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.

• The Boots: Season Three Ansel Hiking Boots, $345 — You assuredly recognize these rugged boots from other posts on the best men’s boots on the blog, right? Think of them as functional-yet-refined hiking boots that are made for so much more than hiking.
• The Henley: Buck Mason Field Spec Cotton Surplus Henley, $68 — The best #OOTD for fall starts with one of the best men’s henleys … like this Buck Mason henley, for instance.
• The Rugged Shirt: Filson Field Flannel Shirt, $98 — My friends, consider it official. With rugged construction and a standout color, the Filson Field Flannel Shirt is one of the best flannel shirts for fall, period. Make it yours ASAP.
• The Jacket: Todd Snyder Made-in-New York Field Jacket, $428 — To give this outfit rugged functionality and serious style, layer up with one of the best men’s field jackets from New York City’s Todd Snyder. One of the coolest men’s jackets out there.
• The Denim: Mott and Bow Slim Oliver Jeans, $108 — Consider this outfit versatile and dependable for fall days in and out of town. Classic slim blue jeans from Mott and Bow can go anywhere, from the winery to a brewery and back (wear a mask!).
• The Watch: Ollech & Wajs Pilot Watch, $1,245 — Go ahead and invest in one of the best men’s adventure watches right this second, and be prepared to never miss a beat: This Ollech & Wajs watch is designed to mimic a cockpit control panel.
• The Belt: Billykirk No. 354 Braided Natural Leather Belt, $44.99 — The best men’s accessories, like the best leather belt, are always a crucial part of any #OOTD (as you well know), so make sure you’ve got the best with this braided leather belt from Billykirk, folks.
• The Socks: American Trench Merino Activity Socks, $19.50 — Finding the best men’s socks is crucial when it comes to the proper pairing with your hiking boots, ehh? Start with American Trench Merino Activity Socks, folks.
• The Headphones: Master & Dynamic MW65 Noise-Cancelling Headphones, $499 — For evening listening on your back deck at home in your den or on a weekend getaway, get some of the best Bluetooth headphones on the market.

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!