No fashion era is more contentious than the early aughts — and for good reason. The decade is responsible for whale tail thongs, cargo pants, and skirts over pants (bless you, Ashley Tisdale).

A millennial woman has sparked a conversation about a controversial fashion staple of the early 2000s—low-rise jeans. Low-rise jeans, which gained cultural prominence in the late 1990s and early 2000s ...