The Trailhead Classic

Published on May 28, 2025

The Trailhead Classic is your no-fuss look for outdoor adventures and those easygoing weekends when you’re aiming for relaxed but effortlessly sharp. Rugged enough to handle the trail, yet stylish enough to blend in when you’re grabbing a post-hike pint, it’s that rare mix of utility and cool we all secretly (or not so secretly) want in our wardrobe. Think hard-wearing details paired with a look that says, “I didn’t try too hard…but yeah, I nailed it.