In these fraught times, it’s tempting to daydream of the ’80s. And while it’s easy to view them a little too favorably through nostalgia’s skewed lens, some things really were spectacular back then.

Whether you’re a casual hiker, a seasoned backpacker, a thru-hiker chasing the triple crown or a world traveler, you’ve likely faced a classic footwear dilemma: hiking shoes vs. hiking boots. It’s a ...