The
J.Press
Bobcap

It's hand-crafted in Scotland from quality British wool, looks like something Michael Bastian might wear (or make) and is surprisingly affordable. In other words, there's nothing bad to say about J.Press's classic striped bobcap. The old school stocking cap might be the only piece of cold weather headgear you could wear to work without looking like you just got dropped off a ski lift. After all, who better to create a handsome, functional and durable winter hat than a century-old Connecticut-based company with a respected "if it ain't broke, don't fix it" philosophy?

$36 ($28.80 with code PSDEC11), at J.Press