Crossdresser Heaven

Learn how to cross dress

The first time a man puts on a dress he looks like – a man in a dress. In our minds we picture ourselves as dainty, feminine and gorgeous, but we’re actually a man caught wearing girl’s clothes. Looking good as a woman is a hard thing to do – just ask any lady who has spent an hour doing her hair and makeup!

Learn how to crossdress

Learn how to crossdress

If you’re just looking for some quick tips on what to wear the first time you cross dress then my previous article is the right place for you to start. If you want to look fabulous, and pass as a genetic woman – then read on!

There are seven aspects to looking great and passing as a genetic woman every time:

  1. Wearing clothes that make you look good
  2. Making sure your curves are in the right places
  3. Feminine body movement
  4. Hairstyle that feminizes your face
  5. Natural makeup
  6. A feminine voice
  7. Loving who you are as a woman

Do we want to look like men wearing dresses?

NO! If you’re like me, the image you hold of yourself is as a beautiful movie star, not a guy in drag. The truth is that we can all look and feel beautiful – but it takes some work. Over the next few weeks I’m going to share with you some of the secrets to looking like the woman you see inside – to cross dress for success.

If you’re eager to look fabulous today, I highly recommend the World’s Best Cross Dressing Guide. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation!

Learn how to cross dress

Learn how to cross dress

Before we get started though, I want to share with you the biggest mistake men make when they wear woman’s clothes. This is probably the number one reason why cross dressers fail to pass, and end up looking like a guy in drag instead of a passable woman.

Before I share it with you, think for a moment on how you picture yourself as a woman. Let me guess, high heels, short skirt, dramatic makeup and plunging neck line. Am I right?

The biggest mistake the transgendered make is that:

When men cross dress they try to look like a whore

Not many woman would be caught dead wearing 6″ heels and a mini-skirt that barely covers their panties. Yet cross dressers try to dress like this – they’re dressing as their own fantasy girl. Take a tip from genetic woman – most of the time they are dressing for their girl friend, or to impress other woman. They are trying to out do other woman, not fulfill a man’s sexual fantasy.

Even if you’re lucky enough to have all the other attributes of a woman, if you dress like a whore you will stand out.

In the first lesson (coming next week), I will teach you how to wear clothes that make you look good, so you can cross dress with confidence.

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About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life! She blogs about the transgender journey at Please comment below and tell me what you think!

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  1. 2 Crossdressing Mistakes We All Make | Crossdresser Heaven | September 2, 2010
  1. Priscilla Aguirre says:

    Thanks for the fine advice. Sofisticated, well explained and useful.
    I can´t wait to go in public but have no company. Love to look younger than 60, but…
    I can´t pierce my ears either and love big earrings.
    First time at your website. I´ts fantastic
    Thanks. Keep it up.

    • Vanessa Law says:

      Hey Priscilla, thanks for stopping by, I’m glad you found the website valuable. There are many great clubs all over the country that cater to crossdressers of all ages. I’m staring down at 30 (less than a month to go!), so I guess I can empathize somewhat. I’d love to be 14 and discovering who I was. there are probably things I would have done differently. But I’ve had a blessed journey as who I am, even if I’ve got more wrinkles than I’d like :)

      Hope to see you back soon.


  2. Vanessa Law says:

    Kelly, thanks for the great tips! I might repost these as an article so other folks can see them as well. Very valuable!

