sale for $53, these New Balance sneakers are built with an ultra-cushioned midsole and a knit upper that’s vented to keep feet cool and sweat-free. One five-star reviewer said they love this specific shoe so much that they’ve purchased them three times so far — and “will certainly buy them again.”

Columbia Women’s Newton Ridge Plus Hiking Boots 

Have a fall hike on your horizon? Skip the gnarly break-in period of other hiking boots and grab a pair of these ultra-comfy Newton Ridge Plus hiking boots instead. I recently purchased these last minute for a trip to Costa Rica, and much like this five-star reviewer, I found these Columbia boots to be comfortable right out of the box. I had no time to break them in prior to the trip, but as it turns out, I didn’t need to, thanks in part to the padded interior and cushiony collar. You can get a pair for yourself this Prime Day for up to 47 percent off. 

Vilocy Men’s Casual Tennis Sneaker

The best travel shoes are versatile enough to suit multiple activities. These Vilocy casual tennis shoes fit the bill: They’re supportive and comfortable enough to walk on hours-long city tours but are handsome enough to pair well with slacks for dinner. Featuring a breathable knit upper, a flexible EVA outsole, and a high-rebound, removable cushioned insole, these lightweight lace-up sneakers deserve a spot in your carry-on — and are 23 percent off for Prime Day. 

Osslue Women’s Suede Leather Loafer

When it comes to building a solid fall shoe rotation, you can’t go wrong with a pair of leather loafers. Their classic silhouettes stand the test of time and are a reliable option for work, travel, and beyond. This suede leather pair from Osslue, almost 50 percent off, hasflexible, non-slip rubber outsoles and can be folded to fit squarely in a small bag. They havememory foam insoles and a podiatrist-designed footbed that adds stability and support to your step. 

Skechers Women’s Bobs B Cute Shoe 

We love Skechers for their easy, reliable walking shoes; not only are these Bobs B Cute shoes versatile enough to pair with dresses, shorts, and jeans alike, but they’re also comfortable enough for long travel days. Constructed with 100 percent canvas uppers, memory foam comfort insoles, and flexible traction outsoles, these machine-washable everyday sneakers have earned an eye-popping 31,000 five-star ratings for their effortless style and comfort. The best part? They’re on sale for just $30 this Prime Day.

Brooks Women’s Adrenaline GTS 22 Running Shoe

Footwear brand Brooks is perhaps best known for their collection of high quality running shoes. These GTS 22 sneakers are usually $140, but you can grab a pair for yourself for just $85 during Prime Day. They have the brand’s trademarked GuardRail technology built in, which prevents excessive movement, keeping your feet in their natural stride. They also have cushioned midsoles and have received the American Podiatry Medical Association (APMA) Seal of Acceptance for promoting good foot health. 

Merrell Men’s Moab 3 Hiking Shoe

For a limited time, you can score these hiking shoes from outdoor footwear authority Merrell on sale for as low as $86. These all-terrain, all-purpose hiking shoes have ultra-rugged Vibram rubber outsoles that provide traction on slippery terrain. They are also built with a contoured footbed, air cushion shock-absorbing midsoles, and added support in the ankle for extra security on uneven surfaces. Previously $170, these top-rated Merrell shoes are nearly 50 percent off this Prime Day. 

Naturalizer Women’s Vivienne Ballet Flat

With the “balletcore” style trend still going strong, we’ve been digging for options that are cute and comfortable. Ballet flats tend to lack necessary support for longer periods of wear, but these Naturalizer Vivienne flats are stacked with comfort-forward features, like a cushioned insole, non-slip rubber outsoles, and a padded collar around the heel that prevents blisters. They also come in wide size options, for those who struggle with the narrow silhouettes of other ballet flats. So far, these supportive ballet flats have earned over 1,400 five-star ratings, with one reviewer sharing that from day one, they’ve been able to wear these all day with no problems.

