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Overlooking Harpers Ferry, a small town in Western Virginia.
Overlooking Harpers Ferry, a small town in Western Virginia. (Photo: ablokhin/iStock)

The Ultimate Trail-to-Town Wardrobe for Fall

Stylish, do-it-all shirts, jackets, packs, and shoes that go from the backcountry to the bar

Published: 
Overlooking Harpers Ferry, a small town in Western Virginia.
(Photo: ablokhin/iStock)

New perk: Easily find new routes and hidden gems, upcoming running events, and more near you. Your weekly Local Running Newsletter has everything you need to lace up! .

Shoulder season is the best. Out here in the Rockies, where I live, it鈥檚 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鈥檚 plenty to do. But the weather鈥檚 also changing and unpredictable. You鈥檒l need a wardrobe that can keep up whether you鈥檙e in the backcountry or the back room at the bar, which these double-duty clothes can do.

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

(Courtesy The North Face)

The 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鈥檙e out to dinner.


Women鈥檚 Smartloft 60 Jacket ($180)

(Courtesy Smartwool)

is an incredible insulating layer when the temperature drops and keeps you warm even if it gets wet. It鈥檚 also stink-free, meaning you won鈥檛 draw the wrong kind of attention when you head into town for a post-ride pint.


Outdoor Research Men鈥檚 Prologue Refuge Jacket ($199)

(Courtesy Outdoor Research)

has a workwear vibe that鈥檚 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鈥檚 stuffed with Outdoor Research鈥檚 new, extremely breathable VerticalX insulation.


Pladra Men鈥檚 Elli Olympic Brown Flannel ($119)

(Courtesy Pladra)

A is a must. It鈥檚 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鈥檒l help you stand out from the sea of plaid.


Teva Arrowood Lux Waterproof ($140)

(Courtesy Teva)

It鈥檚 hard to find shoes with enough grip and protection for the trail that won鈥檛 make you look like a Boy Scout around town. Enter the . These things are insanely comfortable, thanks to a proprietary foam in the sole that鈥檚 lightweight and durable. The fully waterproof leather upper means they鈥檙e ready to tackle whatever the trail throws at them.


Fits Casual Crew Socks ($22)

(Courtesy FITS)

Fits makes my favorite wool socks. They last longer than any others I鈥檝e worn, and true to their name, the fit is incredible. For an all-around travel sock, go with the . They鈥檙e a bit thinner than the brand鈥檚 hiking-specific styles, but they still have some cushion and are made with a wool blend, so your feet won鈥檛 stink after a day or two of exploring. Plus, the hip patterns make it easy to dress up.


Mission Workshop聽Radian Travel Pack ($585)

(Courtesy Mission Workshop)

Yes, this is an expensive backpack, but it鈥檚 also . 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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