  3. Kelly Stevens says:

    You asked for tips on passing as a woman:
    1. Dress your age. If you aren’t a junior, don’t buy your clothing in the juniors department.
    2. Dress appropriately for the situation. A cocktail dress at the mall isn’t optimum. Make up needs to be appropriate.
    3. Crossdressing is an illusion. A genetic woman can go out without any make up and can look a mess but not look like a man. You can do the same as a man and not look like a woman. You need to constantly preserve the illusion and this involves diverting attention away from your flaws and using clothing and most importantly accessories to preserve the illusion. I do not need glasses but found they feminize me so I bought some (in the women’s section of an eyeglass store). wearing men’s glasses simply is not good enough in 99% of the people I know. I wear a hair band, diamond engagement ring, chain bracelet, necklace, earrings that dangle, and red lipstick because many people have critiqued me and said these things feminize me. The red lipstick and nail polish divert the eyes away from other parts of me.
    4. Choose a wig wisely, This may be among the most important things you do. Length, color, style all matter. (If it is too perfect, it will look fake.)
    5. Hair removal is always an issue. You think nothing of spending a great deal of money on clothing and cosmetics so spend some on a quality razor. Consider hair removal on your face if necessary. I had laser hair removal and it was the best thing I ever did. Use the right foundation to cover the beard but shave it off first! covering is not as good as removing. Shave closely and several times.
    6. Apply make up skillfully.
    7. Cover your arms if you need to. My arms are larger than a woman’s so I wear some type of top. This means I never get to wear sexy cocktail gowns and expect to pass but I can usually find something nice with sleeves. Cover your Navy tatoo!
    8. Keep your skirt length appropriate. In fact, keep everything appropriate. Anything that looks out of the ordinary will be noticed and once you are noticed you will not pass. Much of the time if others really noticed me i would not pass yet somehow I pass extremely well. Why? Because I blend in and fly under their radar.
    9. Avoid direct confrontation with anyone and when it i necessary to interface with a waiter, store clerk, etc. be prepared. When i go to the grocery store i know they will inevitably ask me paper or plastic so I am ready and reach for a plastic bag. I know I will be asked cash or credit so I have my cash or credit card in my hand where they can see it before they ask. But if I have to speak, I speak softly and quietly and smile.In a restaurant, point to the menu item as you order. This reduces the need to fully speak in detail.
    10. Choose where you go in public carefully to minimize problems. If you don’t really pass, stay out of the ladies’ room. I go out at any time of the day or night in Times Square and pass but I avoid groups of teenagers like the plague. They will notice and if they notice they will not notice quietly.
    11. Walk like a woman not a caveman.
    12. Relax. If you are afraid, you will walk like you are afraid. Have confidence.
    13. I’ve seen many men who do not prepare themselves to pass. One CD friends is an auto mechanic and he shows up at support group meetings with black grease on his hands.
    14. Eat and drink like a lady. I love beer but more women drink wine so i drink wine. Men stuff their faces. Women are much more, well, feminine in how they eat. Study female behavior so you can emulate it properly. A word about smoking. I personally feel that smoking is one of the easiest means to tell if someone is a CD or a real woman. Few men can smoke like a woman. You think you can, but you can’t.
    15. Carry a mirror and use it. Men don’t need much attention but women need constant attention. Walking from the parking lot to the Mall can result in blown hair. Eating can alter make up. Be prepared.
    16. Smell like a woman.
    17. Pay attention to detail. You may not be into make up and real women don’t need it to look like a woman but it will really help you. Curl your lashes. (No, don’t use artificial lashes). Keep your clothing stylish. No, that man’s coat isn’t going to pass as a woman’s coat. Details! If you have a huge Adam’s Apple, wear turtle necks. Learn to adapt.
    18. We all want to have our own set of 52 DD tits but if you wear 52DD tits you are going to attract attention and you will therefore be noticed.
    19. Be self aware. Know your limitations. Unless you have practiced dancing like a girl you probably won’t do it like a girl.

    I hope these will help you.
    Kelly Stevens

  4. Vanessa Law says:

    Hi Wendy, thanks for writing. It’s tough when those we love don’t accept this part of us, but I’m happy that you’ve taken some time to express yourself as well. Without this I think we die a slow death inside.


  5. Wendy says:


    I have been dressing in female clothes for years and the feeling is fantastic, a nice little black dress, tights, panties, bra, and heels, it is just a pity my wife does not like agree and join in my fun, woman are so lucky in the way they can dress, us men are so bloody drab, I am new to your site and it looks very helpfull will be back.

