Why we like it: Crafted from 100 percent lambswool, the Fjällräven Byron Hat Thin is a luxe option for cold-weather comfort.

In 2025, the $500 winter hat isn't just plausible—it's a market reality. What began as standard-issue gear for merchant marines—known then as a "watch cap" or "sailor cap" for long nights at ...

Tanya Frazee, a coach from Girls on the Run Georgia, highly recommends Trailheads’s winter hats. Her favorite is the brand’s ...