"When will you wear wigs?" is funny because it sounds oddly formal, slightly dramatic, and deeply specific. It is also a real question many first-time wig wearers ask themselves.
The meme layer
The phrase works online because it turns a normal beauty choice into a strange interrogation. Like many wig memes, it plays with transformation and surprise.
The real answer
You wear wigs when they solve a problem or create joy: hair loss, protective styling, costume, performance, travel, convenience, or a temporary new identity.
Bottom line
The meme is silly, but the question is useful. Wear wigs when they make your life easier, safer, or more fun.