How to Get Your Parents to Let You Wear Girls Clothes
Getting your parents to let you wear girls' clothes can be difficult if they don't understand your reasons. If you're not sure what your parents will think, ask an indirect question like, “What do you think about boys wearing girls' clothes.” If they respond positively, you can explain why you'd like to try wearing girls' clothes. For example, say you want to see how it feels, or you feel like it expresses your identity better. You might need to come to some compromise, like only wearing girls' clothes after school or not at church or around relatives. It can be tough if your parents say no, but try to remember that they love you and they think they're doing what's best for you. Not being able to wear girls' clothes doesn't change who you are, and you can wear whatever you want when you're a bit older.
Test your parents on what they think. Start by casually asking what your parents think of boys or men who wear traditionally female clothing as a way to test how they'll react to your own desire to do so. If you see boys or men in girls' clothes on TV or in a movie, point them out to your parents to ask about what they think. Or reference popular transgender women in the media like Laverne Cox or Caitlyn Jenner, especially if you also identify as trans and are thinking about discussing this with your parents. Explain why you want to dress like a girl. Tell your parents the reasons behind your desire to dress in girls' clothing. Be specific about how dressing in this way does or would make you feel, how you benefit from it, or what occasion you want to wear this clothing for. If you don't know why you want to do it, just explain that you feel the need to experiment right now. Let your parents know that clothing is an important way to express yourself and feel confident in your own body. You can point out to your parents that dressing as a different gender than the one you were born as can have all kinds of positive effects, like being able to access a different side or yourself, understand and relate to others better, and even see things you've never noticed before, like your resemblance to a family member or features of your body that you love. Perhaps you only want to dress in girls' clothing for a certain occasion or event. Explain the need or desire to dress in girls' clothing for a play, another performance, or a dance. You can point out that males have been dressing as females on stage for centuries! Discuss your identity. Talk with your parents about what gender you feel you identify with, as this may or may not be tied with your desire to dress in clothing associated with a different gender. Maybe you feel more like a girl sometimes, all the time, or you still feel like a boy but just enjoy the way that girls' clothes look and feel. “Coming out” as trans doesn't have to be a big deal, and you can do it in whatever way makes you feel comfortable. Tell your parents, tell everybody, or tell just your closest friends for now and until you feel comfortable revealing it to more people. You may not identify as trans at all, and be perfectly happy with the body and traits of your life as a boy, but just want to dress in girls' clothing, and that is perfectly normal and worth discussing with your parents. Maybe you feel you identify with being a boy at some times, and a girl at other times, or you don't particularly feel like you fit into either gender! This is perfectly okay too, and you can discuss it with your parents in terms of “gender-queer” or “gender-neutral” if you wish. Break down negative stereotypes. Be prepared to respond to any negative or untrue stereotypes surrounding boys and men dressing as girls or women. You can start by explaining that nothing negative or wrong has “made” you have this desire or identity, and that it is not just “a phase.” Even if it is something you don't do forever, tell your parents to take you seriously. Tell your parents that cross-dressing is more common and normal than they might believe. You can tell them that one conservative estimate says at least 2 to 5% of all adult males dress in female clothing. Explain the unbalanced or unfair situation of girls and women being able to wear clothing that was once considered more traditionally masculine, like jeans, t-shirts, and blazers, and it is seen as normal. But when boys and men attempt to dress in more traditionally feminine clothing like dresses and skirts, it is viewed with much more negativity and seen as “weird” or “wrong.” Your discussion about gender identity or cross-dressing doesn't need to be a discussion about your sexual identity or preference for who you're attracted to, and the two issues do not have anything to do with each other, despite many stereotypes. Calmly but firmly explain this difference to your parents. Remind them that you are still you. Assure your parents if they are having any doubts that your desire to dress in different clothing doesn't change who you are and all the other aspects of yourself that your parents know and are familiar with. Revealing information about your desires to dress as or identify with another gender can come as a shock, a surprise, or just something your parents wish you had told them sooner. You can explain that it's not something you want to keep from them and that you just wanted to find the right way to bring it up and explain it. Ask for their support. Tell your parents that you would really like their acceptance of your decision and feelings, their permission to buy the clothes, or anything else you need from them. Express that you want them to be a part of your life and let them know what's going on. You can say, “I really want your support on what I wear and how I feel about it. This is something that's