How has your dressing evolved over the years?

I've been thinking about my crossdressing lately and how my attitude towards it has changed in the past decade or so when I began to dress as a girl. Right now, I dress up as the whole thing; wig, makeup, bras, dresses, hosiery, skirts, and now I really want to start wearing earrings. I've come to realize it's changed so much since then. I began by putting on a bit on lipstick. I felt like a lady while wearing lipstick! Now, I've always been fascinated by hair, so I've always liked wigs. No matter what, I've always wanted to wear wigs all my life, and various types of wigs such as clown wigs or those old wigs worn by English politicians. But what always stuck out to me were the long feminine wigs. After that, I started wearing bras and until mid-high school, I started dressing up completely. I find it interesting how my approach to crossdressing has changed over the years.

How about you? Has your dressing evolved since you began?

When a friend was helping me discover myself two years ago, it was "definitely just about the clothes, they make me feel good" and there was no way I'd ever get invovled in shoes or makeup, I just didn't get it, didn't see any point.

Now I own three pairs of shoes, a limited set of makeup in black and red (to match my current limited red/black/white wardrobe) and a pair of chicken fillets. I'm keen to get a wig, at least bleach my leg and arm hairs, although Mrs Flowers is not keen that I do either of those, despite her highly enthusiastic acceptance of my dressing generally.

Over the years means 5+ since I started this interesting journey. My dressing has evolved from total dressing with all the accessories to doing the same thing with much better taste and a very large overflowing wardrobe. Along the way my knowledge of this side of me, similar others and the various lifestyles has progressed to a fairly good level of knowledge and some interesting experiences. My daily routines have also changed from in and out of the bathroom and shaving when I want or absolutely need it, to a much more elaborate process all geared toward my femme side. I have pierced ears and am more than halfway into facial hair removal by electrolysis. I have gone from looking for friends with whom I can go out and enjoy now en femme what I once and still do enjoy doing in male mode. I have found some good friends, most from this site, and now also have some GG friends. In fact, one GG friend is taking me and a couple of her GG friends to the San Francisco Ballet this Saturday for my birthday. So, yes, I and my life style have changed and progressed "over the years". Now, I do not see any light at the end of the tunnel, but then, I don't think that I am in a tunnel, at least not yet.

Hi,

I like the pic you have of the peep shoes, the older style & they look nice,

I cant claim to being a dresser , yet i had been dressed by my Mum & another women for a end of year do. & that was good & fun in front of over 80 people & my Mum.

My style has changed over the last 16 years, because along the way i joined two period groups so the clothes are quite different, so if you like from boy clothes to womens clothes to period wear & garb, & its lovely to be dressed differently & be seen by many people a little different yet still dressing.

...noeleena...

I have to say that I have evolved in my dressing from outrageous to mainstream and a little on the conservative side. Back in my early years, I had a lust for the trampy hoochie-momma look, but now at 50+, I try to present a more age appropriate and fashion forward look. I do have to say that heels of 5" or less are a whole lot more comfy than mega platforms!

I was well closeted and minimalist for many years, then I started to buy things and would purge. About 5 or 6 years ago I decided to embrace this side of me and accept that it will never go away. So yes, it has changed over the years and I have evolved as a CD/TG whatever I am. Today it is part of who I am and I embrace my 'Kaz' side every day. I will never transition, but I want to totally explore this part of my life.

Fashion/clothing-wise, I dress age inappropriatley! Although I am exploring more conservative attire for the older woman! I just love short skirts and the way they feel!

Hi Katie, I like to think that it has as I have three closets full of clothes and over
125 pairs of shoes and about 30 wigs I can dress for any style, mode or event
I have perfected my dressing and look to be as feminine as I can.

Hmmm How have I evolved? Well in the last three years I went from No one knowing to eight people that know, well that I know of anyway.
I pluck my eyebrows, shave everything, own more tops then shirts now, Have gone out a number of times. Not many but getting better.

Oh I have accepted the fact that I am a crossdresser, however I am thinking I may be more then a crossdresser, possibly TG as I really want to present as a woman more and more now then I thought I would, what holds me back is my family, not using them as an excuse, just afraid of what could potentially happen if I told them I want to present as a woman.

