When the weather starts to warm up, footwear gets lighter, softer and a little more relaxed. And that’s just the time when the desert boot shines. With its signature suede upper, simple two-eyelet lacing and lightweight crepe sole, the classic silhouette hits the sweet spot for spring. They’re easygoing enough for weekend wear but polished enough to hold its own with chinos or lightweight tailoring.

Originally designed for British soldiers stationed in North Africa during World War II, the desert boot has remained a staple for decades because the formula simply works. Drake’s Creative Director Michael Hill calls it a tremendously useful shoe. “You can wear them to dinner, you can wear them with a casual suit or on the weekend,” he says. “If you’re traveling and can only take one pair of shoes, take these.” But while the basic design stays the same, the materials, craftsmanship and finishing details can vary widely depending on how much you spend. Below, we break down three standout options—from a reliable classic to a refined investment pair—to help you decide where it makes sense to upgrade.