really important to me right now, and I want you to be involved. Will you help me buy the clothes I want to wear?” Ask your parents for advice they might have for telling friends, teachers, or other important people in your life and how to get their support and acceptance, too. Agree to wear girls' clothes at certain times. If your parents are hesitant about how you want to dress and revealing it to other people, discuss and agree on certain places or occasions you can wear girls' clothing. Find a compromise with your parents, like being able to wear girls' clothes after school but not at school or church. Or decide on special occasions that you can wear female clothes for. Your parents may just need to get used to your new wardrobe in small amounts before they let you wear it all the time, so be patient and agree to let them set some limits at first. Compromise on the type of clothes you can wear. Come to an agreement about the clothing your parents will feel comfortable with you wearing. Try more androgynous (gender-neutral) clothing or mixing boys' and girls' clothes together in the same outfit to ease them into the idea of dressing in more girls' clothes. Try asking for or buying boys' jeans and tops in a slimmer and tighter fit for a more feminine look. Or add girls' accessories or a few key clothing items to a typical boys' outfit. Take them shopping with you. Invite your parents to come with you to the mall or stores where you'd like to buy girls' clothing. Offer to let them help you make decisions and be involved in the whole process. If they won't go to the store with you, show them pictures of what you want to buy or the kind of outfit you might like to wear to get their approval beforehand. You might even ask a parent who identifies or dresses as female if you can borrow some of their clothes or get tips on dressing from them. Being more involved in your decision or transition may help them to become more accepting of it. Discuss makeup and accessories. If you want to add makeup, jewelry, and other typically feminine accessories, discuss these with your parents, too. Talk about what they're okay with you buying and wearing. Come up with compromises for these things, too. Maybe your parents will allow you to wear just makeup and not girls' clothes yet. Or you can agree with them on how much makeup you wear and when you can wear it. Understand their reasoning. Ask your parents for their reasons if they say no to your desire to cross-dress or they express disapproval of your identity or lifestyle. Seek to understand their viewpoint and concerns so you can gauge whether you can convince them over time, or need to seek help or guidance from others. Some parents may have strict religious views that prevent them from easily accepting or allowing cross-dressing. Try talking to someone of their faith who might be understanding of your situation, and have them talk to your parents. If your parents think you are too young to make this decision for yourself, think you don't know what you want, or simply don't want you cross-dressing under their roof, note that it is expected for you to abide by their wishes as long as you are under 18 and a dependent of your parents. Try to understand that it might be difficult for your parents to understand something they've never experienced or don't know much about, but give them time to get used to the idea that you are the same person they know and love even if you dress in girls' clothing or come out as trans. Determine your level of safety. Carefully weigh the risks of dressing in girls' clothing without parent permission, or otherwise disobeying them. You should do what makes you comfortable and happy, but without running the risk of verbal, mental, or physical harm if possible. If your parents are reluctant to accept what you've told them and won't allow you to buy girls' clothes, but don't show signs of verbal or physical abuse or consequences if you disobey them, consider buying the clothes yourself and changing into them once you get to school, or other times when your parents aren't around. If your parents show a lot of anger and hostility, strictly forbid you from buying girls' clothes or living a certain lifestyle, and threaten serious consequences of verbal or physical abuse if you disobey them, do not go against them. Seek help from a friend, teacher, or other adult right away. Reach out to others. Talk to a friend, friends' parents, teacher, guidance counselor, therapist, or other trusted person if you are having trouble talking to your parents or if you feel unable or unsafe to live as yourself in your home. If you are trans and want to talk to another trans person who knows exactly what you're going through and how to help, dial (877) 565-8860 from anywhere in the U.S. to reach the Trans Lifeline. If you need help or have questions regarding cross-dressing and gender or sexual identity, call or chat online with a peer counselor at GLBT National Help Center. Stay strong and be true to yourself. Don't let your parents' disapproval or other negative reactions to the way you dress or identify cause you to suppress or deny your feelings and wishes. This can cause severe mental and emotional disturbance. Be true to yourself and defend your choices as healthy, normal expressions of who you are. 
Test your parents on what they think. Explain why you want to dress like a girl. Discuss your identity. Break down negative stereotypes. Remind them that you are still you. Ask for their support. Agree to wear girls' clothes at certain times. Compromise on the type of clothes you can wear. Take them shopping with you. Discuss makeup and accessories. Understand their reasoning. Determine your level of safety. Reach out to others. Stay strong and be true to yourself. 