Style Pick of the Week: Season Three Ultralight Hiking Boots – The Most Comfortable Boots for Fall and Winter

Most comfortable boots for men this fall.

Folks, step right up and step into the most comfortable boots for fall and winter in today’s prime Style Pick of the Week. It’s a late November weekend, after all, and if you still need to upgrade your fall and winter footwear rotation with a selection of the best men’s boots, you could do worse than picking up a pair of the Season Three Ultralight Hiking Boots.

The NYC-based upstart footwear brand focuses on keeping things subtly stylish, retro-minded and supremely comfortable with its selection of the best hiking boots for men (and women), and they’re a personal favorite of your Brooklyn style writer. And in any style situation this fall and winter, comfort and style are the name of the game — Season Three boots deliver both in spades.

Most affordable hiking boots for men.

The even better news is, these stylish men’s boots are now 40 percent off ($237 vs. $395 full-price). In fact, some pairs of the Season Three Ultralight Hiking Boots are as much as 60 percent off. 60 percent off! So, et’s keep this rolling, shall we?

The best boots for fall and winter, stylish as they might be, are no good if they’re not easy to wear, and luckily for all parties involved, the Season Three Ultralight Hiking Boots deliver on that promise. These sleek yet functional boots are made in a family-owned Northern Italy factory, a haven for the best footwear on the planet. The springy comfort of Ortholite insoles combines with durable Vibram outsoles for a unique blend of traction and exceptional wearability with the Season Three Ultralight Hiking Boots, too. That’s not the only these stylish winter boots have going for ’em.

Best winter boots for men.

Crucially, the Season Three Ultralight Hiking Boots come in a range of cool, eye-catching colors, the kind that call to mind retro hiking boots (especially with contrasting laces in the stylish pair of hiking boots as shown above). Better still is the fact that the Season Three Ultralight Hiking Boots check all the right boxes in other key areas of winter style, too: Just dive into the waterproof nubuck leather found on the Season Three Ultralight Hiking Boots as a starting point.

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For good measure, these stylish men’s winter boots also retain other timeless hiking boot touches, like D-ring lacing and metal hardware. And yet, it all sits atop a chunky, super-comfortable Vibram outsole for plenty of grip on slick city streets and slippery terrain. Yes indeed, the Season Three Ultralight Hiking Boots can do just about anything you ask of them in matters of casual style:

The profile on the Season Three Ultralight Hiking Boots is sleek enough to wear with tailored chinos and your favorite peacoat for polished weekend outings. And once again, here’s the kicker: Right now, the Season Three Ultralight Hiking Boots are on sale for 40 percent off. So, you can get your new favorite pair of winter boots for 40 percent off for a limited time — what are you waiting for, right?

#OOTD: How to Wear the Best New Boots for Guys This Fall

Seeing as we’re cruising through fall, there are a couple things that are pretty clear in my mind in terms of men’s style essentials. For starters, you need a pair of the best boots for men on your feet ASAP. What’s more, you need a functional pair of boots that also happen to look great — while also offering what you might call more unique style. And above all else, you need to know how to wear boots this season, especially when the boots in question are the rugged-yet-refined Season Three Ansel Hiking Boots out of New York City. Featuring the cut of a hiking boot but some of the refined touches of your favorite dress boots, you’ll recognize plenty of versatile complementary pieces to help you get ‘out and about (safely) this season.

From a tough field jacket to a rugged men’s henley, the layers on your top half are every bit as “ready for anything” as your new favorite boots. And on your bottom half, you’ll recognize classics like slim dark blue denim and perhaps the best leather belt and the best men’s socks, all compiled with an eye toward helping you navigate the city, head upstate, get out on a day hike and grab a cold beer at an outdoor (socially distanced!) beer tent afterwards. How does that sound? This #OOTD is nothing if not versatile, so you should keep on scrolling to check it out below. When you build from the ground up with a pair of the best boots for men this season, darn near anything is possible.

Pair up versatile hiking boots with casual, rugged classics for fall.

So, that’s it. That’s today’s #OOTD. It’s a versatile combination of both adventure gear — heck, just check out that exceptional Ollech & Wajs Pilot Watch — plus gear picks that can do a bit of everything (naturally, the centerpiece Season Three Ansel Hiking Boots get the job done). The rest of this ensemble works well in or out of town, especially around a backyard bonfire on a crisp fall night. You’re staying warm with one of the best men’s henleys from Buck Mason, and you’re layering up in rugged, classic fashion with the Filson Field Flannel Shirt for timeless fall style — how about that? Classic slim blue jeans from Mott and Bow tie things together in a way that’s just a bit more versatile than technical hiking pants, and the epically cool Todd Snyder Made-in-New York Field Jacket looks great, provides tough functionality and works with anything in your fall wardrobe.

Naturally, your supporting cast is what’s going to set this #OOTD apart, so the best leather belt from Billykirk is a reliable style move. To keep your feet comfortable in style, I’m a huge proponent of the American Trench Merino Activity Socks — and to ease into your evening with some bourbon whiskey in hand, how about switching on some of the best Bluetooth headphones from the good folks at Master & Dynamic? Taken together, this ensemble provides rugged style, performance, durability and some seriously cool style for fall — can it get any better than that? I don’t think so. If you pick up any of these pieces, feel free to let me know on Twitter. Happy fall, my friends!