Fall outfits take many forms. There’s a certain point, right around the time when the temperatures start dropping, that getting out of town starts to sound like a very good idea. Maybe you’re heading for the hills for some fresh air or simply taking a break from the city before the holiday madness kicks in. Whatever the excuse, there’s something to be said about spending a couple of days somewhere where there are more trees than people. (Whatever gets you out the door, really.)
And while a little fresh air is reason enough to get out of town, we’d argue that getting dressed for it is half the fun. Think chunky knits, substantial outerwear, sturdy boots, and all those rich, tactile fabrics that make dressing for the colder months so appealing. Of course, a weekend away can take you from a slow morning at the cabin to a muddy trail to a nice dinner in town, sometimes all in the same day. So we’ve put together a few fall outfits for dressing the part.
5 Unimpeachable Fall Menswear Upgrades
Hunkered Down in the Cabin
If you’ve gone through the trouble of renting a cozy hideaway for the weekend, you might as well make the most of doing nothing. This territory is prime for the softest of flannels and, say, a shawl-collar cardigan from Elder Statesman, the reigning kinds of impossibly good knitwear. And pajamas at noon? Perfectly acceptable, provided they’re Derek Rose’s brushed plaid bottoms. Add Charvet’s suede slippers and a pair of marled wool socks, because cabin floors are notoriously unforgiving to bare feet.
Kapital
Ivy Rainbowy Happy Heel Cotton and Hemp-Blend
Charvet
Suede Slippers
Derek Rose
Kelburn Straight-Leg Checked Brushed Cotton-Flannel Pyjama Trousers
Paul Smith
Wool Henley T-Shirt
CDLP
Camp-Collar Lyocell Pyjama Shirt
The Elder Statesman
Shawl-Collar Cashmere Cardigan
Hoofing It on the Trails
You’re here for some fresh air and a nice view, and chances are, you’ve got a well-marked trail to work with, so you don’t gotta go overboard. A thrashed sweatshirt will do just fine, but a pair of trail-ready pants from Portal will give you more freedom than your usual jeans. Trail or not, there’s a case to be made for a proper pair of hikers from Diemme, the Italian brand that’s been making exceptionally handsome footwear in the foothills of the Dolomites for decades. Better still, they’re the kind of boots you’ll wanna wear after you’ve made it back to civilization.
Our Legacy
Orbit Hooded Twill Bomber Jacket
Canada Goose
Lodge Quilted Shell Down Gilet
Sease
Explorer Wool-Blend Zip-Up Ski Mid-Layer
Portal
Traka Straight-Leg Recycled-Shell Trousers
Aimé Leon Dore
Shearling-Trimmed Suede Trapper Cap
Diemme
Roccia Vet Suede Hiking Boots
Crunching Leaves Around Town
Arguably the best part of any weekend getaway to the country is the chance to indulge in a little small-town living. Poking around antique shops, finding a good cup of coffee, or settling in for an early dinner. You might be the only person in town wearing a shearling-collared coat from Yves Salomon, or a pair of cords from The Row, but that ain’t a reason to leave either at home. And do you need to wear a pair of rugged Chelsea boots to browse the stacks at the local bookshop? Probably not. But damn if you won’t look like a well-dressed son of a gun doing it.
Yves Salomon
Shearling-Lined Suede Coat
Auralee
Striped Cotton and Silk-Blend Shirt
Drake's
Brushed Shetland Wool Sweater
R.M. Williams
Gardener Waxed-Suede Chelsea Boots
The Row
Fred Slim-Fit Straight-Leg Cotton-Corduroy Trousers
Lemaire
