19 Steps To Crossdress and Pass

Do you pass as a woman?

Passing… it seems like the holy grail for crossdressers. If we could work hard enough, lose that extra pound and practice voice lessons for another hour – maybe, just maybe we could pass as a woman. In our minds we’ve build up passing as something elusive that is to be dreamed about and never achieved.

Yet passing is closer, and easier than you’d think if you let go of the notion that everyone, all the time must only every perceive you as the woman you’re trying to impersonate.

Here are nineteen practical tips from Kelly Stevens for how to pass as a woman. If you’re serious about passing you’ll find more high quality advice in the world’s best crossdressing guide.

How to Crossdress and Pass 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.

And there you have it – nineteen practical tips for crossdressing that don’t require night classes or intentisive training. Don’t stop now, there is so much more to learn about crossdressing – learn how to pass as a woman.

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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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Latest posts by Vanessa Law (see all)

  1. Profile photo of Danielle(Dani)
    Danielle(Dani) 1 week ago

    I can say this. I have been blessed with lashes. All the men in my family have them and none of the genetic women do, go figure. My grandfather had to cut his to keep them from rubbing his glasses. My brothers and I have always received comments from women we meet about how jealous they are about our eyelashes.

  2. Profile photo of Linda Roach
    Linda Roach 2 weeks ago

    I’m sixty eight, but want to dress like a twenties something chick. I also don’t care to wear regular clothes and sensible shoes, I want to dress like a female lounge lizard. I care more about my lingerie than my outer clothing. I guess I’ll have to stay semi secluded and out of malls. I have under dressed all of my life and I think I’m too old to learn or care about passing. Good article though, good tips. Thanks for the info, even if I can’t quite swing it.

  3. evette 3 months ago

    i have been dressing for some time, im a older man 5ft.10in. i always wear my skirts short because that is the way i like them, i wear a 38b cup bra so not to be to big, inthis day and time not to many people say anything mosat just dont care what i have on, so dont be afraid just go for it love you all

  4. suesy 3 months ago

    i have a freind that is willing to take me to a gay bar dressed as a female should i go as a female help

  5. Profile photo of Karyn Lobelia
    Karyn Lobelia 3 months ago

    Love and kisses , this article is fantastic , but I have two comments . First learn how to,walk like a woman , and how to apply makeup and dress . For God Sakes go to gay bars or whatever BUT PLEASE DO NOT GO OUT TO A MALL OR IN PUBLIC IN YOU ARE UNCOMFORTABLE OR WORRIED BECAUSE IT WILL SHOW . The Law Of Attraction says YOU WILL GET WHAT YOU ATE THINKING ABOUT , If you expect or worried about something happening , It Will ! Gay bars or transgender friendly places are for you if you lack confidence ! Please do do expect ALL people to be kind , polite , and respectful no matter what you do ! Just try to find friends locally you can share time with and never be unkind .

  6. Jaye Dee 3 months ago

    That was a great article not only about “passing” but a confidence builder as well. I have been dressing as a woman all my life (50 plus years) and have adapted to almost all of your suggested tips. The only thing that I regret is not having the confidence earlier in my life to be who I really am, I AM A WOMAN!!!!!

  7. suesy 3 months ago

    im still scared to go out dress like a girl in public the complex i live in is a 6 unit complex and my grilfreind wont let me step outside in daylight dress as a female or at night when its dark out at night my family dont know im dressing as a female how do you tell them

  8. vikki 3 months ago

    I realize that everyone is different, and some have a harder time than others, but, I say your main accessory is confidence. If your going out—-don’t hide, and be proud of who you are. You will be surprised that your ease will make others at ease also!

  9. Katie 4 months ago

    Definitely smile …. and present yourself with confidence. But unless you have one of those fog horn male voices don’t be afraid to interact with people. Half the fun of going out for me is not being alone. Store clerks, restaurant staff … even casual conversation with a stranger can really make you feel good as a woman. Work on a feminine voice. (I practice on may daily commute).

  10. Stacy 4 months ago

    Vanessa, thank you so much for all your wonderful advice on this site. You are so inspiring. I hope that very soon I will have the self esteem and confidence to go out dressed. And with all your great advice, I’m sure I’ll be able to pass.

