I have an emotional connection to my Vasque Sundowners, the iconic hiking boots that helped define the category when they were introduced 37 years ago. The all-leather upper, high cuff, Gore-Tex liner, and burly Vibram outsole make the Sundowner both gorgeous and technical. It’s the first pair of hiking boots I coveted and forked over serious money for 20 years ago. I sacrificed my food budget for two months to make that purchase and never regretted the decision. I still have those boots today, and they’re in pretty good shape. They’ve been relegated to work boot duty at this point, but that’s mostly because I didn’t take care of them as well as I should have.