19 Steps To Crossdress and Pass

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.

38 comments

  1. Jane 27 July, 2015 at 00:01 Reply

    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.

    • Vanessa L 28 July, 2015 at 21:51 Reply

      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.

  2. Heather 13 July, 2015 at 10:58 Reply

    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!

  3. Karla 13 July, 2015 at 10:18 Reply

    There´s one very important thing that really helps in crosdressin succesfully, it is: SMILE
    there´s nothing more charming than a femenine smile and sometimes we are too worried about our outing and we forget to smile, smile as you go out, smile if meeting someone at the door, smile at people you meet walking along the sidewalk, smile as you walk or wait or whatever, SMILE!!!
    it never fails

  4. Wendy 7 July, 2015 at 06:59 Reply

    Such good points. From my own experience of going out for the first time at the age of 62 I was so worried of being found out, but your point 3 is absolutely spot on. It is all an illusion. In generally we all see what we are expecting to see and the important thing is not to stand out or do something that provokes the illusion to be questioned. Good shoes and accessories are essential to finish off our look and perhaps complete the colour co-ordination.
    Thanks for looking after us girls so well.
    Love Wendy

    • Wendy 7 July, 2015 at 16:41 Reply

      Hi Girls,
      I forgot to add one more point from my experience. Always give a smile, especially when looking at another women, it’s expected and a nice part of the illusion. It’s an important woman thing as men just don’t do it.
      Love Wendy

  5. Loni Kay 6 July, 2015 at 03:54 Reply

    After the shaving,and putting on your makeup,and most of all those gorgeous heels are on,everything is on.I know that I’ll be safe and the nervousness fades after the first look you get from that hot guy that tells his friend he wants you.There is nothing more exhilarating in a gurls life than to feel like a sexy woman…Loni

  6. Candy 5 July, 2015 at 08:49 Reply

    I live by this advice, Always go out efem never have a problem. I go every wear dressed up. Every crossdresser should follow these tips.

  7. How to be a feminine guy? - Empty Closets - A safe online community for gay, lesbian, bisexual, transgender people coming out 5 September, 2013 at 17:45 Reply

    […] Actually, a lot of gay guys really like the androgynous look. As long as you're still packing a penis down there, you could otherwise look as feminine as you want and gay guys will be willing to date you. Straight women might be more difficult to appeal to, since most straight women want a "man" and even the most progressive-minded of women can have problems with a boyfriend who they perceive as more feminine than they are. But be who you are, don't change yourself to try to appeal to anyone else. You will find someone who will love you for who you are. ———- Post added 5th Sep 2013 at 05:22 PM ———- Well, the cool thing about expressing femininity is that there are MANY ways to. I'll tell you what I did, though, in an effort to while in high school: since I was an angry, depressed kid into the metal scene, I did grow my hair out, and made sure it was as straight and long as possible. Hardly anyone grew theirs out, but after that, I noticed it started catching on (coincidence?) with others. It was also popular for guys to paint their fingernails, at least black, and to experiment with eyeliner, so I did that from time-to-time, too. Didn't really have enough self-awareness and courage back then to wear female clothing in public; it was thought of as some shameful fetish back then, but on occasion would wear panties underneath. With my small frame, gentle mannerisms, and soft features, I think I could at least throw some people off today. I'm more comfortable going out as myself, androgynous, while pulling off "lady mode" at home, since I'm still not comfortable being seen, yet. Start small, and work your way up from there. Unfortunately, yes, the whole "middle ground" while transitioning, even if simply a change in attire, is one of the most challenging. Passing is a constant concern, but you can't ever be sure, so you do your best and go out with confidence. Act like a woman and think like a woman, but don't force it: be yourself, you're still an individual. Also, I wouldn't worry too much when it comes to dating right now, but I'd say give the TG community a shot, where there will be much more understanding and support. Me, I'd present as a male in public for now, at least until you're more confident and prepared that you can pass, which doesn't happen overnight. This page might prove helpful: Some Tips for Passing as a Woman | Crossdresser Heaven […]

  8. Samantha 17 June, 2012 at 14:46 Reply

    I agree with the advice.Dont dress to attract attention or you will probably do so for the wrong reason.Wear the best most lady like clothes make up shoes and accessories you can afford. Make sure things are coordinated. Practice going out in quiet places to begin with. Maybe go for a drive making sure you have full control of the car in your girlie shoes or boots!