    Love Wendy

  6. It’s a funny world we live in when you think of it. I am surrounded by very badly dressed WOMEN every single day. I am thinking that you chaps should be giving them tips 😉

    If you see those programs (in the UK) called ‘what to wear and what not wear’ you’ll get an idea!

    I suppose therefore who you emulate is very important. Emulating the women out and about might actually NOT be a great idea.

    Perhaps find a role model celeb who might match you in build ……….ok forget that, these days those women don’t even look like real women!

    Who to model yourself on?

    Somehow somewhere you need to find a female that matches your build, one with good taste in clothes and try to learn her secret.

    I am thinking these resources might be helpful:

    Catalogs for

    plus size women
    tall women
    petite women

    might actually be fairly helpful?

    Meanwhile here’s an important tip ( I shall use this tip on my blog if you don’t mind Vanessa!!)

    If you are tall and you wear a short skirt with panty hose (tights) they tend to creep down at the gusset and so when seated or even standing the pantyhose come down lower at the crotch than the skirt!! This is not attractive on either sex!

    So my advice

    Keep those skirts nearer the knee than the crotch to avoid this ‘crotch hang’ effect.

    Leah x

  7. Anonymous says:

    You wrote, “think for a moment on how you picture yourself as a woman” but….

    I think you’re forgetting that for some people “cross dressing” just means wearing clothes typically associated with the gender opposite to their own. I don’t dress to pass as a woman, I dress because I enjoy wearing women’s clothes. There’s a big difference between dressing in women’s clothes and trying to look like a woman. But they can both be considered ‘cross dressing’.

    You seem to also be overlooking women crossdressing in men’s clothing. One of my partners does that sometimes, but she does it for a more theatrical effect, not a fetish and not to pass as a man.

    It’s too bad that your outlook on crossdressing is so narrowly focused. You seem to have some good advice, but you seem to be assuming that everyone is just like you. And though I don’t know much about this big ‘ol world, I do know that we’re not all alike.

    Kind regards,

  8. Lynn Jones says:

    > Am I right?

    One out of four isn’t bad. :-) You got me on the heels, but my feet look like boats in flatties. While I may wear heels, they’re not that high – not those “FMSs” that people keep for the bedroom.

    For what it’s worth, I think you can do a lot worse that taking note of women your age are wearing….

    Note, this won’t work if a) you live on a filmset or b) hang out near a strip joint. Those looks are for the professionals only :)

  9. sophie doyle says:

    i crossdress to just fit in with my family as both my mums and my three sisters think i should have been a women and have always dressed me in girls clothes, and called me sophie.

  10. Vanessa Law says:

    Hey Sophie, thanks for stopping by – welcome. That’s an interesting way to start crossdressing, one I’ve rarely heard. Do you know why your mom and sisters thought you should’ve been a woman? Do you resent this, or has it been a blessing in your life so far?

  11. Jessy says:

    I started to crossdressing when i was 12 yrs. (now I’m 42) with my sister’s bra and panty. Now i buy my own woman’s clothing including Bra, panties, wig, cosmetics and shoes too. But im a secret CD never done in public. Every night I have been dressing in female clothes and sleep with it, for years and the feeling is fantastic. Now im very desire to going out but no company and shy. Im never been friends to other CD’s. I’m planning to A holiday to abroad, and going out to public as a woman, what sould i do. I need help.