I want to have laser hair removal, I want to develop my own real breasts and appear more female then male. So I am still progressing further then I thought still.

Kaz's situation is similar to my own. I was deeply closeted and repressed for much of my life. I had once gotten a glimpse of myself, wearing my ex wife's wig...and was surprised by the femininity I saw in myself. I hadn't considered it possible. But I was certain that someone of my stature (6'2") could never present convincingly as a woman, so I put it out of my conscious thought.

Later, after a painful divorce and some extensive counseling, I finally came to grips with this part of myself, and was able to tell my then GF ( now my wife of 13 years). With that road block removed, I started exploring...buying a few items, dabbling with make up and dressing a little around home, but never really having a coordinated look. In the process I discovered that while I'll never be a great beauty, or even passable, I can be presentable and comfortable in public as a woman. The break through came when I finally sprung for a wig - at that point, it seems that the whole thing came together. Since then, I've gone public on a daily basis, grown increasingly comfortable acknowledging this part of myself to family, friends and neighbors. So, its been quite a rapid evolution in recent years.

Hi Katie, being one of the older girls I suppressed the CDing urges for a very long time. There was no internet and CD's were considered mentally ill (can you imagine living with that thought?). I did underdress mostly from time to time. Halloween was the only time I dressed fully for the last 5 years. This year at Halloween I added a wig and makeup, and bang! I realized this was me, so I embraced it never to look back again. Once I embraced it all the floodgates opened, depression and anger left and I was truly happy for the first time in my life. Now the feelings I had as never fitting in as a kid make complete sense.

After the "reawakening".... And nearly a decade of evolving I think I've peaked and now devolving.... And I'm ok with it. And really don't care.... I've go so many things on my plate and I'm enjoying life.... Independent of the clothing I wear! Frankly given the choice... I'd rather go play ice hockey or go do something with the family.

I began at about age 7 and had my first complete outfit (hair and makeup as well) when I was about 18. I looked like a tramp. All I wanted was sexy, revealing clothes that made me feel hot. A big part of it was the sexual stimulation I would get from dressing.
Over the years I feel I've developed into a woman. I no longer dream of being on the cover of Playboy or modeling lingerie in some catalog. Now I just want to be me, be able to dress in what makes me feel comfortable and go out in the world expressing the woman that's always been inside.
I no longer dress to be sexy, I dress to be me. If there was one thing that I could ask for, it would be to go unnoticed, to blend in, to be just another woman in the world.

Started off with one or two items and stayed that way for years. A little more involved with a wig and makeup in my 20/s. Started being OK with it when I started coming here. Now I'm out to several people and actually am beginning to enjoy this part of my life!

Hmm. Briefly, as a toddler my mom put me in my sister's 'hand me down' dresses, supposedly to save money on my boy clothes. But that didnt explain why she didn't get my hair cut, and tended to style it like a girls. That stopped at 3 y/o. At 6, an older boy dressed me in his sister's juvenile outfits so he could have sex with me; but as he was also my only source of physical affection, that link made me want to interact with him, despite the negative aspects of the relationship. So, I developed a penchant for early teen girl clothing through those years, and still prefer styles appropriate to someone of young teen age years. Plain tops, plaid skirts, sailor dresses, mary jane shoes, long straight hair. ETc.. I guess I didn't really evolve much, did I.

I've kinda gone from the all girl look to the all girl natural look. I learned a lot of womanly short cuts along the way, mostly from doing. The thing I've learned the most is that it's the person who exudes the beauty not the appearance.:)

I finaly stopped purging .Pretty well have 1 of everthing these days

Total evolution! I remember the beginning, just lingerie. And then the gradual but constant progression over the years. Now I just can wear undies. If I can't go all the way I'd rather not go at all. It's like the pink fog gets me and I am in it for days at a time. I like my guy life a lot so I pick when I want him to disappear and her to appear. Then when she is here I never want to go back to him. Confusing? Such is my life. Cheers

I started using my aunties clothes, and that being enough for me. I fantaziced about having a full on outfit with make up and wig for all my teenage years, and until recently i now have my own wig, started learning how to use make up and while it took me a while, i gotta say it was worth it.

