CLARK’S DESERT BOOTS
An affordable menswear fall staple if there ever was one, Clark’s Desert Boots have been the definitive chukka since their iconic silhouette debuted back in 1950. The Desert Boot is available in a plethora of color options in leather or suede and is always paired with the comfortable signature crepe rubber sole. Personally, we’re partial to the timeless Beeswax leather colorway.
DR. MARTENS VEGAN 1460 FELIX
The 1460 is the original Doc Marten silhouette, recognized for its yellow stitching, eight eyelets, grooved sides, and air-cushioned sole. But while this iteration of the 1460 may have a classic look, its construction is all modern as it’s been crafted with 100% vegan materials, resulting in a more sustainable and eco-friendly boot.
L.L.BEAN THE ORIGINAL L.L.BEAN BOOT
The original duck boots were invented by L.L.Bean founder… uh, L.L. Bean… back in 1912, and the brand has been making them by hand in Maine ever since. The boots fuse a full-grain leather upper to a waterproof rubber base via a triple-stitch method that workers spend half-a-year learning how to master before getting the chance to do so, and the end result is one seriously watertight icon.
SOREL MADSON II MOC
Sorel is one of the best in the biz when it comes to outdoor boots, and while many of their options lean into snowier weather, these waterproof suede-trimmed moc-toes are perfect for fall. The Madson II combines waterproof usability with sneaker-like comfort and classic casual moc-toe looks, creating a hybrid boot that you can wear all autumn long.
JOHNSTON & MURPHY XC FLEX CODY CAP TOE
American heritage brand Johnston & Murphy has been cranking out quality footwear since 1850, and the XC Flex line is the company’s latest innovation. The tech combines J&M’s signature heritage styling with athletic shoe-style cushioning and moisture-wicking, meaning this handsome brogue feels more like a basketball shoe than a dress boot.
THURSDAY BOOT COMPANY CAPTAIN
While Thursday Boot Company is not over a century old like some brands on this list — the brand began less than a decade ago — they have quickly established themselves as a major player in the space thanks to their commitment to high-quality materials and honest pricing. The Captain is one of their standout models, as it’s a versatile dress-casual boot with a supple glove leather-lined interior and a studded rubber outsole.
BLUNDSTONE CLASSIC 550 CHELSEA BOOTS
Blundstone’s original 550 Chelsea Boots are an unquestioned iconic design with their distinctive double pull-tabs, and now Blundstone has made this icon better than ever. The shoes, while always comfortable, are now even more plush with Poron XRD foam inserts in the heel-strike zone, an EVA classic comfort footbed, and a polyurethane cushioned midsole.
If you like the idea of a Chelsea Boot but find Blundstones to be a bit too casual and utilitarian for your tastes, then have a look at Astorflex’s Bitflex. This luxe Chelsea boot has been handmade in Italy by the same family for six generations, and it’s crafted from soft European suede and features a cloud-like 100% natural crepe rubber sole and an ergonomic footbed.
DANNER LOGGER 917 GTX
Danner is one of the first names in hiking boots, but the 89-year-old Oregon-based brand makes some of the best non-hiking boots, too. The ever-popular 917 is one such offering. Inspired by old logging boots, this modern casual silhouette gets an upgrade here with a GORE-TEX breathable waterproof liner, a Vibram SPE rubberized EVA midsole, and an exclusive-to-Danner Vibram 917 outsole featuring XS Trek rubber compound.
SANDERS & SANDERS HI TOP CHUKKA BOOT
If it’s retro cosmopolitan style you’re after, then put English heritage brand Sanders & Sanders on your radar. Their suede Hi Top Chukka, also known as the “Playboy,” was a favorite of Steve McQueen in the 1960s, who wore them both on and off-screen. The shoes also appeared on the feet of James Bond in Spectre, and if you play your cards right, you can add yourself to this comfy and stylish boot’s list of notable wearers.
RED WING HERITAGE CLASSIC MOC 875
Red Wing’s Classic Moc is about as classic as boots get. Since its 1952 debut, this American-made boot has been a favorite among everyone from factory workers to farmers to fashionistas. The boot’s combination of a moc toe and Traction Tred rubber outsole provide its recognizable silhouette, while its Puritan triple stitching and Goodyear welt construction make it one of the most durable boots you’ll ever own.
TAFT THE JACK BOOT
With the slogan “Boots for the Bold,” it should be pretty clear that Taft’s boots aren’t for everyone. Their styles are idiosyncratic and sometimes in-your-face, but no one can accuse them of being poor quality. The Jack Boot is one of the 8-year-old brand’s trademark models, and it definitely offers some unique styling that you won’t find anywhere else thanks to its raw wool upper that’s complemented by a calfskin toe cap, heel counter, and pull tab.
WOLVERINE ORIGINAL 1000 MILE BOOT
If you plan on putting your fall boots through Hell and back, then Wolverines ought to be on your feet. The Michigan-based American heritage brand’s 1,000 Mile Boots are an absolute legend and are arguably the best-known work boot there is. Made by hand in the USA from the original 1914 pattern, this iteration of the icon features a premium suede upper from Charles F. Stead, Goodyear welt construction, and a cork midsole.
TO BOOT NEW YORK BURKETT
If the average dress boot is a bit too finicky and delicate for your lifestyle, then give the Burkett from To Boot New York a go. The beautiful cognac leather upper and cap toe silhouette say dress boot, but the metal eyelets and Blake-stitched lugged rubber outsole scream rugged casual wear. However you end up wearing the Burkett, you’re going to look fantastic.
CROCKETT & JONES CONISTON
If you truly need a real dress boot this fall, then you quite literally cannot do any better than Crockett & Jones. The English brand has been crafting some of the highest quality footwear in the world since 1879, and the Coniston is just one in a long line of showstopping boots. These high derby dress boots were inspired by classic officer boots and feature Goodyear welted construction, an upper made from the finest scotch grain leather, and an authentic Dainite studded rubber outsole.
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