My Winter Wardrobe (Part Two)

After avoiding hats for many years and suffering through many cold winters as a result, I've finally decided to get serious about finding one that works for me. Reader "Pame9" recently reminded me of Eugenia Kim's chic and expansive collection (thanks Pame!) and now I'm a little obsessed with this houndstooth one. It satisfies all my criteria: I wanted a style that, aside from offering warmth, doesn't fit too snugly (to avoid hat head) and isn't too thick or woolly a knit (to minimize static cling). The checkered fabric, leather trim, and pared-down shape amount to a cool-but-refined take on an outdoorsy trapper—it's definitely cozy but still satisfyingly sleek, which was just what I wanted (but didn't think was possible) from a hat.