Rambler's Way, $115
Everyone's familiar with the Henley shirt—the long-sleeved pullover that looks a bit like the top half of a union suit. The underwear connotation makes sense. For decades, the only place you would've seen one was under the work shirt of a ranch hand. But now, they're showing up everywhere, from J.Crew's broken-in style and Gap's nautical take to a vintage-inspired wool version with contrast stitching from Rambler's Way. The ultimate all-season shirt, they're ideal for layering in the winter and then come spring thaw, undoing the buttons and pushing up the sleeves. And while it's casual, that doesn't mean you can't wear one with your favorite blazer. But it's made for layering so pull a henley over a T-shirt and under a flannel shirt with a denim jacket, or a pea coat if it's really cold.