How to Crossdress to Impress – Part 1

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Learn how to crossdress to impress can be tricky but here is some help!

So you want to learn how to crossdress?

Do you want to pass as a beautiful sexy woman you always dreamed of? Truth is you CAN! You just have to learn how to crossdress to impress!

Crossdressing is not the same for everyone so it would be unfair to classify all crossdresers into one category and assume they all are seeking the same level of information when it comes to learning all the do’s and don’ts of the trade.

I am going to cover some of the the main topics related to learning how to crossdress, however if any of the sections do not float your boat, just disregard that particular section and move on to the on that charms you.

If you want to look stunning and be able to pass as a genetic woman there are primarily 8 aspects to looking hot and magnificent every time.
They are:

1. Wear clothes that make you look good and balance your body.
2. Make sure your curves are in the right places.
3. Master feminine body movements and body image.
4. Wear wigs or hairstyles that suit your face and feminize your face.
5. Wear the proper natural looking makeup and don’t overdo it.
6. Work on developing your feminine voice and pick a femme name.
7. Love who you are as a feminine being and enjoy the woman in you.
8. Master the art of hiding your manhood. Also known as tucking.

All young girls’ beauty lessons and training start at a very early age, usually around kindergarten age and by her teen years she will alreadyhow to crossdress tips have gone through hundreds or even thousands of hours going through trials and errors, practicing and experimenting.

Mothers will teach their daughters what to wear, how to dress, how to behave and how to look after their faces and skins.

Older sisters teach their younger sisters how to add volume to their lifeless hairs and how to talk to guys. Teenaged girls teach each other and experiment with eyeliner, mascara, nail polish, jewelries, hemlines, hosieries and high heels. Therefore, many people believe if a man was not brought up as a female, he would never be able to join the realm of womanhood since femininity is a very complicated thing.

Don’t be fooled

It would be foolish for us men to assume that mastering the art of crossdressing would be a quick and effortless endeavor.
Fortunately you have come to the right place for all your advanced education and training when it comes to passing as the woman you want to be.
Acquiring such skills can bring you great personal satisfaction but is also absolutely necessary for crossdressers who want to avoid attracting too much attention while crossdressed out in public.

The last thing we men want is to look alike a dude in a dress. Learning how to crossdress involves many levels of learning, adapting and practicing. Patience and dedication are paramount if you want to become an ultra crossdresser.
Crossdressing can be a hard act to master perfectly first, but trustworthy advice, patience, persistence as well as lots of practice will get you there.
Just ask any woman who has spent an hour doing her hair and makeup.
Women have years of practice in all things feminine so don’t expect to master the art of womanhood in a week or a month.

It starts in your mind

Mastering the art of crossdressing I believe starts in your very own mind.
The emotional and psychological element of being a woman is also very important. After you have mastered a successful female outer image, you must also learn to develop a successful female inner image which is equally important. The key is that you must convince yourself that you are a woman and think and feel like a woman. Remember, confidence is extremely important.
Have you ever heard of the laws of attraction? The law of attraction reveals that you attract what you focus on.
I can assure you that if you start seeing yourself as a woman and develop a more feminine mindset in your life, at least on a part time basis, you are bound to be on the right track.

The seven primary features of learning how to crossdress as I outlined above are a solid starting point for any crossdresser to embrace if he desires to go full circle, however there are many little tricks of the trade and little underground tips you must learn and master if you want to begin looking and feeling like the woman you see inside.

How do you see yourself?

Before I get into the hardcore stuff, let me ask you; how you see yourself as a woman?

If I had to guess, probably high heels, short skirt, intense makeup and a curvy bodacious body? There aren’t many women who would be caught wearing 6 inch heels; mini skirt that barely covers their panties.
Yet many crossdressers try to dress like a slut, sort of like their own fantasy girl.

It would serve us crossdressers well to embrace some valuable tips from genetic woman; most of the time they are dressing for their girlfriends, impress other women or trying to outshine other women.

They are not trying to fulfill men’s sexual fantasies.
Even if you’re lucky enough to possess all the other feminine attributes of a woman, if you dress like a whore you will stand out for sure.

Quick Tips Every Crossdresser Should be Mindful of

Do not wear some cheap wig that has no style but big hair as you will most likely be spotted a mile away. Last thing you want is to look a clown in the circus.
Remember that cross dressing is NOT identical with looking like a hooker.
Tight, sexy clothes have their place, but when beginning to cross-dress it’s too easy to cross the line into outrageous and inappropriate.
Once you have chosen the perfect outfit, spend some time practicing in front of a mirror. You don’t want to look awkward or nervous in public as these would be dead giveaways.

