The "Original Outdoors Company" has been around for over 180 years and has set a standard for the Americana crowd. Woolrich is the brand your grand pappy wore proudly, and now it's got two up-market off-shoots designed to appease even the most fashion forward dudes: Woolrich Woolen Mills, a modern take on the brand's expansive archive designed by Mark McNairy, and the decidedly more European Woolrich John Rich & Bros, which takes familiar staples and gives them an Italian-infused sartorial twist.

Mountain Parka, $169 

Westview Shawl Collar Sweater, $69 

Arctic Trooper Hat, $39