Was Crossdressing more Fun in the 1960s & 70s

[Robbiegirl]

Growing up all the girls wore such frilly items and dresses to school that it was impossible not to notice and be curious about how one would look and feel wearing them !

If you had to wear a girl cousins or neighbors clothes if yours got wet you were almost certainly going to end up in a dress. Also so many initiations at fraternities and clubs involved girls getting to doll up the boys in their clothes. Something they greatly enjoyed. In my neighborhood the girls were always putting boys into their girl scout dresses or school dresses for Truth or Dare or other games. Not as much Tv back then, so lots more crazyness !

I wonder with day to day boy clothes and girl clothes being so similar if there are far fewer boys that get curious and crossdress ?

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[Stephanie47]

My interest in wearing women's clothing did not occur until puberty. I do not recall any instances at all of boys ever donning the attire of their sisters or cousins or playmates. The real big issue in the 1950's and 1960's was confusion about sexual identity. I've stated it many times cross dressing men were deemed to be homosexuals. And to be deemed a homosexual was almost the kiss of death as to how society treated homosexuals.

I love the picture you posted. The lingerie of that era was wonderful. I don't think any little boy really cared about the lingerie. As a teenager with raging hormones and lust after women I'm sure they did not fantasize about wearing those clothes. They fantasized about getting them off a woman.

Being a cross dresser is a lot deeper than just wearing the clothes of a woman.

[Alice B]

I would have no idea as I did not start until the 90's

[sometimes_miss]

I was only a kid in the sixties; for the first few years, it was just sort of a matter of getting used to wearing girl clothes. My abuser dressed me in his sister's clothes. At home, I took my elder sister's clothes from where my mom had stored them in the attic; at first, I'd return them there when I was done wearing them, but over time, learned places to hide them in my room so I could dress whenever I wanted to. As I got into high school, I was just dressing for myself, going through all the guilt, fear of being caught, and confusion because I truly didn't know what I was, and that feeling went on for a very long time. So I wouldn't exactly call it fun. More of an odd comfortable feeling when dressed up as well as I could, and a satisfied feeling when I could do my hair up like the girls, sometimes put on some make up, too. I got it right a few times, when looking in the mirror I would actually see a cute teenage girl looking back at me. I think I might actually have been able to pass back then, except for my giant size 14 feet.

[lingerieLiz]

I admit it I was wearing all those pretty things back then. I think it was more fun for the girls and guys. I do like the casual clothes today. I don't remember the girls having the figures that many do to day. We also have more girls that are over weight and wear things to hide it which just bring it out.

[babydoll2]

In my opinion, the 70s and 80s were the golden age for lingerie, with maidenform sweet nothings, girly bikini panties (but not thongs). Ultra feminine, sexy but in a more subtle way.

[Rhonda Darling]

It was certainly more difficult for a teenager/young adult to get clothes, and dressing was MUCH riskier.

[Robertacd]

Well coming of age in the 70's/80's I do have a soft spot for those styles. I was always attentive to what the women and specially girls my age actually wore. I enjoyed looking through the catalogs at all the pretty things, I basically still do that all the time online now.

The bra I am wearing right now is a vintage store brand and style that had been around since the 70's but they quit making in the 90's. I have a handful of them and immediately buy everyone I see on E-bay in my size.

[alwayshave]

While I have dressed since the 60s, as young as 4 or 5, I can say I loved the clothes and the feel of real satin. However, I was always so fearful of getting caught. I am much more at ease with it today.

[SherriePall]

As some of the others have said, the fashions were so much more fun, but the society surrounding us was definitely not!

[Robbiegirl]

In my opinion, the 70s and 80s were the golden age for lingerie, with maidenform sweet nothings, girly bikini panties (but not thongs). Ultra feminine, sexy but in a more subtle way.

Well I do agree the Maidenform - Sweet Nothings bikini panties and Bras - were the BEST - Kind of like these

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[Janice An]

The 50's and 60's and 70's just seemed more feminine to me. I like full skirts with petticoats and you don't see that much these days.

[Teresa]

Robbie,
Maybe girls also had less of a choice then as most wore dresses or skirts , jeans were coming in but mostly Levi's which were very expensive in the UK . Usually the skirts and dresses were fuller so they needed a slip or a fuller petticoat . The mini skirt tipped things on their head , the shorter hemlines meant different underwear and worse of all the advent of tights ( pantihose ) . I loved wearing my sister's full dresses with full petticoats and stockings but wasn't so happy about mini skirts/dresses .

The choice today is mixed as any hemline is OK but women do wear trousers more than skirts and dresses . I looked round the coffee shop yesterday while having coffee with my sister in law and I was the only one wearing a skirt . If you want to dress like a woman then you have to go with the flow , I'm still enjoying it .

[docrobbysherry]

I was in middle and hi school in the 50/60's. Many boys trying on women's things is a CD fantasy!

Stephanie nailed it! The girls/women looked sexy as heck! We liked the clothes on them. But, only wanted to get the females out of them!

[Beverley Sims]

For me it was fun as I had a supporting entourage of four girsl who encouraged me.

