Our neighbors to the north know a thing or two about winter – and about hats. Handcrafted in Toronto, The Tilley Winter Hat ($95) from Tilley Endurables is as stylish as it is warm. That could mean it ...

Alex Tilley was in his early 40s when he set out to design a classy, durable hat for weekend sailors like himself. The iconic Tilley hat became a Canadian success story, and spawned the Tilley ...