Where He Went: Filson

Richard Chai's design pedigree earned him a spot designing for Marc Jacobs' namesake line before he branched out on his own in 2005. Known for favoring dark colors while reinterpreting casual menswear staples like flannel shirts and military-inspired outerwear, he even did capsule collections for companies like Target and Penguin. In 2012, his penchant for rugged yet wearable men's clothing netted him a position as creative director for Filson, the American outdoor brand.