The best gear of fall, 2027's top travel destinations, Steve McQueen's legendary sweater, and more...

Fall is always quite the ride. It starts in the end-of-summer heat, accelerates as the days shorten, and eventually ends with the crackle of an open fire in the cold November air. Now that we’re at the halfway point, we figured we’d pull over and take stock of the staples that are carrying us through fall. A season that—with all its bends in the road—always asks more of us and our layers. The pieces below answer the call. Flannel and rugby shirts that go from light outerwear to fortifying midlayers. Utility pants that are comfortable at rest and prove their military-inspired mettle once in action. A pair of ropers, a perfect first Western boot—designed to meet the practical demands of 1950s rodeo riders.

The legendary American shirtmaker, Gitman Vintage, is renowned for its buttondowns. Each season, they release limited batches of these shirts, cut and sewn from rare fabrics sourced from around the world. The Brushed Cotton Tweed Shirt is their take on classic fall shirting, made in Tennessee from 7 oz Japanese cotton tweed and brushed for a soft, flannel-like feel.

Relwen founder Jamie Rupp went digging through Midwestern military surplus shops for inspiration, and surfaced with a utilitarian pant for fall. The Drawstring Utility Pant takes everything Jamie loves about vintage military pants—the comfortable cut, tough cotton construction, and spacious patch pockets—and balances it with a clean, structured look. They offer plenty of room for movement, but they’re sharp enough for dinner.

Rugby shirts, adorned with stripes and finished with white contrast collars, are defined by their thick, durable cotton construction. Originally made for the pitch and, later, adopted by early rock climbers for their toughness, the hardwearing spirit of the original rugby shirts was well-preserved by our designers behind Flint and Tinder. The Classic Rugby Shirt is built from soft, sturdy 10.9 oz cotton with underarm eyelets for breathability. Its weight makes it an ideal fall layer, thrown over a tee or bundled under a waxed jacket.

We’ve been mastering the art of gifting for over a decade. For this year’s Holiday Gift Guide, we sourced a soap from one of Japan’s oldest soapmakers. It’s shaped like a Japanese red sea bream, a longstanding symbol of good fortune. Made using traditional wooden molds for Rakugan, an intricate rice flour candy that’s been a Japanese tradition for over 400 years, it features a linen rope for grip and easy hanging next to your sink. Explore more handpicked gifts—from fish soaps to sardine-sized pocket knives—ahead of the holiday scramble.

East Harbour Surplus is one of the newest brands in our shop. They take tried-and-true vintage military and workwear staples and rework them from the ground up in Italy using quality materials. The Kobe Rollneck Sweater is their elevated take on the knits worn by fishermen and mariners since the 19th century. The warm wool blend is soft and keeps its shape, with nautical stripes in perfect colors for the season.

Until the 1950s, rodeo riders wore baseball hats and sneakers because regular cowboy boots and hats were tough to run, jump, and rope in. The original Roper Boot, with its shorter heel and cut, struck a balance. Clean but undeniably Western, our Rhodes Roper Boot nods to that history—and is tough to beat. Legendary bootmakers in León, Mexico, handcraft each pair from top-notch leathers with durable Vibram soles. Resoleable for a lifetime, thanks to the Goodyear welt.

Diversions:

See You Out There

Leaf peeping on New England backroads in a Land Cruiser FJ60.
📸 @chadwick_vt
📍Vermont

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