“It’s odd growing up as a teenager when your parents are a lot cooler than you.”

“I think, quite often, what happens in people’s minds is that ambition creates an unobtainable goal so there’s never a feeling of fulfillment,” says British fashion designer Charlie Casely-Hayford. “A lot of people go through life chasing whatever it is that keeps them motivated. If you don’t reflect on your achievements, it’s very hard to move forward in a positive way.”

Perhaps this meditative tendency comes naturally to a man who seems predisposed toward equanimity; or, it could be that his long-term relationship with interior designer Sophie Ashby has introduced in him a more well-rounded attitude. Either way, the 30-year-old, whose eponymous label is designed in partnership with his father, Joe, is careful to temper his personal aspirations with self-examination. In...