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Fashion Stages of a Crossdresser

Fashion Stages of a Crossdresser

It is widely reported that irrespective of what physical age a crossdresser begins dressing, they will invariably go through different fashion stages which explains the all too apparent look of short skirts and tight blouses seen on many crossdressers.  They’ll  follow a fashion development pathway that is typically comparable to that of a normal woman but without the influence of feminine socialization experienced by natal women.

Initially, the cross-dresser sees cross-dressing as a form of ‘adult’ play and will want to dress up in the same way that a young girl will utilize costumes to create fantasy characters and will attempt to transform himself into a stereotypical, media-created fantasy woman often using themed costumes,  for example, a school girl, a maid, or a nurse  Often it is centered on lingerie items which is where most crossdressers begin experimentation.

Although I have drawn on the dialogue of Catie Maye in her book, “Men Can Wear Dresses Too”, available through Amazon, for this article, I’ve used the input from the many respondents on Sister House and tempered by my own 60 plus years of crossdressing. It seems to fit.

fashion stages - stage 1

Stage 1: The first stage occurs with those who are new to cross-dressing or those who have recently discovered a desire for cross-dressing. It is asserted that when a man first recognizes that he wants to dress in women’s clothing he will invariably select clothes that he, himself, would fantasize seeing women wear. The outfits he chooses will typically be drawn from his personal experiences of erotic images of women, as seen in magazines and on television and on film. (Of course, these erotic images of scantily clad women are created to feed into the male fantasy, and generally do not represent what most women would see as appealing, erotic, or comfortable.)   The selection of erotic or fetish clothing will create in the crossdresser’s mind a perception of increased femininity— with it being frilly and otherwise pretty— as well as arousal, supporting the crossdresser’s sexual connection to cross-dressing.  This is known at “fetish dressing” and probably represents from 40-60% of the MtF crossdressing population.

fashion stages - stage 2


Stage 2:  After a period of time the cross-dresser no longer obtains complete satisfaction with this singular form of sexual cross-dressing and begins to expand his wardrobe to encompass normal wear in an effort to create a more ‘normal’ opposite gender look. However, the desire to continue to encompass erotic elements of stereotypical opposite gender fantasy will see outfits similar to that that you would expect to find on teenage girls. The choice of clothing will be feminine but risqué; it will be largely socially acceptable, yet challenging.

During this phase, the cross-dresser will gain confidence in the selection of opposite gender clothing and may begin to develop a specific style or character.  As the cross-dresser matures, he will select clothes that better suit his own physical shape and the female character he has adopted, allowing him to more realistically ‘pass’ as a woman. ‘Passing’ has replaced sexual arousal in terms of importance, and the cross-dresser will select outfits that are more likely to be selected by a typical woman. Whist there may remain some sexual arousal resulting from cross-dressing this will not, as before, form the primary need or desire. We estimate 10-20% of the crossdressing population is in stage 2.

fashion stages - stage 3

Stage 3:  As the cross-dresser further grows in confidence and begins to better understand the character of his developing female alter ego he will attempt to reflect ‘her’ in the style and choice of clothes, much in the same way as a woman in her twenties would, who has come through turbulent teenage years of body change and hormonal upheaval and has now found a particular lifestyle and character. Our cross-dresser also now understands ‘his look’ and the clothes that present him in the best female form. This period of development also, for the first time, sees our cross-dresser concerned about actually being able to ‘pass’ as a woman, a concept considered important for most who cross-dress. Clothes are chosen and carefully coordinated in order to promote and enhance the figure and style choice. Skirts are worn less and certainly for going out tend to be replaced with well-fitting dresses of good quality, accompanied by raised but not high heels. The cross-dresser will purchase a better quality wig, and the length will shorten to shoulder length. Make-up will be carefully applied to achieve a specific look in tune with the character required.

fshion stages - stage 4

Stage 4: The last stage of transvestic development in fashion terms will see the cross-dresser want to acquire clothes that are of better quality and are a better fit.  She has reached his maximum earnings potential and, therefore, has more disposable income to purchase designer labels, tailored garments, and/ or specialist transgender clothing. Hemlines will have dropped to just above the knee, and the cross-dresser will have a full range of shoes to match each outfit. Typically, skirts and tops will be tailored, and all clothes will be more restrained and stylish. The length of the wig will have shortened again to just above the shoulder, and the color will more reflect the true age of the wearer. Make-up will be selective and good quality, used to highlight eyes and lips. The cross-dresser in this final stage is not challenging society or seeking attention. He is happy in who he is and just wants to reflect that image with the clothes he wears.Each of these last two stages each represents from 5-10% of the crossdressing population

These fashion stages are not hard and fast lines as there is a greying of the lines between the stages. The lesson to be learned is that your fashion is likely to change with your growing maturity as a crossdresser. But unlike real women, you do not need to go from fabulous to frumpy. Our Stylish Crossdressers are but one example of women in the 50s to their 80s that still rock a dress. Follow me here on Tasi’s blog or on TG Forum for the latest in how to dress stylishly.

stylish crossdressers fashion stages

Stylish Crossdressers






Jennifer Ann Edwards says:

Yep…The article pretty much sums up what I went through.
Now in my 60’s i am very secure in my femininty.

Elizabeth G says:

This is spot on for me. At 53 I would put myself solidly in stage four, but I certainly progressed through the first three stages on my journey.

Rita Doyle says:

It describes very accurately the stages we as crossdressers go through. In my case I went to stage 4 very early, I was in my 30’s when I started to go out in public and blend in with the real female population, so I would pick my clothes very carefully after observing women who in my opinion dressed in good taste, including my wife. I wish I had kept those early photos of Rita that were destroyed in one of those self-purges..

Dr. Tim Byron says:

I think WE CD ers all have the same “story line “. Acquire /Hide /Purge…over & over & over. ..until one day, you say to yourself and others ( or if caught dressed )…that ‘s it….this is part of my life, & others need to know.
Please get back to me if you relate…

TB admin says:

TJ. The purge cycle is typical for many but certainly not all. It wasn’t for me. I never gave any thought to purging, but I am one heck of an Ebay shopper 🙂 I knew from the first instance when I was fully transformed in a transformation shop that there never would be a going back, for hell or high. That’s me though….Tasi

Dr. Tim Byron says:

THXS for your discussion. ..I guess,I was always “afraid ” of being. ..”found out “…I was a prominent member of the medical community in So. CA.I could not afford a “scandal ” by coming out, beyond Halloween nigh parties, & by the way, I never entered a “Dress up Contest ” that I didn’t Win. . . No one knew who I was! !
I have been out since the 1960’s & dressing from the late 1950’s. Was Army Medical Officer for 25 yrs. & a Chief, at the VA, 2O yrs. I had a lot to lose, if I came “out “. Now retired, I’m out & about. &by the way, married over 35 yrs. My wife and I go to lunch & has taken pics of me. I dress respectful of her. Recently moved to Seattle, Washington area & finding comfortable.
Enjoy being You! T.J.

andrina says:

If there’s a next stage it could be called “Trousers/Pants”
I work as an “escort” in London UK and of course that means that clients want me to dress stage 1 or 2 style.
However I am growing my hair out (I am 55) and slowly evolving a look for every day. I find a tunic or mini dress paired with leggings, palazzo pants or jeans with low heels, appropriately accessorised is a look which meets with approval from cisgender women of my own age.

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