  9. Tammy 23 March, 2012 at 10:37 Reply

    I dress for relaxation I don’t try to compete with wemon and there dressing . I just like the way the clothes feel on me. I just do it in priviate so i don’t try to with anyone .

  10. Casas rurales en Salamanca 27 November, 2011 at 16:56 Reply

    Thank you, I’ve recently been looking for info approximately this subject for a long time and yours is the greatest I’ve discovered so far. However, what in regards to the bottom line? Are you sure in regards to the supply?|What i do not understood is if truth be told how you are not actually much more well-liked than you might be right now. You are very intelligent.

  11. Lizzie 14 September, 2011 at 19:36 Reply

    INcidentally, aboiut watches: (I just re-read my post from a year or so ago). You can find really good smaller watches in antique malls. Elgin’s first waterproof came out in about 1920, and measures about 1″ in diameter. It was marketed as a men’s watch, but in this era will pass nicely as a ladies. The same thing goes for 1920-1930 Bulova tank shapes. They are smaller than the modern ones, and will pass nicely as either a men’s or a ladies watch. Either of those are available on ebay and in antique malls for about $100.00, in gold-filled or sterling cases.

  12. Elizabeth 14 September, 2011 at 19:27 Reply

    WHenever I am considering going out, be it to the local convenience store for gas and coffee, or to dinner and a show, I think about what my (now ex) wives would have worn. For casual day wear, I dress as my wives used to when they went to work. For evening wear, unless I am going to a really dressy function (think one where if you went as a man, you’d feel comfortable in a tuxedo) then I forego the little black dress, and CFM heels. If I am not wearing the little black dress, I use eye shadow that is lighter, and more nearly approximating my skin tone. I never wear false nails or eyelashes; they are just a little too “over the top” and will get me busted every time. 

  13. Staci 26 June, 2011 at 22:19 Reply

    Thongs/G-strings, lingerie, skirts, perfect fitting dresses, make up and so much more – the right heels is by far the sexiest and most femanine thing you can do.
    I agree about the stripper heels – DO NOT go out on the town in those unless it’s October 31. Not being bossy, just a suggestion. I have some 6″ stripper heels – the clear slutty kind. They are all kinds of fun, but bring me to a total height of 6’7″.
    3″ – 4″ heels seem to work best for me. Makes my feet look perfect. Now if there was something I could do about my hidious mug and my Sasquatch body hair, I could go somewhere.

  14. Callista 26 June, 2011 at 15:02 Reply

    Wear Tall, tall, tall heels! (But not hooker heels) trust me, this helps! (and learn to walk in them, too). It will make your feet look smaller.

    Tone it down with the clothes! I know, I know we can’t help being dressed better than the GGs ;), but if you wear something that’s a bit more in style rather than the most frilliest, daintiest, bedazzling thing you can find, you won’t get as many strange looks.

    If you are muscley/stocky, work with what you have! Pecs can be turned into sexy cleavage with the help of tape, and man boobs can be turned into luscious melons with a nice push-up bra. If you happen to be ‘top heavy’ (like a gorilla 😉 ) try waist cinchers, girdles, and hip padding. Trust me, if you got enough booty, no one will be the wiser. And wear puffy sleeves for big arms, rounded necklines for broad shoulders, and knee-length dresses (or longer) for big, muscly thighs. For hands, make sure to have long finger nails and lots of big, gaudy rings to take attention off your big hands. :)

    And girls… Learn to do your makeup! I can’t count the number of times I’ve seen girls with cake-faces that look like surprised porcelain dolls. There are lots of tutorials on youtube. Unless you’ve been blessed with a feminine face, you gotta work a little to make your face look feminine. There are many tricks like softening the jawline with bronzer, concealing eyebrows, etc. One thing that I usually notice is a dead giveaway is the jawline and the mouth, or the bottom of the face. Try to make your lips look pouty as opposed to large, and that will make the bottom of your face appear smaller. Play around! Look at pictures of more “masculine” Women, such as Heidi Klum or Brooke Shields, and pay attention to what they do.

