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

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)
(Hannah McCaughey)

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)

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

(Hannah McCaughey)


Daily Fit plaid shirt by Chip Foster ($198)

(Hannah McCaughey)


Mount Pierce waterproof jacket by Timberland ($198).

(Hannah McCaughey)


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

(Hannah McCaughey)


Mercury sweater by Ministry of Supply ($168).

(Hannah McCaughey)

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