  11. Profile photo of dani
    dani 5 months ago

    I have been going out for some odd 40 plus years and have only been read twice that I know off. Once by teenagers at a mall entrance and once in walmart while wearing a coat not suited to my skin tone.
    I always dress age appropriate less about 10 years. Since my height is 5-10 I don’t push the heel height over 3 inches. For skirts don’t go higher than knee less about 2 inches. The skirt length should be at your fingertips. I don’t use false nails, they are too difficult to handle.My watch is a jewelled large ladies which takes away from the large wrist. Breast forms are a “C” cup. I use a waist cincher along with padded panty. Look at what women are wearing for the time of day you want to go out in. I use women’s washrooms, change rooms, eat in restraunts. I have had my colors done so I know what colours suit me. I know my sizes and carry a tape measure to check leg lengths/ blouse lengths etc. so I know what fits and looks good before I consider trying it on. My ears are pierced and I wear dangly earrings. Avoid to many rings on the fingers, it looks slutty and draws attention to hands. Do wear bracelets. With bare legs and skirt I always wear ankle bracelet, it takes away from my height.

    • Profile photo of Leonara
      Leonara 4 months ago

      Catching up on the forum. What a wonderful article. Thanks for sharing

  12. Stella 7 months ago

    You mentioned 52DD tits. I have a large frame and a 46″ chest and currently wearing a 46D bra. It sometimes feels too big. Should I go smaller? I’m still housebound, too afraid to venture out, despite the advice above.I probably think I’m not convincing 🙁

    • Profile photo of Danielle(Dani)
      Danielle(Dani) 1 week ago

      I’m in the same boat. I’m in a 48D now. I was bigger. I let myself get really fat unfortunately so I actually did sport DD’s for a while and just recently went back to my D’s and bought some new bras because I’ve lost weight. I found taking full length pictures of myself and turning a little to the side helped me see what was a little more appropriate for my size and shape. I’m continuing to lose weight so I figure I’ll wait and see somewhere in the not to distant future again what seems more appropriate and probably go down again.

  13. brenda 7 months ago

    I really want to dress up but im to afraid to go anywhere to buy clothes in case i get found out today i found a pair of thights in the street took them and wash them and wearing them can anyone help

    • Julie 7 months ago

      I buy a lot of my stuff online.

    • Stella 7 months ago

      I buy on ebay and collect at Argos.

    • Michele Luke 6 months ago

      I get most of my stuff at Goodwill. Not underwear, but dresses, shoes, etc.

    • Tammy 5 months ago

      Buy clothing at christmas

  14. Profile photo of Khloe West
    Khloe West 7 months ago

    Great read and much more to share when actually awake,. bit my “Schooling” advised a 38D….


  15. Janine 8 months ago

    I’ve been out many times and I guess that I must look passable .while walking out of a mall once I met a real female who told me that she just loved my skirt
    I smiled at her and thanked her as I was walking away
    Her compliment about my skirt made me feel really feminine and I had a little bounce in my step as I was walking to my car.

  16. Kayla Kross 9 months ago

    Great write-up! Thank you Vanessa, all these tips are very useful & workable. Confidence is the biggest key factor in my eyes when it comes to passing in public. One can achieve all the above mentioned tips but if one has low or limited confidence it just bleeds right through everything else. Stay positive & stay strong, true to your conviction & who you are. I love going out in public fully dressed to the 9’s, smile and walk proud. When I’m out in public it is the most empowering feeling I’ve ever had. Another key feminine characteristic is correct “posture”. As a man we automatically slouch our shoulders & slump over while day sitting at the dinner table. Posture is a key element in the female persona in my opinion. My tips…arch the lower back (stick that ass up in the air) tits up & shoulders back and relaxed. And confidence in every aspect you/I do daily.

    xXxX Kayla

  17. Vanna 10 months ago

    I am SOOOO glad I found you Vanessa! Empowered thanks to you and all the girls!

    • Vanessa Law 10 months ago

      A pleasure hon – welcome to Crossdresser Heaven!

  18. evon mc kay 10 months ago

    reneereyes.com has exercises for thinning your arms evon

  19. Jane 10 months ago

    Even when I follow many of the suggestions in this article in the end there is no hiding the fact that I am male-bodied. Thus I don’t try to disguise or deny the fact so when it comes to speaking I do try to speak in a softer manner but I do not avoid talking by pointing or other sign language.

    Usually I am accepted as what I am, a male-bodied person who, for the time being, wishes to be considered female. I’ve not yet had a problem and most staff have been polite and accepting. The worst I have ever experienced was some confusion and I alleviated that with a pleasant smile and a display of common manners.

    Overall I think people appreciate honesty from those of us who do not look like a svelte, young runway model. Your own confidence goes a long way.

    • Profile photo of Vanessa Law Author
      Vanessa Law 10 months ago

      Well said Jane,
      If you’re approached, or asked, honesty is the best policy – and being friendly and not getting defensive puts you in a much better position.

  20. Heather 11 months ago

    I think being confident is the key and just accept that some may clock you. Once you relax and realize I’m a guy in a dress so what? Do that and smile and you’ll be fine.of course all the other tips are great as well. I go out all the time and 90% of the time I blend and I even dress younger than my age, I can’t help it!

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