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Originally Posted by Katiegal

How has your dressing evolved over the years?

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[SIZE="2"]When I began, I didn’t go “all the way,” for fear of where this was leading me, but I soon took the plunge (out of curiosity) and dressed up COMPLETELY. These days, half measures are no good – it’s either everything or nothing, something I never could have dreamed of in my youth. This makes me a transvestite, and not just a crossdresser, since there is a definite change taking place each time I dress – my personality has evolved over the years, and I have managed to shake off the negative aspects of masculinity, modifying my “self” for the better. It was always there, of course – I just let it out to play. Evolution is a fact. I changed before my astonished eyes, and I continue to do so…
:battingeyelashes:[/SIZE]

Dressing used to be something I did once in a while when I found myself with free time, and now I actively free up time for more dressing. It's less of a sexual thing now than it once was. Besides that, I have gotten a lot more 'serious' with my fashion choices, gravitating towards the everyday woman look rather than the VS model. I dress more often and more completely than I set out to at first, but still find myself wanting more. At the same time, I find that I enjoy getting femmed up more and more. I don't think I will ever be able to manage full time, but as close to that as possible is where I'm heading evolution-wise.

I started playing with womens clothing when I was around 6 years old, how have I evolved over time? Well I started out in the bathroom hamper, trying everything my mother and sister put in it that didn't fall off my skinny little body. From that I started hiding "found clothes" in the back of our old wooden shed, these came from rag bags, or werever I could find them. Not much into style, just what I could get my hands on. By high school, I was back in to mom's stuff, sister having gotten married and moved off with the good stuff.
Buy the time I was out of school, and the service, I got married the first time and started buying at thirty stores, learned a lot about clothes, during that time, but the marriage didn't last so I purged for a few years.
Got remarried, and the desire to dress came back stronger than ever, so I told my wife, she started shopping with me, and for me, and teaching me about make up, and back then, when I had long hair, how to set and style it in femininene way. That was 40 years ago, today I've got a very large wardrobe, 3 to 4 times larger than my mens wardrobe, I dress more days than I don't, and I feel like I've gotten as good at it as I am ever gone to get. But in all of those years, I've still never had any desire to leave my closet, it has everything I want.
Tina B.

How have I evolved over the years is a question I cannot really answer with any detail of accuracy. It has been going on for so very long, fifty years out on the streets in fact. ( If only there had been the digital cameras then, now I have only two photos of me out there. Black and white they are ). At that time I probably needed my head seen to, to be daring enough to be out then but I had the youth and the confidence and I was out there.
I remember someone who broke a fairly high heel when she was ou one evening. A police car stopped to offer help but she sort of understandably ran. Not a thing to do in a one heel outfit. I later heard that her father resigned his job as bank manager when the story came out, as it was bound to do.
Anyway, I felt I belonged out there. Had it existed as common knowledge then I may well have changed, but I did not and therefore I am a plain CD. That part did not therefore evolve.
So to the style, originally demure as fashion demanded. Skirts long, just above the ankle. Hair styles have not changed that much for me and I have always preferred the blouse/pulli tops. I went with the min when it arrived, wholeheartedly but never with the maxi after that. Underwear is a whole different story but true to trad I used to favour black/red. Now I seem to have a thing about blue ! It suits my summer tan.
Makeup has always been minimal, hair attention variable but most always blonde ande never black, shoes I used to love dearly but now they are just forwalking. Jewelry came and went, except for the wrist metal bangles, they stayed.
Age appropriate - do not be daft. Future prospects ; diminishing.
~S~

I started off wearing prom and bridesmaids dresses when I was young. In my 20's I had a big ball gown made it looks like something from Gone With The Wind with long sleeves and zipped up high and tight in the back, its great for halloween or something like that. Now I still like to go with the formal look, I've tried slacks with animal print shirts with heels, scarves, nice coat and all the other accessories and it feels pretty darn good.

