The Best Men’s Heritage Outdoor Apparel for Cool Weather

Shoulder seasons can be cold, miserable times transitioning into different weather. But they can also be the best times of the year. Not too hot. Not too cold. Just right — if you dress for them.

With summer leading into fall and winter, shorter days and cooler weather, it’s time to stoke the fire, stir up a hot toddy, and put on an extra layer inspired by the adventurers and craftsmen of yesterday.

Filson

Filson Full-Zip Hooded Anorak Jacket

Filson Full Zip Hooded Anorak Jacket

While not really a pullover anorak, the Filson Full-Zip Hooded Anorak Jacket gives you plenty of protection from the elements. The lightweight cotton jacket is treated with Superdry, which increases the water and wind resistance. The long cut and hand warmer pockets keep the chill away.

Filson Antique Tin Cloth Jac-Shirt

Filson Antique Tin Cloth Jac-Shirt

The name might allude to a certain Wizard of Oz character but this jacket has plenty of heart. The Filson Antique Tin Cloth Jag-Shirt is made with 10-ounce cotton canvas that has a broken-in feel. It’s inspired by vintage hunting jackets and is very abrasion- and wind-resistant. Stack wood, prep meat, or relax in style — this jacket shirt can do it all.

Obermeyer

Obermeyer Carson Down Vest

Obermeyer Carson Down Vest

When you need a touch of extra warmth but still need plenty of mobility in your arms, it’s time to rip the arms off your jacket … or you could just invest in a vest. The Carson Down Vest from Obermeyer is filled with 550 power duck down. The polyester shell is coated with Oberymeyer’s HydroBlock to keep the moisture out. Wear under your favorite ski jacket or as a standalone piece to the après ‘”vestivities.”

Obermeyer Avery Flannel

Obermeyer Avery Flannel

A good flannel is like a good friend, always there ready to go through hard times and good. The quilted lining and hand-warmer pockets add plenty of warmth to this piece. If you’re in the right place, the Avery doubles as a dinner jacket for a night out on the (small) town.

Fjallraven

Fjallraven Greenland Winter Jacket

Fjallraven Greenland Winter Jacket

When the temperature really starts to sink, we need inspiration from ice-covered Greenland. The soft teddy fleece lining and Supreme Microloft insulation of the Fjallraven Greenland Winter Jacket keep the cold out. The outer shell is Fjallraven’s ultra durable G-1000 Eco, a blend of recycled polyester and organic cotton. For more wind and water repellency, apply Greenland Wax. For more breathability and a lighter weight, leave as is.

Fjallraven Vidda Pro Trousers

Fjallraven Vidda Pro Trousers

Already treated with Greenland Wax, the G-1000 fabric in the Vidda Pro Trousers from Fjallraven are going to last through anything you can throw at them. The reinforced, preshaped knees with two-tone color style will stand up to years of abuse. Six pockets hold essentials like a knife and map.

Patagonia

Patagonia Retro Pile Fleece Jacket

Patagonia Retro Pile Fleece Jacket

The full-zip fleece screamed retro even when it first came out and now decades later is still trucking. Patagonia’s famous fleece jackets are a style in and of themselves. This Retro Pile version has a larger pile on the surface than others. The fabric is Bluesign-approved and all the sewing work is Fair Trade-certified.

Patagonia Long-Sleeved Lightweight Fjord Flannel Shirt

Patagonia Fjord Flannel

When a flannel jacket might be overkill, the flannel shirt fits just right. Patagonia’s Fjord Flannel uses premium organic cotton, with no synthetic fertilizers or chemicals. The longer hem keeps the drafts out. The soft yet durable flannel has just the right amount of warmth for cool camp or cabin.

Danner

Danner Mountain 600 Boot

Danner Mountain 600 Boot

Flip-flops aren’t going to cut it once the heat of the summer is gone. The lightweight Mountain 600 boot (or the Enduroweave version) can go anywhere and do anything outside and still look good. With a new lighter SPE midsole and Fuga outsole from Vibram, the Mountain 600 provides plenty of grip and cushion without the weight. The Danner Dry waterpoof liner inside keeps the water out for those (un)lucky enough to live in the Pacific Northwest.

Danner Mountain Pass Boot

Danner Mountain Pass Boot

For more urban style we can step it up a notch to the Danner Mountain Pass. Strong and durable full-grain leather covers the upper part of the boot while waterproof Gore-Tex lines the inside. Danner cut significant weight from the Mountain Light boot by combining the shank, lasting board and midsole to product the Mountain Pass. The brand also went with the Thin version of Vibrams Kletterlift outsole on the bottom. Your legs will thank them for the ounces saved at the end of the day.

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