Label: Richard Chai
Richard Chai has serious style, but you already know this. His clothes are perfect for guys who just want to look cool without looking like they toiled for hours in front of the mirror. That's what's so great about his designs: they're pragmatic but still attractive, they look like things you could just throw on, and once you do, you remember why you bought it in the first place. His line has brought him collaborations with brands like Penguin, and their easygoing casual looks will soon be reinterpreted into classic American gear, as Chai was recently named the creative director of Filson.