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Fall, or boot season, as it’s known in the men’s fashion world, is one of the most fulfilling times of the year. There’s a certain magic that comes with a good pair of men’s boots, but when you can get them for a bargain, the magic increases tenfold. Right now, the Amazon Prime Big Deal Days are lush with men’s boots for every guy in any situation, whether they’re for a job site, for staying warm, or just for looking cool.
With brands like Clarks, Thorogood, and Keen each offering some of their bestsellers at a great price during October’s Prime Day, things can get overwhelming very quickly. And because the sale only runs from October 10 to 11, 2023 12am PT, it’s almost like there isn’t enough time to consider all of the options.
But after Men’s Journal shopped through the boot deals on Amazon, we found that the three top categories available: fashion boots, work boots, and outdoor boots for things like hiking and snow. To help you save time sifting through the boot deals on Amazon during the 48-hour sale, these are the 15 to look at first.
Best Fashion Boot Deals During October 2023’s Prime Day
The Vostey Causal Oxford Boots are a fantastic bargain boot for men who live in areas prone to rain or snow because they’re built with a rubber sole and are water resistant. It’s a great-looking fashion boot in a classic lace-up style that pairs well with a seasonal denim-clad outfit.
What Customers Say: Aside from raving about the affordable price, many customers note the great aesthetics of this Vostey boot, describing it as edgy, versatile, and borderline Western. One customer even bought them to wear at a Renaissance festival and said they fit in perfectly. Some have said they run a little narrow, so for wider-foot fellas, it’s worth considering a half-size up.
[$31 (was $60); amazon.com]
Clarks is the originator of the desert boot—a chukka-style boot with a crepe sole that was originally intended for use in the desert. Today, they’ve become a menswear staple to be worn with jeans, chinos, and really anything. The Bushacre, a newer desert boot style from Clarks, in the “Sand Waxy Suede” colorway is one of the nicest looking.
What Customers Say: Some say they prefer these to the original Clarks desert boot because of the thicker suede upper and sole but note to pay attention to the sizing, which can run a bit large. One customer added to their review, saying after a year of wearing the boots to work almost every day, they “could not be happier.”
[$59 (was $110); amazon.com]
The Rockport Storm Surge is a good waterproof boot for men who commute to work thanks to its lug sole and seam-sealed construction. During the late fall and winter months, even the shortest of walks to work can be hell with bad footwear. Thankfully, Rockport has added a padded collar and shock-absorbing tech in the heel for added comfort to complement the weatherproofing.
What Customers Say: Customers seem to gravitate toward buying this boot either multiple times or in multiple colors because of how well it’s performed both as a fashion boot and as a work boot. Many express their delight with the quality waterproofing with one customer even giving the edge to this Rockport boot over their Danners.
[From $61 (was $135); amazon.com]
A suede Chelsea boot is the icing on the cake of fall menswear and Bruno Marc, one of Amazon’s bestselling men’s shoe brands, delivers another great deal with its take on the popular style. This boot is an easy-on, easy-off daily driver that’ll look great with just about anything, regardless of what shade you pick.
What Customers Say: Of the 11,000 ratings, most agree that it’s a great product for the price, which is insanely affordable. Sizing recommendations are all over the place with some saying to go a half-size up and others a half-size down. We say if you have wide feet, definitely order a half-size up, but if you have narrow feet, order a half-size down.
[$42 (was $56); amazon.com]
These chocolate brown boots from Dockorio feature an inside zip for easy access, a lug sole, and a handsome wingtip detail across the front. Available in three colors, this style is exactly what a fall boot should look like, and they’re perfect for rocking a few times a week.
What Customers Say: Although these have fewer total ratings than other boots, reviewers note how surprised they’ve been by how comfortable these boots are. One customer said they might even buy a second pair because of how much they look like an exponentially more expensive pair of Allen Edmonds boots.
[$79 (was $98); amazon.com]
Best Work Boot Deals During October 2023’s Prime Day
The Rockrooster 7-inch steel-toe men’s work boots feature an easy-access side-panel zip alongside core slip-resistant, static-dissipative, and abrasion-proof designs. They’re compliant with ASTM F2413-11I/75 C/75 regulations and the brand recommends them for use by mechanics, welders, warehouse workers, and more.
What Customers Say: With nearly 1,400 perfect ratings, this style gets applauded for its long-lasting comfort beyond the one-year mark, which many found surprising given the price. One customer, who shared a photo at day 500, claims they’re the best work boots he’s ever bought, even after wearing Redwings.
[$96 (was $140); amazon.com]
Made in the US, these work boots from the ever-popular Thorogood are 20% off—reason enough to get another pair or your first. The steel toe in these boots is compliant with the ASTM F2413 I/C impact and compression EH standards for electrical hazards and the F3445 slip-resistant standards.
What Customers Say: The large majority of the 1,500-plus ratings are five-star, with customers comparing these boots to or giving them the edge over Redwing styles and noting the minimal break-in time. One customer who works in the automotive industry posted a side-by-side of his old boots with the new ones and said how impressed he is with the beating his boots take on a daily basis.
