It’s hard arguing against a fashion staple that has been around for nearly 60 years. Given its recent resurgence, Clark’s Desert Boot has survived decades of fashion onslaught due to its unparalleled simplicity and comfort. After owning a pair for over a year, my boots are just as comfortable as the day that I bought them (thanks to its superb crepe rubber sole). They come in a variety of colors, however I’m quite partial to the light sand tan. $95 at Clarks.