Learn how to pass as a woman

Have you been out dressed in public before?

If you have you probably know the fear that comes with taking those first steps out into the world, and the constant anxiety of being read. Passing in public is the holy grail for crossdressers, but too many see it as an impossible challenge far out of reach. It doesn’t have to be.

On Crossdresser Heaven you’ll find many articles on how to crossdress – you’ll learn about the importance of smiling, how you carry yourself and the subtle cues that give your secret away. What you wear can be just as important as your mannerisms and voice. As you browse the site you’ll find advice on how to choose the appropriate clothes, as well as where to find larger size clothes and shoes that will fit you better.

If anything stands out about our community it is the sisterhood that we share. We learn and grow together – our mistakes and discoveries make it easier for those who follow to blossom. So instead of writing another article on how to crossdress, I want to hear from you:

What works for you? How do you ensure that you pass in public? How do you react if you’re read?

I encourage you to take a moment to share some of the wisdom you’ve acquired in your journey. It might just be the distinction that a new girl needs to get her started.

Advice for how to pass as a woman

From the Crossdresser Heaven community: – scroll down to the comments to see the advice and add your own!

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Latest posts by Vanessa Law (see all)

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46 Comments
  1. Author
    Vanessa Law 3 years ago

    I’ll start us off – smile! You’ll not only be more approachable, but have you ever noticed how men seem so serious, and woman smile more often?

    As a side benefit, you’ll feel better too 🙂

  2. Author
    Vanessa Law 3 years ago

    One from Emma on Twitter, “just wear old trainers, baggy jeans, plane top and zero to very little makeup. Like 99.9% of women do..”

  3. Bobbie 3 years ago

    I feel that when women do this they don’t appreciate the awesomeness of wearing some makeup to look beautiful and the pretty clothes / outfits they can wear.
    Bobbie Carr

  4. Jessica Anne 3 years ago

    I have dresses since 1957 I was cought be mother and taken to a shrink who had me dress all summer 100% of the time I enjoyed that time several girls visited me dayly did make up etc and I learned to service girls as a lesbeon The experiment did not work I wanted to dress all the time. I got the guts to go to Trenton and ask the owner of a bra & girdle shop to fit me in a girdle she first made me buy panties then she measured me and we talked of breast size she advised B I went with her advice got 2 allinonegirdles red & bkack stockings & red pumps 2 in heel as I stood in fitting room I was offered a deal ten hits on my girdled ass with a wide leather belt for everything above free. And I would leave the shop wareing 1 outfit under my street closes I did it and gave. The. Shop owner a big hug and thank you she told me I needed straping and she will do it for me in exchange for underware a super deal for me Bought shirtwaist pink dress across the street at Lane Bryant size 18T. With my long hair and make up I passed on the street. I married my life mate at 25 and was steralized with in a year as I did not want a child to be like me. The down side was watching wife screw to get with child yes I was secured in a mission style chair each time a stud was found. Raiser 2 girls both very smart they truly love me yet they were told early on of there father they have been a great help with my feminazation and stand close to this date(2015) I never wanted to sex change I did hormone and got natural tits not quite a B 40. It was fun as things happoned the 3hr with breast pump for 4 years
    Today I live 7/24 as fe male and pass wife is considered a sister where we live and we have no regreats as to the last 55 years at home I am always in a allinone stockings and 3in pumps ware plain shirtwaist dresses to go out life has been a ride but I would do it all over. Jessica anne

  5. Author
    Vanessa Law 3 years ago

    From Google+, Harley says, “Living ” full time” I personally “pass” at a glance. even for a few minutes. Genetics played a bit of a trick on this preop transwoman. Even after 5 years hrt I am still not exactly the built femininely 5’11” makes for a good sized girl even at 165lbs. No matter though, whatever others think is for me irrelevant, though I understand the concern many have. These are the same feelings that I experienced early into my transition. What I would like to highlight hear is a simple thing I have learned. With very few exceptions what Churchill said long ago. “We’ve nothing to fear but fear itself”. If you are comfortable with how you present yourselves. Few will do more than look right through you. Most will respond no differently than they do to any friendly outgoing person they meet.”