Don’t cake on the makeup to try to hide your masculine facial features! Your goal when applying makeup is not to try to hide every imperfection, nor is it to create a dramatically different image of yourself, one other than what you see in the mirror.
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. Make up companies don’t make thousands of varieties for no reason. You should approach makeup with a light touch, intent on highlighting your best features and drawing attention away from those that aren’t as flattering. I highly recommend a great book by Kevyn Aucoin, Making Fasces. This great makeup guide will take your makeup artistry.

Don’t walk in those high heels like a bowlegged bandit.
Heels are tricky business and I know many genetic women that will sprain their ankles if they attempt to wear them. It will take some practice to master walking on high heels. Start with heels under 3 inches and work your way up to those towering 5 inch beauties. And don’t forget, PRACTICE, PRACTICE and PRACTICE!

Avoid talking like the “gay guy” from Will & Grace. You will need time to train your voice in order to raise it and sound feminine. Singing to tunes sung by women is a good start without taking voice lessons. Avoid too much caffeine and other foods that make your vocal cords constrict. There are also various online resources in the form of CD and DVD lessons that will greatly speed up you voice training endeavors. Here is a voice feminization program that has a proven track record you might want to try.

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 department may look sexy and tempting, but if you are pushing 50, no one will take you seriously if you wear junior’s fashions especially out in public places.

Next time, Marcy will cover all the really juicy stuff you must know to crossdress to impress.


About the Author:

Hi, I’m Marcy Simpson, the founder and creator of Crossdresser Society. I have been a crossdresser for over 25 years and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.


  1. Avatar
    Annie  March 14, 2014

    Hi Marcy thank you for your story it gives me courage to continue on my journey. as many have said before my fascination with the look and feel of feminine clothes started when i was just seven years old . slipping on a pair of moms panties was as addicting as any drug i could imagine. My addiction grew as i became older adding her slip with moms high heels was pure delight. It took many years and a few drinks before i mustered to courage to shop for some intimate under garments for my self, Century 21 was my first store and as i went to pay of MY Panties and Camisole (how thrilling it is to say MY) the young lady at the register guessing that they were for me, smiled and said that the color was perfect for me (mocha). I turned three shades of red i just stammered a thank you and rushed out of the store. Funny but I never went back to that store. i have started shopping regularly in Burlington’s and several other stores at Garden City Mall and it gets more comfortable each time finding the right fit is a challenge without trying on things at the store. But i love shopping so much i just return the items that don’t fit and can shop till i drop all over again. I try to practice walking in my heels as often as i can steal a few precious moments alone (sigh) . I adore walking in my 3″ heels with stockings and skirt on !!! Well thank you for listening to my story TTFN
    PS i just decided to return to Century 21 today to celebrate my Feminine Freedom !!!

    • Marcy
      Marcy  March 15, 2014

      Thank you Annie for your lovely comment and congrats!

  2. Avatar
    Keri Cantwell  October 10, 2014

    Hi Marcy,

    I love this article! Particularly love number 4 to always look stunning- not over doing the makeup. I feel like this is such an easy think to over-do. Transforming into this beautiful woman is so exciting that it becomes so easy to just layer on foundation, eyeliner, lipstick, and eye shadow. That is why I try to provide a lot of make-up tips to help avoid this common mistake. I also really enjoyed your segment about how important it is to have a feminine mindset. Thanks for your great articles Marcy.

    Keri from

  3. Avatar
    "Paula"  November 30, 2014

    I have just told my wife I’m a crossdresser and so far she has been great.She says she doesn’t want to see me dressed but the fact she listened and understood is such a wait off my shoulders.Hopefully in time she will take me shopping and dress me as a nice woman like she is

  4. Avatar
    Royal Dipa  December 8, 2014

    for walk gently like a woman High is best , for automatically curve your hip but after best practices

  5. Avatar
    Lily Smith  April 27, 2015

    Hey Marcy, The only problem I seem to find on many of the crossdresser sites out there is finding a bra that truely fits. So many times I see a beautiful bra yet it is ment for someone that is a b-cup or larger. It would be nice to find a site that has aa-cups. As genetics prove not every woman has a huge bust.


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