My evolving came quite recently.....about a year ago. All my life, I had strictly been an 'underwear' CDer. Meaning, I never wore anything except panties, garter belts, stockings etc. And my desire to dress was of a sexual nature.

About a year ago, that all changed....practically overnight. I now dress fully.....wig, skirts, blouses, shoes. I'm trying very hard to develop my skills at applying makeup. And I also no longer dress for sexual purposes. I feel THAT is indeed 'evolvement'. And, perhaps late-blooming feminine maturity.

I started off pretty young, (about 4), when I was fascinated with stiletto heels and stockings, and that has always been at the core of my CDing. When I was in my teens I got more into tights, panties and bras. I would wear a dress as and when I could get my hands on one, then kind of stopped CDing until I was into my 30's, when I started wearing stockings and shoes again. However over the last 10 years I have really gotten into the clothing, make up and being en femme. This was mainly due to a woman at work, who despite her age, looked great in a skirt, wore heels and had the legs to go with it. She just looked so good that I wanted/needed to see how it felt to be dressed like that. (It feels great by the way). Although I don't have a particularly female figure, by selecting appropriate clothing, and being pretty good with make up, I think I make a pretty good job of passing as female. The only down side is I generally now don't get en femme without doing my make up first, which has at times put me off, even though I have been looking forward to it all day. I will often wear a pair of heels about the house in drab, just for the pleasure of walking in heels though.

I am beginning to pick up on a theme here. I started much the same way as alot of you, at a young age it was quick and sexual. Now that I have gotten older it has become a comfort zone that is actually less sexual than male mode. I think my feelings about how I view it have evolved more than my look or what I like to wear. I have settled on my style though, instead of random outfits.

Like many I've been cross dressing most of my life. Now when I dress I like to go out in public and spend time as Joanne. Going out and doing normal things like shopping, dining, going to the movies means I have to blend. I try to dress like other 50 year old women I see but maybe a little bit more put together and a little bit prettier.

My dressing has evolved along very similar to paths to some of the other ladies.

I recently described in another thread when I acquired my first women's clothing at around age 15 (before then I would experiment with my Mom's stuff). I would say all through my adolescent life was an experimental phase. I didn't really know what I was doing or what I wanted. I just knew that sometimes I felt like I should be a girl and wearing feminine things was my only outlet.

In college I finally started buying my own clothing, but it was always lingerie. For the longest time I was just very content to wear a pair of panties. Then I added bras, stockings, etc. While I was still in college I began experimenting with makeup (just a tube of lipstick) and suddenly found my obsession for shoes. At that time I was still finding myself and wanted the sexiest, most extravegant pairs I could find (think stilletos, platforms, and thigh high boots).

I went through two purges. One right after I graduated from college and the other a couple years after my wife and I got married. After my second purge I stopped dressing and tried to deny who I truly was for about 3 years. Then after a lot of inner reflection I finally accepted myself for who I am and started buying things and dressing again. At this point in my life however my dressing really blossomed.

I don't know what the reasons were but ever since then I have no longer been content to just wear a pair panties or just some lipstick. I bought a wig, started buying real makeup (i.e. not cheap, mail order stuff), perfume, jewelry, and accessories. I started buying age appropriate clothing and shoes (no more stilletos). Then I went out en femme for the first time and I loved it. It had been an urge growing inside me (and strangely not an urge I had when I was younger and just hanging out in my apartment with a pair of panties on).

At this point in my life it isn't about dressing anymore, it's about being a woman. I never underdress and I don't lounge around the house in a pair of panties anymore (even when I have the house to myself). I'm at a point in my life now that if I can't be a "woman" (i.e. makeup, hair, clothing, accessories, etc.) and go out en femme I don't bother.

I think I was more fetish to start. Heels and stockings and short skirts. I did not care about my upper half. Then it evolved into a "look" of a clubbing 20-30 year old. Now I am a nicely dressed, upper end but still sexy not conservative woman in middle age...usually. :)

Complete look, head ti toe.

