It’s a familiar exchange to many women: “I love your dress.” “Thanks, it has pockets!” So coveted is the spacious inset pouch in womenswear that when they exist, they are likely to attract attention.

A reader wonders why pockets in women’s wear remain “small and useless” — when they’re included at all. The answer is tangled up with a host of social issues, our critic writes. By Vanessa Friedman ...