  6. geni47 3 years ago

    When you go out en femme “act” like you are supposed to be there! That will help you to blend in.

  7. Elle 3 years ago

    When going out, like shopping, or lunch, walk in the place with a smile and head up. Walk in like you own the place. Look at a sales clerks or waitress name tag, call them by name. Make eye contact. And most important dress to blend in.

    • Joseph Galvan 2 years ago

      I agree I dress conservative

    • Author
      Vanessa Law 3 years ago

      Elle those are great tips! Smile, be confident! Others can sense your confident energy, and will react to it as well!

  8. JinianVictoria Herdina 3 years ago

    Quickest answer is simply I don’t care if I am read or not. If anyone has a problem with it its exactly that their problem not mine Simply be yourself..be the woman you think and know you are. Would she slouch? Would she not look at people or smile? CERTAINLY NOT! Dress your age, dress to blend in to the surroundings. I have been stopped a few times by police but was always treated professionally and with courtesy. The same goes for going into stores or wherever else. Remember most people don’t notice what is right in front of them unless you appearance is jarring for some reason chances are you wont be remembered after a few seconds.. If its your first time out dressed go with a friend…….

  9. Marsha Savemore 3 years ago

    I agree with the other ladies… My first time in Public was nerve “racking” to say the least… I should have gone with someone with me… but I ventured alone… Drove to the local Taco Bell down the street fully dressed in a rental car and “tested the waters”… so to speak…

    I went thru the Drive-thru and ordered in my best enFemme (falsetto) voice and then went to the pick-up window… the girl and boy at the window collected my payment and handed me my purchase… with a smile I said “thank you” and they replied “Have a good evening Ma’am”…I was thrilled!… I smiled and drive back to my Motel room ( I was out of town on a jobsite)… it was most thrilling… I was so nervous… even the front desk clerk (a girl) was very receptive to my attire… she smiled as I walked past to go to my room… I expected stares and snickers… Just was acting like I was tired and hungry but a Lady regardless… and they seemed to believe it… I hope everyone has such a wonderful experience… but be careful it has been a few years since I did that… and people are acting pretty ignorant in some areas.

    With Friendship and Love for my Sisters… Marsha

    • Author
      Vanessa Law 3 years ago

      Wonderful Marsha! What an empowering first experience! Thank you for sharing love!

  10. Amy 3 years ago

    What works for me is just be “yourself” i dont want to do a “put on” to seem female….Im just me and just be yourself i feel

  11. Jodi 3 years ago

    Hi, I used a theme party to go out in femme for the first time. It was a great way to test the waters, it also gave me confidence. The funny thing is I thought I looked terrible, but the comments I got was anything but, some people couldn’t even tell. In hindsight I believe we are our worse critics…as the night went by I became more confident and relaxed, in the end it appeared that no one really cared.

    • Author
      Vanessa Law 3 years ago

      An astute observation Jodi!
      It reminds me of public speaking, no matter how nervous you may feel, very very rarely can anyone even tell.

  12. Krissy 3 years ago

    The first few times out were the hardest 4 me, but regardless of how you look, you’ve got to f’ing OWN IT! The way I see it, when I’m out in public as (Slutty) Krissy, it becomes MY world. From the moment I step out of the safety of my car, in this episode of life, I’m gonna B the central character! That’s right, they’re in MY world, and I’m the STAR!! And I JUST GLOW because I am so F’ing UNIQUE!!!! I’m no drone, or Lemming..I am Krissy and one of a very SPECIAL group of people who are brave enough to EMBRACE their innermost desires. And that carries over, and people pick up on your happiness, and Life just turned GOOD for the rest of your outing. U R in da ZONE, baby!!! PASS!

    Wishing YOU the very best in life,

    Krissy

    • Author
      Vanessa Law 3 years ago

      Way to own it Krissy!! Your confidence is magic

  13. Krissy 3 years ago

    I like your style..cut right to the bone!

