My son is 2½ years old. He loves to wear dresses and twirly skirts like his big sister. If my daughter walks out the door in a dress, he instantly wants to do the same. This is fine by me.

Meet Rachel, 36. She shares how her son’s love for dresses opened her eyes to the meaning of parenting. "I never thought twice about my son's clothes—until he started choosing dresses.

My 2-year-old son started preschool in January, and the daily drop-off routine has become a refreshing source of style inspiration. More and more, I want to model all of my outfits after the way ...