My experience started before I was 10 yeas old and now I am in my 60's, it started with just stockings and panties, progressed to full transformation when I was in my early 20's then nothing for 14 yeas then progressively from shoes to full transformation, then nothing until I was in my mid 50's. Now I am married to the only person who knows about Kathryn and is totally supportive and I dress completely head to toe when I can, go out and mingle as and when I can.
My wife says that because I am a full blown Gemini it is like living with 4 different people sometimes. But she says it with a smile mostly.
I hope this answers your question. :battingeyelashes::):hugs:
Kathryn xx

I'm strictly closet, and absolutely adore stockings and garters, not so much of the other femme stuff. But it's kind of hard to say where the evolution began. When I was for or five years old, my mother's bridge club would come to the house dressed to the nines in seamed stockings and heels. In hot weather, they would often raise their skirts and expose stocking tops, garters and straps and bare thigh. I wondered where those straps went. But I didn't get to wear things like that, and really wanted to try them out; even then they sensous and tantalizing. I started by collecting and trying on laddered stockings from the trash. Of course, they were very long for a five year old, and I've always loved my stockings nice and long. I pulled the stockings up my legs and held them up nice and tightly. I absolutely loved the unique feeling. At first, I had no garters, and could only hold the stockings up. But then I found in our attic a box of discarded clothing which included a couple of tattered open girdles. They must have been for young girls, because they sort of fit me. I excitedly put on the stockings, and then had the most difficult time figuring out how to attach the garters. When I finally succeeded, the long stockings were very loose, and i had to struggle bunching them up to garter them snugly. i was in seventh heaven.
The fascination with stockings and garters has stayed with me all my life. It's evolved through all kinds of gartered garments, fishnets, lacetops, seams and seamless, and you name it. I still love to wear stockings and garters

It's an interesting question and I can fully understand just about all of the replies so far. With myself, it was initially a fascination with underwear - I loved the immensly varied range of female underwear, and having had a relationship with an older woman (while in in my teens) who dressed to tease just increased my fascination. I started off with panties, then suspender belts and stockings, then bras too. Basically I dressed in stuff that I wanted my next girlfriend to wear.............

Since joining this website I've progressed dramatically, the underwear (whilst still very important) is almost secondary to the 'full look', without the infomation I've found here I would never have worn a pair of heels, a swing dress, pantyhose/tights, and god forbid - make up.

It used to be a very sexual thing with the underwear, now it's a 'look female' thing. I'm so used to seeing myself in the mirror with shoulder length blond hair and red lipstick, that if my landlady turned up for an unexpected visit I would no longer know how to present myself.

My weekly wash is one for work clothes, one for girl clothes (how do we use so many pairs of panties?) and nighties

So, in answer to you question, I've gone from panties to dresses, shoes, lingerie, make up, wigs and shapewear (Jees, do I need to get a kind of life?)

Bestv wishes, Alice

PS swimwear is coming into it as well, I'm going on holiday soon and I've promised myself that I will wear a one-piece and a bikini on the beach (that's progress!!) photo's to follow!

When I was younger I mostly thought about dressing but rarely did it. When I did it was just a skirt or a leotard and no accessories.

When I turned 50 I decided to try "it all". The first time was awful, but it got better. I knew I was on the right track when I sat down at my vanity , looked in the mirror, and saw my sister!

I started.going out first with my wife. Jeans and frilly tops at first. Skirts a little later. I would get.to wear something a little dressier when we would go out to an evening show.

I got better as the years went on and met some other t-girls. When I started going out with them I was free to use more makeup and sexier clothes. I started out a little shy but how shy can you be when your dancing in clubs in downtown Boston in a cocktail.dress?

I've started to find my own style so now I usually wear a halter dress as it seems to flatter my shape the best. I think the thing that has evolved the most is my face. Both in my makeup and my familiarity. Just looking at my pictures I can see how I smile, how I hold my head, and just my expressiveness.

I now run a t-girl group twice a month. That gets me out to the club dressed up during q regular month and then I try to get out shopping during the day too. I love.getting really dressed up and doing karaoke and dancing. I would have to say that I enjoy the days the most.when I can just go out shopping or dining with my wife or daughter. I love when the waitress says hello ladies!