    And don’t overdo it with the mannerisms! Maybe there are few ladies left nowadays, but it doesn’t mean that you should start making plans to invite the Queen for tea. :) You got to build it up, get used to it, make it subtle… If you exaggerate it, you will look like a caricature of a woman and people will notice you.

    That’s all I have to say for now girls… Now go have fun! :)

    -Callista

    • Vanessa L 1 November, 2009 at 12:36 Reply

      DG, it’s a good resource of crossdressing advice. It doesn’t substitute for practice or personal femininity training. If you’d like to be more feminine it’s a good place to start.

      • Ragina 7 January, 2010 at 15:50 Reply

        Hello all,
        I, for one am not overly concerned about ” passing ” per se, I really just want to be able to go out somewhere and not be stared at or spoken about behind my back or even snickered at as I pass by a group of people. Not that I try to be read, I just want to be myself. Of course, there will always be the one person in a crowd to make a big stink about a crossdresser in a crowd. I’ve seen it happen more than once and I cringed for the person being the brunt of those comments. I only hope that some day that we will be accepted as a normal part of society. In the meanwhile, I’ll still continue to be myself, like me or not.
        Love to all, Ragina

  15. Lizzie 13 February, 2009 at 23:47 Reply

    A little tiny wrist watch will make your wrist look even bigger. Pick either a very small unisex watch, or a lergish ladie’s watch. I know one TG woman who insists on weaaring a little tiny (0/0) ladie’s Bulova that is a very good watch, but it looks lost on her large wrist bones. I am a clock and watch repairman, so I notice these things, but you would be surprised how many watch collectors there are out there, both male and female, and believe me, all collectors notice everyone’s watch.

    • Vanessa L 15 February, 2009 at 12:18 Reply

      Lizzie that’s a great point. It’s about proportions, anything that looks “too small” will accentuate how large you are. Whether it’s jewelry, a watch or that too short skirt.

  16. Fitting In « The life of a Two-Spirit 5 February, 2009 at 20:05 Reply

    […] Some Tips for Passing 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. […]

    • Sally 15 May, 2010 at 05:51 Reply

      Nice web site. One tip related to being calm, is not to look at everyone for a reaction…(to see if they read you or not). The thing is, we can't read minds, so even if we get an odd reaction, it might not be what we think. It can destroy your confidence. It is best to carry on like you belong, like you have done it a million times before. And one really important tip is to always hold a smile on your face and smile to everyone who makes eye contact.

  17. Lynn Jones 23 January, 2009 at 14:51 Reply

    Some interesting advice. thanks for sharing. I think passing’s nice if you can get it, but I think we can get hung up on it. If you’ve got a very male body – big shoulders, strong jaw, etc – its unlikely you’ll pass close up (I know I never would), so why sweat it? Just go and enjoy your day. :)

    The ‘fear’ one is particularly true – regardless of how you’re dressed. What about:

    Smile more… just, maybe not as much as The Joker would. :)

    Oh, and practice walking in your footwear before you leave. If the shoes aren’t right, they’ll cripple you by the end of the day.

  18. Molly 23 January, 2009 at 08:17 Reply

    You left out one,
    Never go shopping or in public places with other xdressers if you don’t want to be “read”

    loved you article

    Molly

    • Vanessa L 23 January, 2009 at 09:13 Reply

      Molly, too true :)
      Allyson, I can see how we sometimes go a bit overboard with the accessories. For myself I probably go out too light on accesories – I’m not sure where I missed the desire to over accessorize :)

  19. Allyson 22 January, 2009 at 14:09 Reply

    Can I add one?

    Coco Chanel had a rule about accessories: on your way out the door, take one off. Accessorizing is much more art than science, and less is almost always more.

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