Learn to Crossdress in 19 Steps

The first time a man puts on a dress he looks like – a man in a dress. In our minds we picture ourselves as dainty, feminine and gorgeous, but we’re actually a man caught wearing girl’s clothes. Looking good as a woman is a hard thing to do – just ask any lady who has spent an hour doing her hair and makeup!

If you’re just looking for some quick tips on what to wear the first time you cross dress then my previous article is the right place for you to start. If you want to look fabulous, and pass as a genetic woman – then read on!

There are seven aspects to looking great and passing as a genetic woman every time:

April Live Sessions - cdh
  1. Wearing clothes that make you look good
  2. Making sure your curves are in the right places
  3. Feminine body movement
  4. Hairstyle that feminizes your face
  5. Natural makeup
  6. A feminine voice
  7. Loving who you are as a woman

Do we want to look like men wearing dresses?

NO! If you’re like me, the image you hold of yourself is as a beautiful movie star, not a guy in drag. The truth is that we can all look and feel beautiful – but it takes some work. Over the next few weeks I’m going to share with you some of the secrets to looking like the woman you see inside – to cross dress for success.

If you’re eager to look fabulous today, I highly recommend Lucille’s Stepping Out Secrets. You’ll get all the tips and tricks you need to be the woman you are, and complete your male to female transformation! I used Lucille’s resources when I completed my transition many years ago, and she is the real thing!

Learn How to Crossdress

Learn How to Crossdress and Step Out

Before we get started though, I want to share with you the biggest mistake men make when they wear woman’s clothes. This is probably the number one reason why cross dressers fail to pass, and end up looking like a guy in drag instead of a passable woman.

Before I share it with you, think for a moment on how you picture yourself as a woman. Let me guess, high heels, short skirt, dramatic makeup and plunging neck line. Am I right?

En Femme Discover Woman Within

The biggest mistake the transgendered make is that:

When men cross dress they try to look like a whore

Not many woman would be caught dead wearing 6″ heels and a mini-skirt that barely covers their panties. Yet cross dressers try to dress like this – they’re dressing as their own fantasy girl. Take a tip from genetic woman – most of the time they are dressing for their girl friend, or to impress other woman. They are trying to out do other woman, not fulfill a man’s sexual fantasy.

Even if you’re lucky enough to have all the other attributes of a woman, if you dress like a whore you will stand out.

In the first lesson (coming next week), I will teach you how to wear clothes that make you look good, so you can cross dress with confidence.

More Articles by The Author

5 1 vote
Article Rating
Notify of
Inline Feedbacks
View all comments
12 years ago


I have been dressing in female clothes for years and the feeling is fantastic, a nice little black dress, tights, panties, bra, and heels, it is just a pity my wife does not like agree and join in my fun, woman are so lucky in the way they can dress, us men are so bloody drab, I am new to your site and it looks very helpfull will be back.

Love Wendy

Kelly Stevens
Kelly Stevens
12 years ago

You asked for tips on passing 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… Read more »

Priscilla Aguirre
Priscilla Aguirre
12 years ago

Thanks for the fine advice. Sofisticated, well explained and useful.
I can´t wait to go in public but have no company. Love to look younger than 60, but…
I can´t pierce my ears either and love big earrings.
First time at your website. I´ts fantastic
Thanks. Keep it up.

12 years ago

Do you have any tips for a guy thats 31 years young 6ft 4in weighs 225lbs and has a lot of tatoos. I embrace my manly side as well as my fem side. I already have my style down for my manly side. Now I gotta find a style that best suits me for my fem side. I like the Amy Winehouse look. What do you fabulous people think? Someone please help!

11 years ago

You got that one wrong. 🙂 For one thing, like someone mentioned previously, some of us don’t dress to pass, just because we like the clothes. Nevertheless, when I pictured myself as a woman, I was wearing a bridesmaid gown, bridal gown, or prom dress, or a knee length pleated skirt with modest heels (just a couple of inches), and a pretty blouse — and no stubble, pretty hair, etc.

Don’t get me wrong, I like your blog, thanks. If anyone out there wants to read my blog, I wouldn’t mind a visitor or two either, LOL.


11 years ago

Greetings to all I’m new to CDH and have read with joy all that I can. I have CD most of my life but tge demands of family and society it was always in private.but now that I’m 56 yrs.old and those demands are mostly gone I desire to become who I have always been on the outside.within has always been there.so can any one please help me with age appropriet tips on fashion and makeup.thanx all. Leona

11 years ago

Greetings to all.you have said to watch woman my age and style.I do and have learned so much.rihgt now for me the gresatest joy is allowing my dominate fem side to take from my male side those things that can make me undrestanding of who Leona is.slow prosess but one worth the wait.untill next time.Peace to all

11 years ago

hi. i am sorta new to cd. i have always been a closet cd and have never done it in public. i do have very hairy arms and legs (which i cant shave, because i deal with to many people at work). i have finally worked up the nerve to do it in public, what do u suggest to cover up my arms and legs (noting that it is summer and hot out). thank you~lisa

1 2 3 7
Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.