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How to Pass As A Woman – Don't Make These Deadly Cross Dressing Mistakes

Updated on July 12, 2009

Cross Dressing Tips For the Well Dressed Woman

So you want to learn how to pass as a woman? For most people, cross dressing is about expressing their inner self, exuding glamor, style, and class. It is NOT about slapping on some costume makeup and a skimpy dress and pretending to be something you are not.

When you are learning to pass as a woman you should feel happy and fee to express yourself and explore you true being! Exude your sexuality and be more open with who you truly are!

If you want to pass as a woman and turn yourself into the ultra-femme, these are some things that you should avoid like the plague!


Cross Dressing No-Nos

Do not wear some cheap wig that has no style but big hair – you will be spotted a mile away and any gaggle of teenagers that passes by will burst into laughter.

Remember that cross dressing is NOT synonymous with looking like a hooker. Tight, sexy clothes have their place, but when beginning to cross dress its way too easy to cross the line into ridiculous.

Once you have that perfect outfit chosen, spend some time practicing in front of a mirror. You don't want to look awkward or nervous in public as these are dead give aways.

Don't cake on the makeup to hide your face! Spend some money on quality makeup and consider consulting with a makeup artist to find shades that are perfect for you and your individual skin tone. There are thousands of options for a reason!

Don't walk in those heals like a bowlegged bandit. Heals are tricky business and I know many genetic woman that will sprain their ankles if they attempt to wear them. They take some practice and getting used to. If you want to pass as a woman in heals, PRACTICE!

Avoid talking like the “gay guy” from Will & Grace. You may need time to raise your voice and I've found that singing to tunes sung by women is a good start without taking voice lessons. Avoid caffeine and other foods that make your vocal cords constrict.

Don't dress in clothes that are meant for someone 20 years younger – or that went out of style 20 years ago. You will have much more success at passing as a woman if you shop where genetic women shop. The juniors section may look sexy, but if you are pushing 50, no one will take you seriously if you wear juniors clothing.   

These are just a few things to avoid when learning to cross dress. There is so much more to learn about cross dressing!


Learn how to pass as a woman today.


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Your Thoughts on Cross Dressing Mistakes

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    • profile image

      Barry 

      2 years ago

      I like to dress as a woman

    • profile image

      good girl 2014 

      4 years ago

      hi am full time girl have t-Girl long time my wife and mother-In-Law are very goodto me only dress in skirt blouse cardigan have wear nice wool coat I have been wearing my wife New camel coat she say look bater on me then her so she will not wear it now I have it wear when go out with my mother-in-Law has MY wife work 12 hours day six day from 11am-11pm so my mother-in-Law take care of me she will not let me stay up late have to be bath dress in nightdress cardigan but to bed at 7pm so have be good girl for then thay do not like me being naughty girl as not been very well for few mouth and have go back in hospital for test that is why are good to my you need wear cardigan all and bed cardigan to would like getting cold. so do you think ok to has thank if can stay up bid later I did has my mother-in-Law Few's weeks she toll me no you so would like to up set then if I have in bed at 7pm will be good girl. would to not what you think if you can me we had lovely day when shopping got me nice nightdress cardigan to wear when got back in hospital thank you kind regards Elsie Ann

    • profile image

      john taylor 5150 

      4 years ago

      I kive in Houston,. needing a cool friend to help me dress up,. I got the cost and bill. ill buy u make up too n clothes,. just wany to look right and be with a hot same person... I am jon.

    • profile image

      Kathleed D.  

      7 years ago

      My boyfriend would never want to be referred to as a crossdresser, but he will wear some things for me, as long as they don't show under his guy clothes. I got him to take me on a trip to the Dominican Republic where he wore panties every day. It was awesome! He will wear a bra for me too, as long as a jacket covers it. I 've gotten him in pantyhose, control panties, a girdle,and some other fun things We enjoy shopping together as well-usually at Lane Bryant. I don't think he could ever pass as a woman, but I enjoyed reading your hub.

    • Georgiakevin profile image

      Georgiakevin 

      7 years ago from Central Georgia

      Miss Jessica I haven't connected with you in a while. Hope you had a wonderful year so far!. Merry Christmas!

    • profile image

      sissychuck44 

      8 years ago

      thanks for the great hub!!

    • profile image

      Val Marks 

      8 years ago

      Just stumbled across your hub and wanted to comment that the information and advice is extremely good and helpful.

      I have bookmarked the site and will come back and visit regularly.

      Cross dressers try to pass as women but without good help and advice they have to suffer the humiliation of the trial and error stage. Good help avoids this stage.

      Keep up the good work.

    • profile image

      pauls_boat 

      8 years ago

      i belive that a crossdresser is a person who wants to wear the clothing of the opersit sex but does not want to appear as the opersit sex, a transvestite is some one who wants to wear clothing of the opersit sex and also wants to be accepted as the opersit sex.

      i am a crossdresser i prefer to wear skirts or dresses but i do not want to be taken as a female, most of the crossdressers i know are the same they love the clothing and would like to be able to go out wearing it but they don't want to be took as the opersit sex.

      i accept that most people belive that all crossdressers are men but in truth it is the opersit most crossdressers are female it is just that when a female wears male clothing no one seams to be bothered but when a man wears the clothing of a female then he is pointed out as a crossdresser or said to be gay.

      to be gay is better accepted then to be a crossdresser.

    • Georgiakevin profile image

      Georgiakevin 

      8 years ago from Central Georgia

      This is a wonderful hub full of good advice not just for transvestites but for transsexuals as well!

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