  14. rodney 3 years ago

    I’m a first time crossdresser I’m 52 years old I’ve only been doing it now for maybe 4 months can anyone give me pointers for going out PLEASE !!!

  15. Sarah 3 years ago

    Research is the key. Once you’ve decided where and when you’ve going to venture out “en femme”, go there at the same time and observe who’s there, how they dress what they are carrying what they are doing etc. Then when you go dress and act in a similar manner and you’ll blend in. For example a smart skirt suit and heels works well in the City of London during the day, but would stand out in a less affluent area doing the grocery shopping.

  16. Charlie 3 years ago

    I know it was very scary for me to go out for the first time in public. I started out with baby steps first and gradually increased it each time. The thing to remember is that most people out there are not really paying attension to there surroundings to notice you. It is a confidence builder every time you go out

  17. Author
    Vanessa Law 3 years ago

    Rudy from Google+ says, “Being cool under pressure and dressing to be invisible has sustained me quite well while being out an about.”

  18. Janie Debruyere 2 years ago

    When I go out I dress my age and appropriately for the venue . Most people don’t pay close enough attention to even notice minor imperfections. My first time out I was half scared to death . It took half an hour to convince myself to get out of the car and walk into the goodwill . When I did the sales ladies were wonderful. I even had a nice conversation with one of the sales girls about her recent vacation while she helped me find d a blouse to go with the skirt I had picked out. If she noticed I was not a gg she never acted that way. I believe I was lucky that my first time turned out to be so much fun. If that experience had been bad I may not have tried again for a long time, if ever.

    • Author
      Vanessa Law 2 years ago

      Wonderful Janie! You’re so right that most people won’t notice minor imperfections, in fact, most woman have imperfections of their own – it’s part of being human 🙂

  19. Bobbie 2 years ago

    I am still in the closet with dressing. I do hope that I will look good enough to go to a club and pass as a woman. I see many suggestions how to dress just to go to a store and feel confident enough to enjoy myself. Thank you for all of the suggestions.

  20. Robin Michaels 2 years ago

    Wow it was such a wonderful thing when I first went out, and I loved it. For me when I bought my first wig and makeup did I start thinking of going out in public, then I got the nerve and shaved my legs, chest, and arms. Now I was full of confidence and my desire was just incredibly strong. I ended up going to a mall in a different city and enjoyed ever moment, and the more I was Robin the more by confidence grew. I always try to dress as a 60 year woman would, except I always go in my Sunday best, want to look my best.

  21. sammy magdaleno 2 years ago

    When i crossdress i go to the cemetery or to a public park & i usually wear a short sexy flary floral skirt with a pair of satin panties underneath my skirt & a long sexy auburn red wig. I always pass for a sexy woman bcuz i aways get stares & whistles especially from the mexican workers at the cemetery so i usually bend over a little to get a closer look at a plot & the workers always get behind me & all of sudden start digging for weeds as they’re looking up my skirt trying to see my panties. That’s when i bend over even more so they can really get a good view of my sexy satin red panties under my skirt. One time i was so bent over that the wind lifted up my skirt above my waist & my underwear was fully exposed & i even heard the worker say whoa! really loud to himself. That’s when i stood up & pulled my skirt back down & smoothed my skirt. I looked at him & he had a big smile on his face. I got the hell out of there & as i was walking away i heard him say out loud “nice panties!” I guess i showed a little too much but as nervous as i was, i really got turned on & i enjoyed the whole experience.

    • Ariana Merona 11 months ago

      OMG that sounds so hot!

    • Joann1947 2 years ago

      I like to go out in my car and flash truck drivers they like it and it really turns me on next time I am going to try to get one to stop and I will see what happens

  22. lisa 2 years ago

    i like to drive around at night in a tight sweater, i use water balloons for boobs cause i like the way they jiggle, full make-up and a wig and of course my high heels. Sometimes i’ll stop and walk around not far from my car just so i can hear my heels on the pavement. I like how you always have to adjust your bra straps and pantyhose. It’s funny how as soon as i step into my panties my penis knows to turn into a clitty, and it won’t turn back till i get home and pull my panties down.