  12. Justin says:

    Jerry I myself am like you I started when i was seven starting wearing my sisters clean bras and underwear they felt great and for a long time turned me on a great deal im 21 now and the urges to be a woman are even stronger ive always known i was meant to be a woman and have dreamed alot about it. I too am starting to look more into going out into public dressed as a female starting suttely by wearing womens clothes under my own or thick hoodies and pajama pants to cover my bra and longer tops as well as my yoga pants which i have quite a liking for. I neither have company to go out with nor really the support from any girls or guys in town and has become kind of lonely. In time though I can tell you we both will be able to go out happily dressed the way we want to feel and dress.
    Happy trails

  13. Ragina says:

    Hi Justin, I’m Ragina. Just a suggestion to you about going out dressed. Why not just go for it and go out all dressed up. I know that it can be a very scary thing to do at first, you need to build your confidence. Try to go out at night for a while when there are few people around and just walk around your neighborhood. If you have a dog that needs to walk, why not use that time to your advantage. Get dressed and go. then, after you get used to being out, move it up a bit. You’ll be surprised at what can happen. The biggest part of being out is to be confident in yourself. Stand strait, look like you belong there and don’t be afraid to meet people’s look and smile . You’ll feel better and more people will not bother you. And if someone does try to “out” you, be nice to them and not defensive. You never know, you may even make a new friend or two. Good luck. Stay safe, be pretty and be yourself. Let us know how it goes.

  14. Justin says:

    hey Ragina thanks for the advice and vote of confidence I just have a hard time building that confidence cause i know as soon as someone meets my eyes they will know im a man still and I cant do much about it until i get some facial features changed eyebrows waxed make up done right and so on and so fourth my shadow of my beard always shows and its just hard to really be a woman at this stage i need my ears pierced with some nice earings to go with. maybe some colored contacts or something idk im just worried about meeting peoples eyes i have gone out but not far just had enough courage to walk from my front door to the front of the house and into the garage but thats about it. I want to go out but i just know my facial loks right now arent to standard to even pass as a woman with a wig on and a full cute outfit its quite unnerving im working on telling my parents and seeing the doctors thursday about hormones to try and start growing breasts naturally and try to get some hips

  15. Ragina says:

    Hi again. I can relate about the confidence issue. The first time I went out dressed was several years ago. I worked in construction and the big boss would let me use his camper trailer at the yard when we were out of town as security. I’d be in bra and some makeup and would take my time checking the area. I loved it. Be patient dear and it will come to you soon enough.

  16. Steve says:

    I have been a secret crossdresser for 35 years – until I met my wife (8 years ago) – this had been between myself and my maker.
    To start with, my wife accepted my “hobby”, even buying me clothes – but soon after we were married – she threw everything out and left me bereft of any clothes – Recently, she has become more accepting and once more – I am “allowed” to wear female clothes as long as she doesn’t have to participate or even see me wearing them
    Any advice welcome

  17. redchaturtle says:

    Hi Steve. I'm currious why she would be OK with it and even buy you the clothes in the beginning then all of a sudden she didn't want anything to do with it. Did something happen? Was there more to your story than mentioned? I have a BF that was a secret CD for 34 years until he met me. I had bought him everything he needed to be a woman. From clothes and undergarments to makeup. Even down to scented lotions and womens deodorant. The only reason I would ever think his need for this was unaceptable is if he took it too far without my knowledge by going outside of our bedroom. Or by possibly competing with my femininity.

  18. why don t you meet other T girl s or cross dressers then you can go out with them ( see if you can get changed at there s)….have your night out then change back to male roll, that way your wife won t mind……..

  19. Naomi says:

    hi redchaturtle
    you dont say if your male or female and if your female then you really have no idea how your friend is feeling
    he should be able to compete with you as an equal and not to compete with you as a male dressed as a female against a female proper so to speak
    let him out of the bedroom it is his right to show as much of his femme side as he feels he needs to do otherwise he will you say he was a secret CD for 34 years he still is if you keep him trapped in his bedroom
    if you love someone let them fly if the love is true they will fly back to you
    teach him to dress and make up it will give him hope that you may repent and allow him to go out dressed
    try it with him one night and see how few people even give him a glance he will be a good age now so people tend to look less at older women that are dressed quite subtle
    be aware of his feelings and not just your own and dont be scared of him being more feminine than you are xx

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