Learn to Crossdress in 19 Steps

Here is a Blast from the past from our site owner, Vanessa. Published originally on March 3, 2008


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:

Visit Transgender Heaven
  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?

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 Vanessa Law

View all articles by Vanessa Law
The following two tabs change content below.
I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

Latest posts by Vanessa Law (see all)

5 2 votes
Article Rating
Inline Feedbacks
View all comments
Fiona Adams
4 years ago

What you say is very true,just look at Girls who put images online most have dresses or tight short skirts heels and often the wrong wig or hair.
From the start i wore a pleated skirt i tried a tight short skirt which i bought from a store it looked good but i couldn’t ..at that time get the smooth flat front
As you say try cloths that you look good in and looks change with age so a reason to shop

Active Member
3 years ago

See I think I must be the misfit here. I like lookibg like a man in a dress look. For me, its easier and cheaper. Here is what I mean. I don’t have to buy make-up(don’t like it anyways), don’t need to buy breast forms or pads, no need for padded panties, and so on. I can just shop with my true body size, and I can keep my beard and chest hair. Like spring is just starting now and my spring/summer maxi dresses can come out again. Sure I get looks and hate talk when I’m in public, but… Read more »

Jeri Eddy
5 months ago

That’s so true. Every place I’ve looked for ideas on how to dress, they look like a tramp. Some were WAY too much makeup. I’m trying to pass as a woman, not be a tramp. For me it’s the thrill of being a man in public, dressed as a woman and nobody else knows.

Active Member
5 months ago

@Vanessa Law This article was written in 2009. Since then, some things have changed. One of the comments mentioned removing hair on arms and legs.
Since 2009, many males have gotten tattoos. Lots of men have removed their hair because of this. It can at least be used as excuse even if you don’t have any tattoos – yet.

Michelle Nelson
Active Member
5 months ago

I remember when I came this realization myself. I wanted to dress like a teenage girl. But I’m not a teenager I’m middle aged. So I started dressing my age. I looked at how my wife dressed and I mirrored her. I ended up with what I’ve been told by some ladies on here is a very “mom appropriate style” and I’m not offended to hear that. I realized a woman my age would probably be a mom and as such I that’s how I should look. I’ve been very happy with my results. I feel like I’m very passable… Read more »

M Murph
5 months ago

Though I would truly love to have a more feminine body, and that will never happen, I’m content with just underdressing. I do wear panties24/7, a bra at least 6 days with forms every week along with other feminine under garments and have done so for many years. Super fortunate that my wife is very, very excepting. I’m at a happy place and supportive of anyone that can enjoy dressing no matter at what level and feel sorry for those that are in a DADT relationship. CDing is such a harmless thing and life is short so happy dressing. From… Read more »

Gail Bingyi
Active Member
4 months ago

Hi I do agree with what you say and I think that there is a difference within the crossdressing community, there are those who see cross dressing as a sexual fantasy and in their minds I think they want to be that glamorous sexual object of desire, while others of us are more interested in being a woman and being accepted as such by other women and men around us. This is why we spend so much time watching how GG’s dress, walk and talk and then doing our best to imitate them. Acceptance is our goal. That is not… Read more »

Jamie Gurl
2 months ago

informative and helpful

Jane Millane
Active Member
28 days ago

I think often when someone is starting with cd they imagine themselves as a certain type of woman, beautiful sexy etc. I think it’s best to dress your age as a woman. I think we need to be realistic and take it 1 step at a time. This is the second time l have tried cd, last time l used to take the dog for a walk just after dark. My wife applies my make-up and it looks pretty good. I am still in the closet however when the weather warms up my wife and l intend on going on… Read more »

1 5 6 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?