Was Crossdressing more Fun in the 1960s & 70s

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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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.

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

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.

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.

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

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.

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.

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 .

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

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!:devil:

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

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)

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!

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 :)

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.

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

>>>>>>>>>>>Orchid ..0:daydreaming:0..

Back in the early 60's I started trying woman's clothing on here and there when I could. Things I could find handy or sneak. It was fun but a bit hard to hide and a bit stressful. fast forward to 2006 when I told my wife who accepted Angie into the house the fun really started. :hugs:
Angie

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It was fun back in the 60's. I've much more fun now the my fife knows and plays along with it.:hugs:
Angie

I wasn't alive in the 60's and 70's but I will say that typically, unless a clothing store is basing their items off of trends from the past, I tend to prefer picking up vintage pieces at thrift shops.

I dunno... Girls can wear whatever they want, but lots of fashion today is very basic, skintight, and worst of all, boring! I like pretty, lacy, flowey things, and maybe a rad floral pattern here and there! I also tend to prefer to dress modestly (That goes for when I'm in guy mode as well!), and it's a lot easier to find modest clothing options when I buy older clothing.

You mean back when it was tacitly “ok” to beat the crap out of men for wearing women’s clothes? Wheeee, fun...

I didn’t go out until the middle 70S and it was much more nerve racking than today you had to be very careful where you went , and it also helped if you could fight it need be but is was worth the risk , I would do it all over again

Susie

What's the point in wondering? Assuming it was better, we couldn't go back to that time anyway.

I believe this song encapsulates my feelings on the matter.

https://m.youtube.com/watch?v=RJReBytC9So

Sitting here thinking, I prefer current styles to past decades. My zone is wearing skinny jeans and a nice blouse. I've tried dresses and skirts, but I prefer jeans especially skinny jeans.

Ahhh, the 60's & 70's, I'm sure your closet was so much more spacious then.

Patience,
The fact is if we want , there are great retro shops that sell the older styles , charity shops can have some good finds as well .

I might just ask if one of my social groups might do a sixties themed evening.

Micki,
While you are possibly right Robbie wasn't thinking along those lines . I think it was a lovely question to ask , it made me look back over that period and maybe some of the younger ones might have enjoyed our recollections .

Back in the 1960s the world was a good deal more homophobic than it is now. I knew that I loved wearing my mum's clothes, but the feeling of guilt was HUGE.


In the 1970s I was married to woman who refused to wear hosiery or heels. This provide me with the 'excuse' to do so. But I still had children to worry about, as well as a wife who could not and would not understand my position.


Also, there was not internet, and so I supposed that I was alone in my desires.


So, No I don't think crossdressing in the 1960s and 70s was fun at all! At least, that was my experience.

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Originally Posted by Robbiegirl

... Not as much Tv back then, so lots more crazyness ! ....

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From all the replies there was a lot of Tv back then, the term crossdressing (CD) did not really appear until the 60's.

The clothes were attractive, but my memories of being "transvestite" in the sixties are mostly about irresistible compulsion, followed by shame and self loathing.

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Originally Posted by 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.

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

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Originally Posted by Linda Leigh

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

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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!

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.

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

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.

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

I find that back then there was more left to the imagination. Just imagine being turned no by seeing the lace of a slip peeking out from the bottom of a skirt, I didn't even see any flesh yet and I was turned on. I remember going home from school and Masterbating the first time I seen a bra strap. Instead now there is very little imagination left, women wear almost nothing now, there's no imagination for the eye to see. Thanks for taking me back down memory lane.

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.

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.

There is still a lot of gender sexuality in teenager clothing today, and I am sure the the percentage is about the same for boys wanting to crossdress. It just isn't as big of a deal now, at least in west coast progressive areas.

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Originally Posted by Robbiegirl

Growing up all the girls wore such frilly items and dresses to school

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In the 70's? Not on a day to day basis. Maybe for school events, but not to regular classes. Girls mostly wore jeans.

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Not as much Tv back then, so lots more crazyness !

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In the 70's? There was PLENTY of TV. We'd come home from school and watch Gilligan's Island or Brady Bunch or Star Trek, or a ton of cartoons.

