Whether you’re excited to say goodbye to summer or you’re still hanging on to the last sign of warm weather, lamenting the inevitable change of the seasons, Fall is here. And that means not only shorter days, colder mornings and evenings and a whole new series of opportunities for epic outdoor adventures, but also means its time to ramp up your wardrobe. As the days get slightly colder, you’ll find yourself reaching for a few more layers (one reason that so many people like the season), and begin phasing out not only the brightly-colored shorts and tees, but also those casual white sneakers that match them. In their place, you’ll be reaching for the perfect pair of Fall boots.
No matter what particular style you’re into (rustic mountain man, casual, slightly-formal in the city), there’s a pair of stylish, comfortable, and rugged boots out there for you. Here’s our top 10 picks.
If your fall looks like it’s going to be taking you offroad, into the trail, or you just like a casual, rustic vibe (say, flannel shirt and jeans or chinos), these Timberland White Ledge Hiking Boots will get the job done. They’re inexpensive but attractive, made of a full-grain leather upper with an oiled finish; this leather upper is also waterproof, making these boots perfect for everything from hiking to being caught in a rainstorm. The rubber outsole with multi-directional lugs ensures excellent traction on any surface, and the gusseted tongue helps relieve lace pressure for a super-comfortable boot.
For casual rustic style, you really can’t go wrong with Timberland.
Chelsea boots are a stape of men’s style, worn by everyone from rockstars (The Beatles, for example) to Steve Mcqueen. This gorgeous Chelsea boot is handmade in Italy by a family with six generations of bootmaking experience. In other words, these boots rock. They’re assembled out of a super-soft suede European leather and paired with a 100% natural crepe rubber sole that is firm enough to withstand everyday use but light and comfortable enough for wearing everyday, everywhere. The ergonomic footbed and undyed leather lining make sure of that.
We already like Taylor Stitch for their abundance of stylish, functional apparel, from high-end leather moto jackets to comfortable Sherpa pullovers. Their footwear offerings are just as good, it seems; the Taylor Stitch Ranch Boot is a slightly-different take on what appears to be a classic Chelsea boot, laceless and slip-on, but this time outfitted for work around the ranch. Handmade in Leon, Mexico, they’ve got a beautiful saddle tan leather upper with Goodyear welt construction, paired with a Vibram inset mini lug sole. In other words, they’re nigh indestructible and ready for use on the slickest of surfaces. Jeans, chinos, denim jackets, field coats – the Ranch boots work with all of them.
Because why not? They’re the original and (sometimes) still the best pair of chukkas out there, and you usually snag a pair for dirt cheap (try Amazon). We like them best in the classic beeswax, but blue suede and sand look solid too. (To be fair, every color looks that good…)
Rugged, classy, traditional – and built to last decades. There’s seriously no other way to describe these incredibly-good looking boots from Thursday Boot Co. The President boots feature an absolutely beautiful tobacco leather upper that we can only imagine will age even more beautifully, paired with a water-resistant Goodyear Welt Construction and rugged, studded rubber outsoles. Add in an Unbreakable Fiberglas shank and anti-microbial shock absorbing insoles, and you ultra-comfortable boots built to last.
Wherever you’re going to wear these shoes, they’ll hold up. And whatever you plan to wear them with, we guarantee they will look incredible. They also come in sandstone and black, but we’re definitely partial to the Rugged look of Tobacco. Really doesn’t get more classic than these bad boys.
These are more in the casual and outdoorsy vein of the Timberland White Ledge and they’re built with Danner’s extreme rugged quality and designed to last. The Mountain Light was many a backpacker’s choice of trusty footwear for decades, and this updated edition does the original justice. Handbuilt from a one-piece leather upper, they’re 100% waterproof, lined with Gore-Tex, while a Vibram Kletterlift outsole lends them serious traction and serious shock-absorption.
Whether you need a pair of boots to rock rain (and maybe some snow) fall, or you need something built for the long-haul on all your late-season backpacking trips, Danner’s got a classic pair that delivers. Pair with flannel and jeans when chilling around the campfire.
Leather is cool, sure, but you really just want something casual and chill for rocking at the party and the city streets. The Eisner Chukka from Ecco are exactly what you’re looking for. Pair with some tapered denim, your favorite tee, and a cool jacket, and you’ve got a super-relaxed outfit for super-chill nights on the town.
A pair of hiking boots that you can rock to the gym too, if you feel like it. The Under Armor Post Canyon Mid have a textile and suede upper for the perfect combination of light weight and strength, and are based around a light EVA midsole. The UA Storm membrane offers waterproof performance without letting your feet suffocate, and the rubber toe cap and heel overlays add durability and scuff-resistance without weighing the shoes down. A high-traction rubber lug outsole seals the deal, ensuring you can wear these boots everywhere from muddy rocks to slick asphalt. Under Armor knows what the perfect combination of athletic style and rugged utility is and designed these boots right at that intersection.
Danner makes more than just hiking boots. The Jack II brogues are the perfect choice for dress boots to pair with a suit or pair of fancy dress pants, built from rich full-grain leather and using Danner’s favorite 971 last. A vintage 270 rubber outsole (named for the number of stitches running around the outside) looks as good as leather, but gives you more grip on wet pavement, and a fiberglass shank adds stiffness and support. They also make use of a very traditional leather midsole, which molds and forms to your feet ever so slightly for extra comfort.
Oh, and before we forget – they look fantastic too, with those brogue perforations and dark coffee finish. When classiness counts, the Jack II should be the shoes you reach for.
We hadn’t heard of Sutro before, but they apparently make some stylish, handmade and premium leather footwear right from their own shop in San Francisco. The Ellington Ciclon are classic, but anything but derivative. They’re based on traditional leather work boots, but are only 5 inches tall, making them a good ankle boot for more casual applications – as does the Moc Toe, which cements the Ellington’s status as a relaxed piece of footwear. The upper is full-grain vegetable treated leather, built on Goodyear Welt Construction with a hand-carved stack leather sole. On top of that leather sole is Sutro’s custom natural leather sole for added flexibility and grip; Vibram on the heel helps with that, too.
The Ellington Ciclon certainly makes for a unique blend of both work and casual style. They’re handmade in San Francisco, so we feel pairing them with vintage American jeans is only appropriate.
Rustic durability is the name of the game with the LL Bean Allagash Chukkas. They look a lot like the legendary Bean boots, but comfier, and designed more for the lodge than the hunting trip. The soft full-grain leather and suede upper is built to withstand anything, and the seams are lock-stitched to ensure they hold up forever. There’s an ergonomically-shaped footbed for comfort, a nylon shank for stiffness and reliable support, as well as a lugged rubber outsole to ensure you’ve got traction on any surface. And did we mention their LL Bean? Enough said. The brand is known for their extremely rugged, durable boots, and the Allagash shouldn’t be any different.
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