Notice what your child does. Does he reach for pink, dresses, and frilly shirts? Does he like to cross-dress often, or just on occasion? Does he say that he is being like a girl, or is he just a boy who just likes pink?
Reassure yourself. For some parents or caregivers, this can be surprising information. Your child can cross-dress and still be happy. You are still a good parent. Your child is not the only one who behaves this way, and it is going to be okay. Try reading LGBT+ and feminist literature, particularly stories about people who grew up being a little different. These can help you understand how to be supportive, and can assuage any worries.
Read about transgender children and cross-dressing. Some children crossdress because they think it's fun. Other children are transgender, and feel happier when they can act like the gender they are at heart. A transgender child will need to transition to their true gender, while a child who cross-dresses for fun will be perfectly happy having some dresses and skirts available. Either way, your child needs love and support for being who they are.
Let your child experiment. This sends the message that it is okay to be himself, and that you support him no matter what. Given free reign, your child will try different things and settle on what he feels comfortable with. When you are shopping for clothes, let him wander between blue and pink sections if he wants too. Let him dress up in old clothes or costumes. (Make it clear that if he is borrowing clothes from a sister, he needs to ask permission first!)
Talk to him. Use a positive tone to indicate that you aren't upset with him, and you want to understand him. Ask him about what he likes, and tell him a little bit about cross-dressing and gender presentation if he's curious. Ask why he likes to dress in "girl clothes." (This can help you determine whether he is transgender or just cross-dressing, and you will understand him better.) Try having an honest conversation about gender norms in society and how these are often demonstrated through clothing choices. Even though many people adhere to gendered clothing choices, this does not mean that one has to adhere to this and it is okay to dress the way he wants! Fashion is a great vehicle for self-expression, so as long as it is a safe environment, clothing choices can be explored and enjoyed.
Be honest about school and bullying. If you have concerns about how your child will be received by his peers, talk to him about it. He can weigh in his own mind how important cross-dressing is to him, and whether he wants to go in public this way or not. This will teach your child that he is capable of making his own decisions, even when life is unfair. "Boys can get teased for dressing like girls. It isn't fair or right, but it does happen. Whether you want to have painted nails in school or not is your decision, and I support you either way."
Try engaging in some "girly" activities together. If you are painting your nails, offer to paint his too. Have a tea party together, or dress up in tutus and dance. This sends the message that you love him, and that it's okay to be feminine. Showing respect for girly things will help him learn to show respect for girls.
Defend him in front of others. If other adults say cruel things about you or him, make it clear that you are not okay with this. Your child has a right to be himself, and you are being a good parent by letting him make his own decisions. If your child is upset, reassure him that he's okay. They're mean. If someone is a bully, that is their fault (and not his). Imagine if your child saw someone being bullied.You would want him to stand up for them. Be a role model to your child and stand up for him.
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