Woolrich Woolen Mills Roark Vest in Gold, $195
When buzzed-about designer Mark McNairy took the reins of designing the Woolrich Woolen Mills collection, people were cised about what kinds of clothing he would make. He's known for his interesting mash-ups of American staples, and it shows in this vest. A Frankenstein of the traditional waistcoat and winter vest, he combines nylon material with a cotton lining and polyester insulation, resulting in a unique yet wearable piece. You don't have to rock it under a blazer, shake things up by throwing a denim chore jacket or olive M-65 over it.