The Best Men’s Boots for Fall 2021
The Best Boots
for Fall
From rugged chukkas to waterproof rain boots, we’ve got something for every situation you might find yourself in this season.
It’s finally fall, which means it’s time to swap your sneakers for something a little more rugged and reliable. We rounded up a few of our favorite options, from classic desert boots and chukkas, to chelsea boots and rain boots.
Astorflex Greenflex Chukka Boots
The family behind Astorflex has been making shoes by hand in Italy for more than six generations. The Greenflex is a classic desert boot - the kind favored by everyone from Steve McQueen to soldiers fighting on the hot sands of Northern Africa during WWII.
Built with premium suede leather and a rugged rubber outsole, these everyday chukka boots provide a little more structure than their better known big brother, the Clarks Desert Boot.
XTRATUF Deck Boots
The unofficial boot of the 49th state, XTRATUF earns every letter of their name. XTRATUF Deck Boots are 100% waterproof and made from moisture-wicking neoprene — designed from the ground up for life at sea.
Each pair is constructed with a chevron sole that has a vice-like grip, even on the slick decks of commercial fishing vessels. At the end of the day, when you grab hold of the thick pull tabs and kick off your boots, your socks are sure to be bone dry.
Red Wing Heritage Rover Boots
The right pair of Red Wing Heritage boots are worth their weight in gold. Hang around a construction site for long enough and you’ll lose count of how many you see.
First released in 1952 to outfit mill workers, The Rover takes Red Wing’s world-class materials and shapes them into a sleeker, more modern silhouette — all without sacrificing an ounce of durability. If you could only have one pair of boots to last you a lifetime, it’s these.
Red Wing Weekender Chukka
Red Wing Heritage, manufacturer of high-quality leather work boots boasting more than 100 years of experience, departs from their traditional occupation-specific designs with a casual off-the-clock shoe. Made with Red Wing’s traditional construction methods and materials, the Weekender Chukka is flexible, lightweight and exceptionally tough.
Astorflex Bitflex Chelsea Boots
The Bitflex Chelsea Boot is one of the best kept secrets in men’s footwear. Handmade in Northern Italy by a family that's been making boots for six generations, these slip-on boots are eco-friendly, handsome as hell, and represent the best value on the market. The smooth leather and stylish shape land right in the sweet spot between more utilitarian Chelsea-style boots and the pointy-toed ones of the Jagger persuasion. They instantly elevate any outfit and are comfortable enough to take you through the whole day and into the night.
Blundstone Classic 550
Born on the rugged Australian island of Tasmania, Blundstone makes work boots that can go through hell, but feel like heaven on your feet. Starting with the simple, iconic elastic-sided silhouette, Blundstone adds a premium leather upper with soft leather lining on the interior, a durable, grippy outsole, and a soft footbed with advanced Poron XRD cushioning. Slip into something a little more comfortable.
The All-Weather Duckboot
The AWD has the classic good looks of a duckboot, the all-terrain versatility and durability of a Range Rover, and comfort that rivals your favorite sneakers, all wrapped up in a waterproof package you can rely on everywhere. And trust us, you’re bound to wear them everywhere.