The actress apparently wants each of her children to have a unique personality and has allegedly decided that Shiloh should be a tomboy.
A source told Life & Style: "She's been dressing Shiloh in her older brother Maddox's hand-me-downs, including making her wear boys' boxer shorts, for years.
"Angelina has an idea that each child should have a specific personality that she picked out for them practically at birth.
"She's the tomboy."
Shiloh's name is of male Hebrew origin with meanings including "his gift" and "he who is to be sent".
Psychologist and parenting expert Jonathan Alpert commented: "It's normal for a little girl to explore the opposite gender.
"But if a parent is trying to defy a cultural norm at the expense of the child, that's a different story. Parents shouldn't push their agenda via their child."