Hello There,
Something I have always enjoyed and been fascinated by are Vintage photos and stories of crossdressers and transgender women. You know how much I love vintage and retro styles so to see gender non-conformists actually enjoying these styles during the time they were popular is always fun. It's also super interesting to me see how men's enjoyment of women's clothing and their desire to feel feminine transcends time, and there has always been transgender and gender fluid people living amongst us. The decade we're focusing on in todays post is the swinging sixties!
I'm starting with the sixties because of the cultural revolution that happened at the time, which brought about a lot of fun societal change including some men becoming more accepting of their true feminine selves. Speaking of men becoming their feminine selves, what better way to start my 60s spotlight off than with some pictures of actual 1960s crossdressers and drag artists!
Now that you've seen some examples of crossdressers from the 60s, I've got three different examples of crossdressing men sharing their true life feminine stories! I've chosen these stories because of how they transcend time and can feel relatable even now. These are actually going to be words taken directly from crossdressers from the 60s who published their stories and advice and in various print publications. I haven't edited the content of any of them accept for length, and these are the exact words published in the 1960s.
Janelle
I'll first start with Janelle, a young crossdresser who repeatedly wrote to magazines to share her stories. These were taken from magazines published in 1962 and 1963, this first publication details her life story:
I am known as "Janelle," or simply "Jan" by
my friends. I am 25 years old and to the best
of my recollectable knowledge, have been impersonating women since I was about nine. Why,
I don't know, but I have long ago stopped trying
to find out why, so that I may be able to enjoy
myself the more.. I can remember occasionally wearing an article of clothing belonging to
my mother and deriving great enjoyment...
When my parents were out, I would spend
many happy hours in my bedroom wearing my
mother's clothes. Even at this early age, I
was practicing with makeup and walking in high
heels. By the time I was seventeen, I was quite
adept at this and I could fashion myself into an
attractive and convincing girl.
I had left school by now and my job was
providing me with a regular weekly income. I
decided to use some of this money to outfit myself with a complete female wardrobe to my
size, which I could use at my leisure. Nobody
knew of this and I preferred to keep my activities a secret, at least for the time being.
Soon after I turned
nineteen, I moved from my home to a flat in
the Bohemian section of the city, known as
Kings Cross.
Here my life really began. I had not been
there long when I met, purely by accident, two
men who apparently had the same ideas as myself. We became quite friendly and made it a
practice to visit each other frequently. We
spent many enjoyable times together, dressed
as girls.
During my stay at Kings Cross, I met many
girls, most of whom were very unimpressed
when they discovered my secret passion. However, one of them, a very attractive and sexy
girl by the name of Denise, did not seem to
mind at all.
In fact, it came about that she would help
me by buying clothes for me and she quite often
came to my flat while I was a "girl" and was
very enjoyable company, treating me as she
would any of her female friends. She excited
me, this girl, as no other girl ever had and I
became very fond of her. She seemed to return the feeling and eventually we fell in love.
I had now acquired a job as a country representative for a major oil company and when my transfer to the country was eminent, I asked
Denise to marry me, which she, to my great
surprise, agreed to do. We have been married happily for two years
now. This is something I had never dreamed
would happen to me, but I was just lucky enough
to find a girl who was not worried by my unusual
desires. My wardrobe is now larger than ever
and although we live most of the time as man
and wife there are many occasions when we
both relax in the privacy of our home as sisters.
So that is my story. Just for the record, I
am 5' 9" tall in stocking feet (exactly 6' 0" with
high heels) and my figure is 38" 26" 37". My
greatest loves are high heeled shoes and lacey
nylon undies.
Sounds like Janelle had quite the happy ending! Getting to live with someone who is both accepting and supportive of your feminine lifestyle is an absolute dream! It's also so interesting to me to hear how Janelle started dressing when she was a child in her mom's clothes like so many of us did, including myself. I chose Janelle specifically because of how much her and her story reminded me of myself, and my goals for my life.
This next letter from Janelle discusses the problems associated with men buying women's clothes for themselves. Sixty years later this is a problem so many men and boys still struggle with, it is still awkward to buy women's clothes. Well in 1963 these were Janelle's tips on how to obtain your own women's clothing:
For several years now, I have been accustomed to wearing dresses and nylons and other
items not originally intended for men. I have
always been attracted to the idea of a male being artistic enough and handsome in order to
impersonate a girl convincingly.
Although I am not a professional at this
sort of thing, I have picked up some very useful information which you might pass on for the
benefit of other femme mimics who read your
wonderful books, with certain problems they
may have and would want to solve.
One problem facing many males who would like to try to imitate a female is where to get
clothes. For obvious reasons, very few men
are whiling to walk up to a counter in the feminine department of a store and commit themselves to buying the frilly confections on display.