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Originally Posted by Micki_Finn

You mean back when it was tacitly “ok” to beat the crap out of men for wearing women’s clothes? Wheeee, fun...

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Yeah.....

I mean sure, I have some nostalgia for vintage fashion I got from watching old movies. I'm as big a fan of The Blessed Audrey Hepburn as the next classic film watcher, but those eras weren't exactly known for being accepting of ANY non-conformity.

First tried dressing in the early 60's. Probably tried my sister's clothes first but my mom's fit better. My sister was smaller than me. My mom did have a bullet bra that I liked as well as girdles and hose with a garter. When I first tried it I thought Was the only "weirdo" who ever did this. Then read about transvestites and discovered that it wasn't all that uncommon, even though I was the only one I knew of. Wonder today if I had any other classmates that also enjoyed trying on their mother's clothes.

As I matured I also discovered the sexual enjoyment of crossdressing. For me that desire is no linger a reason to dress. Not that I don't still enjoy sex, it's just no why I dress today. Still in the closet and can't decide if I want to come out. I guess you could say my wife and I are in a DADT situation. She has found some of my things, asked a very short question about why I have them. From there on, no more questions or inquiries about why I had them. When she found them and asked why I had them I would answer "I wanted to see what it was like to wear a bra, or hose, or whatever else she found." I would wait for another question but she never asked and I wasn't confident enough to start telling her more. Don't know where it will all lead as I'm getting older but don't regret trying on my mom's bras at an early age or buying my own clothes over the years.

Well the police raids on the night clubs are probably not something anyone misses.

I'm surprised that more of us don't have positive things to say about the 70's. My experience was pretty darn positive. Emboldened at least a little bit by rock groups like this https://www.youtube.com/watch?v=NM6I-pmV0RA and many others, there was a lot of crossover between boy's and girl's clothes and hair styles. I've said on here many times that I was allowed a LOT of latitude when it came to clothes and hair. The root of my parent's attitude probably had nothing to do with rock stars, but I think it lent a tiny bit of legitimacy.

BTW, the hairstyle on the singer in that video? Not uncommon. Not on me. I was rolling my hair back then, but (albeit later than 1972) I knew of several boys who straightened their hair with a big round brush and flipped it either under like that guy did or flipped it up. My uncle married a woman with a 13 year old boy who was nearly as obsessed (well, maybe not quite!) with his hair as I was. He'd stretch and straighten his hair with a blow dryer and a round brush, then flip it up in the back and spray it until it was stiff as a board.

There were lots of boys then who did not then or ever identify as crossdressers (that I know of) who wore what we'd now consider very feminine clothes, shoes, and hairstyles and nobody thought anything about it. Boys wore platform heels, tight pants with no back pockets, scoop/U-neck tops. I will say it seems funny now and was disconcerting to me then... You'd see a boy dressed in clothes that would have been equally appropriate on a girl, hair like a fashion model, but with chest hair sprouting out from his shirt and sideburns! I could never understand that, but I think that was a way of compensating.

Those were some pretty good times discovering women’s clothing, how nice it looked and wanting to try it. I loved my mom’s things and especially her girdles but tried on just about everything. Who knew I would be hooked for life and that there were actually other guys who did the same.

I think it was a lot more fun dressing back in that period. Especially the undergarments and foundations.

In the 60's it was such a fun sensation putting on a high waist panty girdle and then sliding up stockings and attaching them to the 3 garter tabs on each leg. And then the multiple hooks of the long line bra and finally letting a long, full nylon slip glide down over all the satin and nylon. And to top it off, walking and feeling the garters tug on your nylon stocking tops with each step. And the fabrics of the dresses back then were to die for and really feminine.

In the 70's I quickly adapted to pantyhose and loved wearing them with a half slip, Marcia Brady style mini dress and wedge heels. The feel of the slip swishing over the pantyhose as I walked was a great turn on.

IMO, the young gurls starting out today got left out of some really great experiences.

Technically, I started dressed in the 1970's, but I don't remember my mother's clothes being all that great. Well, maybe her pantyhose, but that was it. Her clothes got much better in the 1980's...soft polyester and silk in particular. The makeup was better, too. My sister's clothes were terrible though.

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.