    • Gabby 1 year ago

      I too luv to drive around dressed up, showing cleavage , I tried to pull up next to bus drivers or truckers showing my cleavage and Sexy legs, makes me feel naughty and really sexy

  23. Sharelee 2 years ago

    I have been out several times in Newcastle city centre by day and the metrocentre ( once). Apart from a few rude and ignorant ‘amazon’ women, most people are ok when they realise I am not a real woman. I still have to be aware of groups of young lads, but most times I can see them coming and avoid. I have found that dressing down in flat shoes, but still with a short skirt and thick tights with a little more subtle make up, helps me to blend in and not get embarrassingly noticed. I have a big nose and an ugly face, so I do get ‘read’, but I need to be a woman so much, I have to go out. It’s not just a sexual kick, but a deep need to let that woman inside me out! I still dream of being a real girl, even though I am 57 and a father of two teenage girls. My wife does not allow me to tell them or anyone of my habit and says she couldn’t cope if I ‘came out’. I can’t risk my marriage or my children’s contempt, but my feelings get harder to cope with as I get older. I feel unfulfilled and unhappy, as my menopausal wife has not wanted sex since 2008 (nothing to do with my dressing either). I have not cheated on her, by the way. Anyone any advice?
    Sharelee x

  24. Gazzmen 2 years ago

    Gone out fully dressed twice both on halloween one to the store got ,lots of smiles not passable once to a gay friendly neighborhood very exciting

  25. Janine 2 years ago

    I have been going out dressed for a couple of years.
    The more that I do it the easier it is.
    The hardest thing for me was getting makeup to look right.
    Finally I decided to go out dressed and go to a mall and find a store that offers to do makeup.
    I was extremely nervous about doing it but once I got to the mall and went into the JC Penny’s I found what I was looking for.
    There were three girls who worked there who did makeup and only one of them was busy.
    Taking a deep breath I chose a girl who was about nineteen or twenty and walked up to her and in my softest voice I smiled at her and told her that I wanted her to show me how to put on makeup on.
    She realized that I was a man dressed as a woman but didn’t seem to mind.
    I got seated in the chair and she went to work on my face.
    She removed the makeup that I was wearing and started with a beard concealer .
    I watched her as she was doing my eyes and lips until she had transformed me into a fairly good looking girl.
    While she was working on me she was explaining what she was doing and what she was using on me.
    After about a half hour I couldn’t believe how good that she had made me look.
    I bought a hundred dollars with of the makeup she was using and as I got up to leave I thanked her and tipped her Generously as I walked away with a new sense of confidence.
    That one time taught me a lot of things so that I could do my makeup a whole lot easier and quicker
    If you can get past the embarrassment of asking for help you will never regret it.
    I know that I didn’t.

    • Karri Roses 6 months ago

      Great story, Janie!! I commend you for having the courage to ask for help in putting on makeup. I think if I did what you did, I would do it on the other side of the city where I live so no one I know would recognize me.

    • Erica 2 years ago

      Next Wednesday I am planning for a morning and afternoon and getting out! I made an appointment to go to a Spa and have them do it! I can then change there an be on my merry way. The price is $35 and I think that’s reasonable. How much to tip?

  26. John 2 years ago

    I love to walk around the house in my sundresses when no one is home or go outside on the back deck. I’ve never tried just driving around at night or anything else

  27. Amanda 2 years ago

    I usually only go out dressed at Halloween, Mardi Gras, or to a fetish ball. So about three times a year. I spend months anticipating. I went out with a lesbian friend once to a club. That was fun, but I didn’t pass. I don’t think I could ever “pass”.
    I ,do, wear womens shoes most of the time, and I shave my legs. The shoes are mostly unisex type such as penny loafers or knee boots that I wear under my jeans.

