It's impossible to think of Y2K fashion without remembering graphic tees, and their quippy, self-referential slogans. Britney Spears’s “Dump Him,” and Paris Hilton’s “Stop Being Desperate” tops remain ...

Graphic tees can be very, very good. They can also be gaudy or outdated. The trick is to find one right that feels modern but with a nod to the retro. Anything too new-feeling ages quickly—but too ...