A Ton of Cole Haan, Sperry, and Other Men's Shoes Are on Sale for Prime Day 2024—Shop These 10 ASAP

With Amazon Prime Day 2024 now underway, many are stocking up on the power tools, fitness equipment, and camping gear they've been waiting to go on sale. Those looking for men's shoes have plenty to pick from this year, with dozens of thousands of pairs of Amazon's bestselling men's sneakers, sandals, and boots now on sale for up to 50% (or more, if you know where to look) during the summer savings event.

On Amazon, you'll find that the major footwear brands you know and love, like Cole Haan, Sperry, and Saucony, have already reduced prices on classics like the Grand Crosscourt sneaker, the A/O 2-Eye boat shoe, and the Guide 16 running shoe. But there are also plenty of brands you may have never heard of before with deals on comfortable flip-flops and even hiking boots at jaw-dropping prices. After Men's Journal browsed through Amazon's Prime Day deals on men's shoes, we found 10 that are worth an immediate add-to-cart.

Asics Gel-Kayano 30 in Black/Sheet Rock, From $100 (was $160) on Amazon

The Asics Gel-Kayano 30 might be the most comfortable running shoe on sale during  Prime Day 2024. These are loaded with cushion and are a great option for anybody going for short daily runs or simply getting their 10,000 steps in. They're also very supportive and suitable for both neutral foot types as well as those who overpronate. Make sure to pick up your size quickly, because last year, a bunch of these sold out.

What Shoppers Are Saying: "I have gone through multiple running shoes, inserts, and even got the legend of running shoes itself—Hoka—but nothing seemed to help with my semi-flat feet...I got these as a last resort and I am very glad I did. The comfort is great and the shoe gives just enough stability and bounce for running outside."

Keen Newport H2 Closed Toe Water Sandal in Black/Steel Grey, From $88 (was $125) on Amazon

Whether you're heading out on the boat or want something breezy when touring while on vacation, look to Keen's Newport sandal to keep you comfortable. This sandal has an ergonomic footbed, a water-resistant and washable synthetic upper, and a ton of traction thanks to an outsole that looks more like an expensive car tire. It's also backed by over 23,000 five-star ratings from shoppers who've left glowing reviews. For $88, you'll be hard-pressed to find a better rugged sandal than this one.

What Shoppers Are Saying: "Been wearing this model for over 10 years and they never disappoint. Comfortable right out of the box every time. I wear them almost daily and they last me roughly two years, which is longer than most other shoes I wear. Not bad for a sandal."

Clarks Bushacre 2 Chukka Boot in Beeswax, From $60 (was $100) on Amazon

If you're looking to score a great deal on men's boots for fall, Clarks has one of the best during the Prime Day sale. The Bushacre Chukka Boot is a classic and one that's virtually trend-proof, though they've been very on-trend for the past several years. This pair has Clarks' signature two-eye lacing, but it's packed with comfort thanks to a cushioned insole. It's a smart pick if you're looking for something between dressy and casual.

What Shoppers Are Saying: "These shoes are everything I hoped they would be and then some. Great looking, comfortable, fit great, great quality, great price!"

Cole Haan Grand Crosscourt Modern Perforated Sneaker in Black, From $58 (was $128) on Amazon

This classic perforated sneaker from Cole Haan is the perfect anytime summer shoe. It's wonderfully understated with a simple color scheme and falls somewhere between the preppy style of an Adidas Stan Smith and the sporty nature of a Nike Dunk. Feel confident wearing it with everything from shorts to khaki pants for all kinds of events this season, regardless of the formality.

What Shoppers Are Saying: "These were field-tested on a two-week vacation out of the box. They were comfortable and required zero break-in. Look great and fit true-to-size."

KuaiLu Yoga Mat Leather Flip-Flops in Khaki, $12 (was $20) on Amazon

These simple flip-flops from KuaiLu are Amazon's No. 1 bestselling men's sandals, and they're just $12 in this neutral brown color. They're loaded with arch support, so you won't just be walking on flat rubber all day, and there's truly something for everybody with over 25 different colors to pick from in sizes 7 to 16. While many are on sale, it's this particular khaki color that's the best deal.

What Shoppers Are Saying: "Better than expected…They’re of good quality and true to fit. The bottom reduces slips and is tough enough to comfortably walk around outside, even on some rocks."

Sperry Authentic Original 2-Eye Boat Shoe in Classic Brown, From $63 (was $110) on Amazon

Sperry's A/O 2-Eye boat shoe is a perennial Prime Day purchase for many, and select colors are on sale once again this year. Prices seem to vary based on the combination of color and size, which is normal for many shoe styles on Amazon, but most are still between 20% and 25% off and a better price than you'll find at Zappos.

What Shoppers Are Saying: "I cannot count the pairs of Sperry topsiders I have bought throughout the years—they're the best summer shoes. You can wear them without socks without your feet getting sweaty or slimy. They wear like iron."

Florsheim Rubano Wingtip Oxford in Cognac, From $80 (was $130) on Amazon

The Florsheim Rubano in Cognac is a near-perfect dress shoe—trust me, I have them. It's very forgiving in the width and always looks fantastic when paired with a pair of trousers for work or even a pair of jeans for that perfect smart-casual aesthetic. If you need a wide, I recommend buying it because, while they do stretch, they still come to a slight point at the forefoot.

What Shoppers Are Saying: "Fantastically comfortable…Great looking shoe and all-day comfort. Can’t beat the price. More comfortable than my Cole Haans that were more than double the price."

Saucony Guide 16 Sneaker in Agave/Marigold, From $69 (was $140) on Amazon

The Saucony Guide is a beloved style that's sought-after for its pillowy cushion and slightly structured support for those who need it. It's super lightweight and breathable, which is perfect for summer running, and provides a smooth ride and comfortable underfoot experience, whether walking, jogging, or doing HIIT workouts.

What Shoppers Are Saying: "The last running shoe you will ever need…This shoe has the perfect amount of stability. It's not a maximal shoe but it's not a minimal shoe. It will do great on 3-mile runs and 5ks but it also won't let you down for marathon training or on race day."

Nortiv 8 Armadillo Ankle High Waterproof Hiking Boots in Taupe Suede, $43 (was $90) on Amazon

Nortiv 8's Armadillo hiking boots are some of the most underrated on the market, but then again, they're Amazon's No. 1 bestselling pair for men. These boots might not have the household name recognition that Merrell or Keen do, but they offer everything you'd want from a great boot—waterproofing, a hard-wearing upper, good tread, and toe protection.

What Shoppers Are Saying: "I have about 60 to 70 miles in these hiking boots so far. They're about on par with my Keens, but are much better than my Merrells. Took about 5 to 6 miles for them to 'form.' Did a 9-mile hike the other day and my feet felt great."

Hey Dude Wally Ascend Woven Slip-On Casual Shoes in Abyss, From $44 (was $65) on Amazon

Hey Dude's Wally slip-on shoes were a smash hit during last year's Prime Day sale, and they figure to be a big part of it this year as well. This pair is now under $50 and is the perfect color for everything from weekend outfits to your next vacation go-to. Make sure to grab one soon, though, because they tend to sell out fast.

What Shoppers Are Saying: "You can never go wrong with Hey Dudes! Comfortable, breathable, light and they look good with any outfit. Dress them up or down."