Sam Roloff isn’t your typical player in Portland’s fashion scene. He’s not a designer, a shop owner or even a clotheshorse, but his dreamy fashion paintings just plopped him onto the style radar all the same. Roloff (whose name might sound familiar with his brother Matt Roloff’s show Little People, Big World) was raised in the Bay area and studied fine art at the San Francisco Art Institute in the early 90s. After that, his life reads a little like a Keroua...

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