The Ultimate Trail-to-Town Wardrobe for Fall


Shoulder season is the best. Out here in the Rockies, where I live, it’s that glorious downtime between hectic summer crowds and frantic ski-season hoards, when trailheads are mostly empty, aspen trees are in full golden glory, and the local brewpub has a lot more room. From leaf-peeping jaunts around alpine lakes to squeezing in one last epic mountain bike ride, there’s plenty to do. But the weather’s also changing and unpredictable. You’ll need a wardrobe that can keep up whether you’re in the backcountry or the back room at the bar, which these double-duty clothes can do.

The North Face Men’s Slim-Fit Motion Pants ($75)

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(Courtesy The North Face)

The Motion Pants are a do-everything classic. The gusseted crotch and articulated knees help you move through mountains, and the slim fit and on-point styling keep you from looking like too much of a hiker when you’re out to dinner.

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Women’s Smartloft 60 Jacket ($180)

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(Courtesy Smartwool)

Wool is an incredible insulating layer when the temperature drops and keeps you warm even if it gets wet. It’s also stink-free, meaning you won’t draw the wrong kind of attention when you head into town for a post-ride pint.

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Outdoor Research Men’s Prologue Refuge Jacket ($199)

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(Courtesy Outdoor Research)

This jacket has a workwear vibe that’s way more fashionable than your typical down puffy. Plus, you get the benefit of waxed canvas on top for weather resistance and a lower half that’s stuffed with Outdoor Research’s new, extremely breathable VerticalX insulation.

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Pladra Men’s Elli Olympic Brown Flannel ($119)

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(Courtesy Pladra)

A nice flannel is a must. It’s as good-looking as it is capable. Pladra makes awesome shirts for men and women that are bombproof, made in the United States, and backed by a lifetime guarantee for anything that fails during normal use. The slimmer cut and fun prints on the cuffs and inside the collar are nice touches that’ll help you stand out from the sea of plaid.

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Teva Arrowood Lux Waterproof ($140)

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(Courtesy Teva)

It’s hard to find shoes with enough grip and protection for the trail that won’t make you look like a Boy Scout around town. Enter the Teva Arrowood Lux Waterproof. These things are insanely comfortable, thanks to a proprietary foam in the sole that’s lightweight and durable. The fully waterproof leather upper means they’re ready to tackle whatever the trail throws at them.

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Fits Casual Crew Socks ($22)

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(Courtesy FITS)

Fits makes my favorite wool socks. They last longer than any others I’ve worn, and true to their name, the fit is incredible. For an all-around travel sock, go with the Casual Crew. They’re a bit thinner than the brand’s hiking-specific styles, but they still have some cushion and are made with a wool blend, so your feet won’t stink after a day or two of exploring. Plus, the hip patterns make it easy to dress up.

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Mission Workshop Radian Travel Pack ($585)

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(Courtesy Mission Workshop)

Yes, this is an expensive backpack, but it’s also damn near perfect. The front panel zips all the way open so it can be packed like a normal suitcase. It has compartments for your laptop, iPad, and plenty of other gadgets. The rolltop offers quick access to your gear, and the shoulder straps tuck away so you can check it on a plane. On top of all that, this pack has an adjustable internal frame to let you dial in the fit and is made from super-durable, water-resistant materials that stand up to plenty of abuse on the trail while looking stylish enough for the big city and mountain town alike.

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