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In college, singer-songwriter David Berkeley filed field dispatches for Let’s Go: Alaska and spent summers guiding on the Snake and Salmon Rivers, which is where he began coming up with songs. “I wanted to be a travel writer, but I also loved to sing,” he says. “Once I dove in, it was hard to climb back out.” Berkeley, 38, makes his home in Santa Fe but lives out of a suitcase at least two weeks per month, performing everywhere from Wisconsin to the Netherlands. “The folks at Delta check-in know me by name,” he says. His seventh album, Cardboard Boat—along with his second book, The Free Brontosaurus—comes out in September. Photo: Harbor Plain Toe shoes by Sperry ($100)
In college, singer-songwriter filed field dispatches for Let’s Go: Alaska and spent summers guiding on the Snake and Salmon Rivers, which is where he began coming up with songs. “I wanted to be a travel writer, but I also loved to sing,” he says. “Once I dove in, it was hard to climb back out.”

Berkeley, 38, makes his home in Santa Fe but lives out of a suitcase at least two weeks per month, performing everywhere from Wisconsin to the Netherlands. “The folks at Delta check-in know me by name,” he says. His seventh album, Cardboard Boat—along with his second book, The Free Brontosaurus—comes out in September.

Photo: by Sperry ($100) (Photo: Hannah McCaughey)

Ramblin’ Man: How to Dress for Life on the Road

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In college, singer-songwriter David Berkeley filed field dispatches for Let’s Go: Alaska and spent summers guiding on the Snake and Salmon Rivers, which is where he began coming up with songs. “I wanted to be a travel writer, but I also loved to sing,” he says. “Once I dove in, it was hard to climb back out.” Berkeley, 38, makes his home in Santa Fe but lives out of a suitcase at least two weeks per month, performing everywhere from Wisconsin to the Netherlands. “The folks at Delta check-in know me by name,” he says. His seventh album, Cardboard Boat—along with his second book, The Free Brontosaurus—comes out in September. Photo: Harbor Plain Toe shoes by Sperry ($100)
(Photo: Hannah McCaughey)

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In college, singer-songwriter filed field dispatches for Let’s Go: Alaska and spent summers guiding on the Snake and Salmon Rivers, which is where he began coming up with songs. “I wanted to be a travel writer, but I also loved to sing,” he says. “Once I dove in, it was hard to climb back out.”

Berkeley, 38, makes his home in Santa Fe but lives out of a suitcase at least two weeks per month, performing everywhere from Wisconsin to the Netherlands. “The folks at Delta check-in know me by name,” he says. His seventh album, Cardboard Boat—along with his second book, The Free Brontosaurus—comes out in September.

Photo: by Sperry ($100)

($70) and ($65) by Nautica.

Shirt ($70) and pants ($65) by Nautica.
($70) and ($65) by Nautica. (Hannah McCaughey)

by Chip Foster ($198)

Daily Fit plaid shirt by Chip Foster ($198)
by Chip Foster ($198) (Hannah McCaughey)

by Timberland ($198).

Mount Pierce waterproof jacket by Timberland ($198).
by Timberland ($198). (Hannah McCaughey)

by Hugh and Crye ($35); by Combatant Gentlemen ($40); by OluKai ($140); by Fjällräven ($150); David’s own socks

Popover shirt by Hugh and Crye ($35); Slim Straight pants by Combatant Gentlemen ($40); Pahono Mid shoes by OluKai ($140); Övik backpack by Fjällräven ($150); David’s own socks
by Hugh and Crye ($35); by Combatant Gentlemen ($40); by OluKai ($140); by Fjällräven ($150); David’s own socks (Hannah McCaughey)

by Ministry of Supply ($168).

Mercury sweater by Ministry of Supply ($168).
by Ministry of Supply ($168). (Hannah McCaughey)
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Lead Photo: Hannah McCaughey

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