Although it seems harmless enough for a
man to purchase a lace gown or some assorted
lingerie, still it is embarrassing to have saleswomen smile or make insinuating remarks.
My solution to this is to order feminine attire
by mail.
There are many mail-order houses which
send out fashion catalogues regularly and have
no objections to sending dresses and such to
customers who give only their last names and
their initials. In fact, these companies will
just as readily mail women's fashions to men
also.
Anyone can send to Sears Roebuck or to
Spiegel's of Chicago for a catalog and if you
order at least twice from it, they will put you
on their mailing list for the next issue.
Catalogs, amazon before amazon existed. It's funny that most people nowadays who try to keep their feminine purchases secret order through amazon, and sixty years ago people were doing the exact same thing with catalogues. The struggle of gender non-conformists and the solutions to hiding our identity really do transcend time. Since Janelle mentioned Spiegel's of Chicago I thought I'd show some examples of the types of women's clothing that were featured in one of the Spiegel's catalogues in the 1960s:
If the age listed in her letters is correct that would make Janelle 86 years old this year if she is still alive, which of course I certainly hope she is! I see so much of myself in her, from her story of how she started dressing to her written advice on how to obtain women's clothing. Hopefully in 60 years someone will look back as fondly about me as their inspiration!
Tony Winters
For our next 1960s adventure, I have a makeup tutorial done by female-impersonator Tony Winters. Make-up tutorials are all the rage nowadays on social media cites like Tik Tok, YouTube, and Instagram, but even back in the 60s there was demand for them. What I found fascinating about this tutorial was that the process of makeup application done by Ms. Winters is almost the exact same way I put on my makeup! While fashion trends have certainly changed over the decades, makeup seems to have stayed more or less the same!
"In a Quandary"
My final story from the 60s is a fun question written into Advice Column "Dear Abby" in 1968. The anonymous writer who simply named themselves "In A Quandary" asked about his obsession wearing, enjoying and underdressing women's undergarments:
DEAR ABBY: My problem may sound silly to you, but it is
very serious to me. For some years now, although I am a
male, single, and not considered effeminate, I have been wearing nylon panties under my outer male attire.
I like to sleep in baby doll pajamas and have a nice supply
of ladies' lingerie, negligees, panties, hosiery, bras - the works,
which I wear when I am alone. There is nothing "wrong" with
me, but I like the feeling of these things next to me.
My problem is keeping a good supply of these items. No
matter how carefully I launder them, they do not last forever,
and I must keep shopping for them. Such articles are sold only
in the ladies' departments, and they all have women salespeople. When I ask for pink panties (pink is my favorite color) in
size 8 (I am rather hefty) I say they are for my "wife" but
then my face gets as pink as the panties.
· I have tried mail-order houses, but they are unsatisfactory
as I like to see the merchandise before buying it. I don't care
to divulge my secret to anyone, so I must do my own shopping,
so I would appreciate any solutions you have to offer, as I do
not like the embarrassment.
Seeing as there wasn't really a single answerable question that was asked Abby had a very blunt answer for "In A Quandary":
Since you have already thought of all the alternatives and have rejected them, I can only infer that you
aren't really seeking a solution to your problem-you just like
to talk about it.
Pretty harsh answer from Abby if you ask me! I probably would have said something nice like: since this is clearly a part of your life you like to discuss, have you sought out others with common interests or written to magazines that specialize in men who wear women's clothing? See easy enough without hurting the man's feelings. Well to my friend "In A Quandary" I also enjoy wearing nylon panties, baby doll pajamas, ladies' lingerie, negligees, panties, hosiery, and bras! You are absolutely right in saying there is nothing "wrong" with you. Since we share a love for all of the things listed I thought I'd feature some more vintage pics of lingerie catalogues from the 1960s!
Finally in dedication to "In A Quandary" I threw on my most vintage inspired lingerie, because like I said I too "
like the feeling of these things next to me"! (Just ignore my bad sun burns please LOL)
Hope you enjoyed that blast from the past! The 1960s were a fun decade for many reasons, but I really enjoyed learning all about the different transgender, genderfluid, and crossdressing individuals from the decade. I also hope you found the three examples I chose to be insightful or interesting. I'm definitely planning on coming back for the next few decades, I'll just need a little while to do some research, and compile images. But anyway get ready for the sensational 70s coming soon!
-Carly
When deciding what makeup to buy I watched several videos on YouTube about basic makeup for crossdressers. After my research I made my list and ordered some items online and bought some in stores. Since I was getting all dolled up I also decided to also order my first wig. There was such a massive selection online I felt almost as overwhelmed as when choosing my makeup. I decided to go with something simple, not too expensive, and that was close to my actual hair color. The exact wig I bought is pictured to the right, it worked and looked ok for a little while. Honestly though I found myself not loving how the bangs were cut so I have since moved on to a new wig. Once I had wig and makeup in hand I was ready for my great undertaking!