    Smiles
    Amanda

  28. Toni Ginamaria 2 years ago

    My first outings back in 1990 were to gay bars hair dressers and shops out of town. I would go out Dressed As a Boy DRAB first and later in the day in DRAG. My spidey sense was off the charts, but as nothing bad happen and what did I could handle, I became more relaxed. I got drinks bought for me doors opened and cigarettes lit propositioned by some, other times I would attract admirers that would hang around and look down at their feet and talk awkwardly till I would take the lead and flirt and reassure them. I would smile look them in their eyes play with my hair and brush against their arm or touch them on the thigh. Eventually I would go shopping ask for advice and try on in the dressing room before purchasing. I wore 4″ heels around the house and packed flat slippers in my purse. I practiced my make-up skills, went for applications at the hair stylist and department stores. The advice I got was to prep my skin shave clean tone moisturize. As for make-up less is more. My girlfriend would tell me that department stores work on commission drug stores are more affordable and you can return anything that doesn’t work. Note I have never before returned anything, ever. Go easy on the eye make-up, less slutty/ clownish rather more natural, better appearance to blend in with natural women. Watch how other women dress in the places you are going. No leather outfits short skirts and high heels at the grocery store. Try to copy to blend in and not to stand out. Sweater if you don’t yet shave your cheat & arms tank top cardigan or blazer if you do, jeans and mid-heel boots or flat unisex shoe. My mom advice: go easy on the perfume to always stand up straight look people in the eye, ask for things in the form of a question smile often and say thank you. And finally don’t worry about what other people think unless they pay your bills. Get dressed put on your make-up and a touch of perfume grab your purse and go out stay safe and have fun.

  29. Sallysim 2 years ago

    My first outing was with my girlfriend just a few weeks ago. We went to the local 24 hour supermarket after we finished work at midnight. I was a bit apprehensive at first but then began to feel so at ease as we shopped for clothes etc. Nobody there including staff gave me a second glance, if they did I didn’t notice. Except one of our customers in the pub saw us and called me by my drab name but even he didn’t make a big issue of it. We’ve been out a few times since and I’ve been out on my own en femme with her encouragement. But we still plan to go out for the day or to a restaurant for a meal as soon as time will allow. I’m desperate to go out more I feel so free and confident. I’ve not had a bad experience yet but I’m sure I will have someday. But look forward to bringing Sally to the fore this new year. Ok I get some stick from my customers ( we run a pub) so it makes things a bit more difficult as you don’t get much privacy. But I use our weekly auiz night as a release as Sally hosts the quiz. At first there was a bit of ridicule but I’ve had lots of support and good comments from both staff and customers alike. Some say I look better as a woman than a drab man and others say do what you feel good with which is encouraging
    I think 2016 is going to be Sally’s year
    Take care everyone out there love to you all.
    Sally S xxx

  30. Debbie 2 years ago

    Hi everyone! Just thought you might be interested in knowing I have been dressing secretly for years (I’m 68) now on hormones. I have started going out dressed ln Newcastle upon Tyne for the last few weeks at night to bars in the gay area. I do not pass yet but it is getting better each time I go out. I love it it feels so right.I am married and my wife knows and shops with me.However my grownup children do not.

  31. Debbie 2 years ago

    Debbie here again, thought you might be interested, I was out again last night (the weather was terrible ) however the bar staff and the few customers who were in secrets bar on Scotswood Rd, we’re really friendly. I will be going there again.It felt so right I only wish that I could go anywhere and be myself.give it time and who knows.

  32. Rebecca Williams 2 years ago

    I have been going to a group I Phoenix called Arizona Tgirls. This gives me a chance to go out without people giving me a hard time. It also gives me more confidence to go out. I suggest that if you have a group like this in your area that you join them.

  33. Gracie Garcia 7 months ago

    I was apprehensive the first few time I stepped out dressed. The first time trying something new is like that. Overall I had no problems and people made no comments or pointed fingers. Actually no one paid attention or noticed for the most part. Those that did glanced or smiled approvingly which gave me confidence. Houston and here in San Antonio are very gay friendly but attitudes in Texas are changing and some of my old fears are coming back.

  34. Sarah 3 months ago

    Every time I use the bathroom, my panties get wet when I pull them back up. Any suggestions on how to prevent that?

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