For others it was probably frought with fear and danger as the laws were very different then, let alone the lack of acceptance by the people you may meet.

[Lorna]

One's teen years are full of questioning and impression forming. Mine were in the 1950s and early 60s. I hadn't heard of crossdressing and "transvestite" was a term used only as abuse. Nevertheless, I remember as an only child being intrigued by the very different clothes worn by girls my age - and older. I constantly wondered about how girls would be feeling as they walked to school in their skirts and dresses and I was very aware of the significance of the lingerie and underwear they wore, even though it could only be seen in catalogues, shop windows and on washing lines. The curiosity was such that I had to try it but resources for doing so were very limited. Only when I was old enough to have real girlfriends and to get close to them did I begin to find out exaclty what they wore and learn about their own experiences of those clothes. Female clothes then were so much more complicated and varied than male clothes and therefore fascinating - I wanted to try them just to find out what it felt like to be dressed like them. The endless variety not only of skirts, dresses and shoes (trousers almost unknown for women then) was easily observed every day (I watched girls trying to manage big skirts held out with stiffened slips, trying to run in heels or climb the stairs on the bus in a tight skirt and wanted to try those things for myself) but less visible were the numerous types of stockings, bras, suspender belts and girdles which they were all wearing under those clothes. I spent much time wondering what it must be like to wear those things all day and every day....something I couldn't experience but could just glimpse in my own hurried, closeted dressing sessions.
I'm afraid the enthusiasm waned with later fashion styles and is now absent altogether when almost all women and girls dress only in casual things, trousers, trainers, leggings, etc. Of course, I understand that those younger than I are just as intrigued by the female clothes that surrounded them in their own adolescent years and that those males wanting to go out into the world as women want and need to follow the clothing trends appropriate to the period and the place. For me, though, there's no doubt that the 50s and 60s were very influential.

[Linda Leigh]

In the early 60's I wore my sister's clothes and so worried about getting caught.

[Jane G]

Yes the clothes were wonderfull. Though I recall my favourite outfit in the early 70s was a black sparkley cat suit. I was far more out then, quite glam rock, but without the platforms. Hated those silly shoes. Then I went through a phase where I loved light airy summer dresses. Oh sweet memories of youth.

(Of course it was not all roses)

[Judy-Somthing]

I started dressing mid 60's so of course I became fond of the styles, stiff fabric, and the foundation garments.
Hard to believe anyone could wear a girdle all day, but they do help make a sexy figure!

[Asew]

I may be too young and naive, but I think it is more fun now. Better materials that are stretchy (thank you spandex), stronger (no more runs), easier to maintain (no more dry cleaners), and cheaper than ever (my wallet says thank you). And you buy designs from all the previous decades or buy what is trendy now. The older styles may not blend as well as they did when they were more popular, but if you wanted to blend you could wear the male wardrobe anyways

PS, no more bullet bras

[susan54]

I didn't start until the 1970's and the clothes were rubbish - A line skirts in artificial fabric, very rough sheer tights, boring underwear, shoes like clogs. There were still some old fashioned shops selling ghastly clothes like brushed nylon nighties and you could even buy directoire knickers in department stores. I bought one pair and have only worn them once - no idea where they are now. The bras and girdles were made of some horrible stiff stuff that looked a bit medical. I know you can see lovely stuff in catalogues but I suspect that this is from the 50's and 60's not the 70's. It is much better now than the 70's.

[BLUE ORCHID]

Hi Robbie Girl , I started in the Mid - Late 40s and by the 60s' & 70s' It was just what I loved to do.

>>>>>>>>>>>Orchid ..00..

[Ressie]

In the early 60's I wore my sister's clothes and so worried about getting caught.

Ditto except for me it really started in the late '60s. The fear of getting caught by family members was intense. The sexual response was also intense. It was probably more exciting as a teen but it's more fun now days.

As far as the styles from that period, yes I still love them. I've been watching Alfred Hitchcock episodes on youtube and there's usually an attractive woman wearing the style of clothes some of us covet!

[CarlaWestin]

Up until the 80's, I could have been arrested or, at least detained for some of the outfits that I wear frequently out and about and barely getting acknowledged today.

[Diane Smith]

It's hard for any of us to give a meaningful answer to this question because we were, by definition, all much younger, ignorant and inexperienced then than we are today. Many of us formed our preferences about fashion in those days and I do still think there was no better or more elegant period for women's styles than the late 1950s and early 1960s (think Audrey Hepburn or Jackie Kennedy). Lingerie and shapewear were also at their peak then. But it was also a time of huge prejudices and discrimination against those who did what we do. Overarching it all is that I was a pre-teen in the '60s and just beginning to explore and partially understand what I was interested in and what motivated me to love women's clothes. From that perspective it was natural to be confused and unable to read the cultural signs around me about what was accepted or appropriate behavior. So my reaction was to be as stealthy and closeted as possible. This created a lot of stress around dressing up and made it definitely less "fun" than today, when I can now more or less go anywhere or do anything I want. But I have 50 years more experience at it now, so it's entirely possible that the difference may be within myself as much as in the larger society.

- Diane