Sorel Women’s Tivoli IV Tall Waterproof Boot

With fall in full swing — and winter closely approaching — it’s not a bad idea to stock up on cozy high-quality boots while they’re on sale for Prime Day. Specifically, we have these Sorel Tivoli IV boots on our wishlists. They’re usually $165, but right now, you can get a pair of these fluffy waterproof boots for less than $100. Constructed with waterproof suede and leather uppers, a grippy, molded rubber outsole, and fuzzy microfleece lining, these lace-up boots provide the traction and support you need for snowy days (not to mention, they’re absolutely adorable). 

Ryka Women’s Devotion Plus 2 Walking Shoe

These supportive Ryka Devotion Plus 2 walking shoes have colors and sizes running as low as $55 for Prime Day. Originally $100, these Ryka shoes are equipped with an eight-piece rubber sole that provides increased traction on tricky surfaces, a dual-layer cushioned midsole for additional shock absorption, and an anatomical insole built with added heel and arch support. With so many comfort-first features throughout, you can clock in as many steps as you like while keeping your feet happy. 

Tiosebon Women’s Slip-on Walking Shoes 

These super-stretchy knit slip-on shoes have earned nearly 11,000 five-star ratings — and they’re on sale for just $19. They’re ultra-lightweight, meaning they won’t add extra pounds to your carry-on or checked bag, and they’re built with removable memory foam cushioned insoles and a breathable mesh knit upper that stretches to conform to your foot and allows you to take them on and off quickly. 

Asics Men’s Gel-Kayano 30 Running Shoe

These best-selling men’s Gel-Kayano 30 running shoes usually cost $160, but they’re $50 off for Prime Day. They’re built with increased heel bevels for controlled impact, plus sculpted midsoles and enhanced shock-absorbing gel built into the soles. Whether you’re training for a marathon or just need a supportive walking shoe, these premier sneakers are up for the job. 

Lifestride Women’s Margot Loafer

Another pair of loafers we’re eyeing for Prime Day are these sleek Margot slip-ons from Lifestride. On sale for $35, these classic faux leather loafers are built with breathable, cushioned soles, an ultra-flexible outsole for natural foot movement, and extra arch and heel support built into the footbed. Their minimalist design makes them a footwear chameleon of sorts because they’re easy to pair with just about anything in your fall travel wardrobe.

Dream Pairs Women’s High-top Winter Snow Boot

Suede winter boots can be pricey, but these Dream Pairs snow boots are just $40 for Prime Day. Originally $68, these boots have plush faux fur interiors and genuine suede leather uppers to keep your toes toasty on frigid winter evenings. They also have cushioned insoles and non-slip rubber outsoles that provide traction while it’s snowing, raining, or sleeting. Over 3,300 shoppers have given these suede boots a five-star rating for their comfort, warmth, and style.

Puma Women’s Softride Enzo Evo Cross Trainer

Previously $75, these Puma cross trainers are currently on sale for just $38 for Prime Day — that’s almost 50 percent off the original price. These athletic sneakers have a TPU caging around the uppers to provide support and stability, EVA cushioning, and a sock-lined interior for extra comfort. One five-star reviewer shares that they’re stylish, comfortable, and “fit like a glove.”

Adidas Women’s Grand Court 2.0 Tennis Shoe

We love any opportunity to save on brand names we already know and love, hence why we’re eyeing these classic everyday tennis shoes from Adidas, on sale for over 20 percent off. Made with cushioned insoles, a two-layer sockliner, and treaded rubber outsoles, these tennis shoes are great for travel, errands, and leisurely activities of all kinds. Over 2,000 five-star ratings attest to their quality and comfort, with one teacher sharing that they’re a “lifesaver” on long school days, when they usually have to be on their feet for 13 hours. 

Skechers Men’s Delson Camben Slip-on Sneakers

These handsome men’s lifestyle sneakers from Skechers have received over 27,000 five-star ratings with one shopper sharing that they’re the shoes they “needed so badly.” As someone who struggles with severe arthritis, they added that the slip-on functionality and comfort have proved to be spot-on. On sale for as low as $50 this Prime Day, these sneakers have the cushioned memory foam support of other Skechers styles with an elevated, dinner-ready look thanks to leather pull loops on the tongue and heel. 

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.