[$204 (was $255); amazon.com]
Wolverine’s 6-inch Overpass work boot has a composite toe and is waterproof, making it a great option for jobs that come with unexpected conditions. The Ortholite insole helps reduce the need for third-party orthotics but it’s removable if you choose to use one. They’re ASTM F2413-11 M I/75 C/75 EH compliant.
What Customers Say: This boot has garnered over 10,500 ratings with most of them being five-star. Anybody from construction superintendents to cold storage workers has said they fit great and offer long-lasting comfort, and many have said they’ll make it to around the one-year mark if you’re really hitting them hard every day. One customer lauded them for their ability to remain comfortable in different environments ranging in temperature from 33 to 105 degrees Fahrenheit.
[$117 (was $180); amazon.com]
A real hardcore-looking boot, this logger from Georgia Boot is a taller, genuine leather lace-up with a thick oil-resistant lug sole. It’s as classic as logger boots get and comes with nearly 100 years of quality reassurance and a one-year warranty.
What Customers Say: Of the 1,600-plus customers who have worn this boot from rocky forests to manholes, many talk about being able to work in them for over 10 hours a day. Shoppers, including this customer who is a mason, also recommend mink oil to keep off substances like mortar.
[$136 (was $181); amazon.com]
Sureway’s Chelsea-style work boot comes in both a soft-toe and composite-toe in black and brown, depending on your needs and preference, and is built on a Goodyear welt. It meets the ASTM F2413-18 EH standard and is also waterproof and heat resistant. For wides, the brand recommends going up a half size.
What Customers Say: Auto mechanics seem to really enjoy these as do people dissatisfied with the Redback brand of Chelsea work boots and anybody looking to get away from laces. One customer who works for “the big brown delivery truck” brand, said they actually thought they were buying a Rockrooster boot, ended up with this instead, and were very pleasantly surprised at how well they worked out for daily routes.
[$70 (was $87); amazon.com]
Best Outdoor Boot Deals During October 2023’s Prime Day
A solid hiking boot choice, the Targhee III is the third iteration of one of Keen’s most popular options for men. Varying in material, its internal membrane keeps these boots waterproof while a thick, textured rubber outsole fights back against any kind of terrain.
What Customers Say: Many customers have shared their journeys of comfort, having various foot shapes and arch needs, in these hiking boots. They’re being used across many state and national parks, but overall, the tone seems to be that they’re high-quality and generous in width. Somebody actually ran them under the tub faucet to test the waterproofing—it worked.
[From $69 (was $165); amazon.com]
Another Nortiv 8 boot to watch is the Armadillo II hiking boot. It’s the best value hiking boot you can find on Amazon, and that’s only solidified with the amount of perfect ratings it continues to get. Available in a variety of materials, it’s waterproof, features a nice rubber toe bumper, and has a decent tread on the outsole as well.
What Customers Say: Customers agree that these boots are well-made, especially given the low price. They also say they run pretty true to size as long as you exercise the wide options should you need one. One customer said she got them for her boyfriend as a work boot and they’ve held up nicely even at his demanding job outdoors.
[$41 (was $51); amazon.com]
It’s that time of year again—gotta start thinking about snow boots. For those expecting heavy snowfalls, this boot from Aleader is the best bet. Rated for a crazy sub-40-degree temperature and seam-sealed to stay waterproof, the only thing you’ll need other than these is a snow blower.
What Customers Say: Customers are finding that the cinching feature is helpful to further keep snow out of the top of the boot. While at least one customer has used them to backpack across wintry mountains, it seems like most use them for suburban and city travel, with one customer even comparing the tread to that of a new tire.
[From $52 (was $99); amazon.com]
An Amazon bestseller, this Nortiv 8 snow boot is going to end up in many homes this year. A high-traction rubber sole and waterproof materials keep this shoe weather-ready with insulation that has it prepped for temps down to under 25 degrees.
What Customers Say: With so many five-star ratings, these boots are holding down a score of 4.5 overall. Customers agree that their feet stay warm and dry—the main point of a snow boot—and that it doesn’t get much better for this price. They also make a great gift, as outlined by one customer who gave them to her postal working husband who walks about 12 miles per day.
[$48 (was $86); amazon.com]
A more affordable option than the L.L. Bean icon, this duck boot from Aleader is the perfect rain boot to use for urban commutes through the fall, winter, and even into the spring. They feature a waterproof shell and water-resistant upper and have a fleece lining to keep your feet warm in chilly weather.
What Customers Say: Customers are very happy with the warmth these boots provide because cold rain (not snow) can kind of sneak up on you. They’re loving the value for a very affordable price. Wide-footed friends are being asked to size up because they may run a bit narrow. One customer explains the boot well, saying that as a rain boot to wear around town, they’re perfect, but not for hiking or dealing with heavy-duty cold.
[$51 (was $90); amazon.com]
More Can’t-Miss Amazon Prime Day October 2023 Sales:
- 15 Prime Day Deals on Men’s Jackets to Shop ASAP, From Puffers to Denim and Everything Between
- The 15 Best Fitness Deals to Take Advantage of Right Now During Amazon’s October Prime Day
- The 25 Best Amazon Gifts for Men During October’s Prime Day From Brands Like Dewalt, Apple, and Levi’s