This time of year is somewhat tricky to sort out — you see, it’s not quite the end of summer, it’s not quite early fall … so, what’s a guy to do? That’s where transitional style essentials from some of your favorite brands come into play via today’s #OOTD, which is focused on the best rugged gear for guys. Make no mistake, we’re not going too over-the-top and into flannel shirt + chore pants territory yet (although we’ll get there someday, trust me!). Instead, think of this as a sort of stepping stone from late summer into early fall, with the gear picks to match (kind of like how we talked last month about how to wear your boots for summer).
This look comes through in a similar fashion: All the building blocks are there for you to wear this look up to your cabin or on a socially distanced day trip, just as easily as you can wear it to grab an on-the-go coffee before a park picnic (don’t forget your stylish face mask, folks). The pieces that make up this look are ones you really can wear just about any time, from one of the best men’s T-shirts to a stylish denim shirt and the best men’s bomber jacket (ideal for when things do start to cool off). Naturally, pieces like versatile men’s pants will also be of service. I’ll leave the rest for you to check out below. Go right on ahead and get out there, my friends.
- The Stylish Tee: Forty Five Slub Pocket Tee, $32 — Nothing great starts without the right base layer — like one of the best men’s T-shirts via the Forty Five brand out of Huckberry. They’re changing the way men’s tees are made, for the better.
- The Western Shirt: Todd Snyder Denim Western Shirt, $198 — Todd Snyder has done it again, crafting a stylish denim shirt with a Western-style cut, resulting in — quite simply — one of the coolest shirts for men heading into early fall.
- The Jacket: Buck Mason Oil Cloth Bomber, $225 — Now, you might not quite need a rugged bomber jacket on your shoulders yet, but when you do, it’s hard to go wrong with this classic bomber from Buck Mason, made from outstandingly tough fabric.
- The Pants: Flint and Tinder Tapered 365 Pants, $98 — Mixing rugged and refined with some of the most versatile men’s pants, regardless of season. If you’ve got a more athletic build, these stylish tapered trousers are for you.
- The Boots: Red Wing Heritage Weekender Chelsea Boots, $219 — The right way to step into early fall? Rugged Chelsea boots from Red Wing Heritage, of course. They’re a natural fit with the rest of this #OOTD.
- The Socks: American Trench Mil-Spec Sport Socks (4-Pack), $42.50 — American Trench socks are so stylish and durable, you’re going to want to have more than one pair in your rotation of the best men’s socks. The Mil-Spec Sport Socks are, in fact, some of my favorite socks. Nearly any color would work with this ensemble.
- The Watch: MWC Classic Retro Military Watch, $79 — There’s no doubt this rugged military watch is one of the best watches under $100, right? Right. Get it now via Cool Material.
- The Daily Essential: Filson Ripstop Nylon Pullman Bag, $250 — Give yourself the ability to go just about anywhere with this rugged everyday bag from Filson, featuring tough construction and plenty of space for EDC essentials.
Who’s ready to squeeze in one last summer adventure before fall kicks in? This look can work right now, and then on into the months ahead. How so? You’re starting with the ultimate base, one of the best men’s T-shirts via the Forty Five brand, a versatile layer in its own right that can be worn individually, for starters. Of course, it can also be layered up with a stylish denim shirt from our friends at Todd Snyder. Those two pieces are truly classic men’s style essentials regardless of season, but they work particularly well right now — especially when matched up with a rugged bomber jacket for those breezy, ever-so-slightly chilly nights. Of course, stylish tapered trousers add a nice dimension of versatility and go-anywhere appeal, namely given that they’re coming from the experts at Flint and Tinder.
The rugged appeal and versatile good looks simply don’t stop, though. Rugged Chelsea boots from Red Wing Heritage deliver the goods when you need adventure-ready, tough footwear that also looks stylish and timeless as heck. To provide comfort and classic appeal in equal measure, be sure to pick up at least one pair of the Mil-Spec Sport Socks from American Trench — classic socks with anti-microbial properties are a new must-have. To me, this look just keeps getting better, specifically when you throw on a rugged military watch for dependable, everyday style. And what’s one of the best ways to accent one of the best watches under $100? That’s easy — a rugged everyday bag from Filson ought to do the trick. So, are you feeling geared up and ready to take on whatever’s next? I sure hope so.
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