Ask Sam letter


To Sam

Is crossdressing okay?

Hey Sam,

So Im writing to you to ask you if you have any advice on how to tell my family that i want to crossdress. I am scared of what they might think as when i told my mum she wasnt encouraging at all in fact the opposite. I would really like some tips,

Thank you,


Ask Sam


Hi there

Cross dressing means wearing clothes and accessories which are often associated with the opposite gender. This might mean wearing a dress if you’re male or a shirt and tie if you’re female. You have the right to choose what you wear and this should always be respected by other people.

It’s okay to express your identity through the clothes you wear and how you look. Clothes don’t really have a gender, but society can put expectations or ‘rules’ on which gender should wear which clothes. Trying to look a certain way to fit can make you unhappy and you might want to try different clothes and styles to find what’s right for you.

Wanting to cross dress isn’t necessarily about your gender identity or sexuality and it doesn’t mean that you’re trans, gay or bisexual. Anyone can prefer wearing clothes their gender wouldn’t often wear or choose to wear gender neutral clothes which don’t have female or male labels automatically attached to them.

Being open with other people about how you want to dress might feel scary when you don’t know how they’ll react. But you might find that people are open minded and are interested in you being happy and doing what’s best for you.

You need to prepare yourself for the people who might not understand or might not want you to look or dress in a way that they see as unusual or different. How you want to dress might not be what your friends or family expect and sometimes it can take time for them to understand. Not everyone will accept what you choose and some people might say things that are hurtful or unkind. You can’t control what other people think but you don’t need to let that stop you doing what feels right for you.

If you decide you feel ready to tell your family, friends or partner about cross dressing it can help to choose a time that they’re not busy and they can listen. Tell them that what you want to say is important to you and that you’re telling them because you want their support. Let them know that you want to experiment with or try out wearing new things, so that you can do it in a safe place at first, like at home. Telling somebody you want to cross dress is different from coming out about your sexuality, but our tips on coming out might give you some ideas on how to tell people.

Remember, being happy with yourself and choosing clothes that feel right for you can help you to build your confidence and self-esteem in the long run. It’s okay to wear whatever you want to.

I hope this advice has helped. You can talk to a counsellor at Childline for more support.

Take care,


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