The Elsinore Jacket from Iron & Resin is something that could have easily been passed down from Steve McQueen or Paul Newman. It just has that handsome, leading man quality about it. They've even given it a Japanese wool blanket liner for an extra layer of warmth and its cut slim with stretchy side panels for an enhanced fit. The jacket is tumbled and pre-washed for that broken-in look and the shoulders are detailed quilted shoulder pads.

$650, ironandresin.com