Because of their nearly endless variety, there is no single answer for "how do you wear boots?" Where a chukka boot could be worn casually with shorts thanks to its slightly lower height, a chelsea boot -- also a more casual style -- has a higher silhouette and therefore calls for long trousers.

As you style your boots, keep in mind that they tend to be a casual option. With some notable exceptions designed for suiting (such as balmoral or button boot styles), boots are best worn with denim or chinos, or at most tailored separates.