How old were you . . . . ?

General discussion of skirt and kilt-based fashion for men, and stuff that goes with skirts and kilts.

How old were you . . . . ?

Postby Happy-N-Skirts » Fri Nov 08, 2019 3:59 am

How old were you when you first discovered how much you liked to try on or wear skirts? Were you alone or did someone else suggest it? Was it your own decision? How long did it take to wear skirts outside your house?
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Re: How old were you . . . . ?

Postby oldsalt1 » Fri Nov 08, 2019 6:45 am

Put on my first skirt at 70 took about 6 months before first trip out

Now I am 74 wear skirts 50 % of the time and dresses 20%
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Re: How old were you . . . . ?

Postby Jim » Fri Nov 08, 2019 12:11 pm

Probably in my mid-50s. I was dealing with a skin irritation and I was upset at sexual discrimination in clothing when my wife was condemned for working outside bare-chested. Wearing skirts addressed both issues.
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Re: How old were you . . . . ?

Postby Sinned » Fri Nov 08, 2019 2:46 pm

I was in my late fifties and it took me a year of trying out skirts to eventually wear one outdoors. The first skirt my wife saw me wearing was the result of a fancy dress at a new year's eve party. I can't remember if it was my suggestion or not. Safe to say that the cat was out of the bag and I found that skirts were for me.
I believe in offering every assistance short of actual help but then mainly just want to be left to be myself in all my difference and uniqueness.
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Re: How old were you . . . . ?

Postby Freedomforall » Fri Nov 08, 2019 4:22 pm

My experience is rather recent. It was two years ago to be exact. So I was 47.
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Re: How old were you . . . . ?

Postby Happy-N-Skirts » Fri Nov 08, 2019 4:45 pm

As a child we had a neighbor who liked sewing and was always making dresses, costumes, etc. for her neices and grandchildren. She contacted my mother and asked if I would be a model for a sewing project. I didn't like the idea at all but the lady was always nice to me and I liked to play with her grandson and nephews. I went over to her house and she had a nearly finished dress and she practically begged me to try it on for a fitting. I didn't realize she wanted me to try on a dress she was making. I reluctantly took off my clothes down to my underwear and she put on a dress and she made marks and put in pins and turned me around, asked me to extend my arms, stood up on a platform. The process took about 20 minutes and was much like a medical exam. She took off the dress and before I could put my clothes on she said she wasn't finished and would I wait for a few minutes for another try on. I sat down in a chair wearing my underwear and she gave me some cookies while she was sewing seams and hems, buttons, zippers, etc. We tried another fitting and she was satisfied that the dress was perfect. I was not happy about trying on a dress and kept looking out the window to see if anyone could see me from outside. After I removed the dress and put my own clothes back on she thanked me and gave me a hug and said thank you for holding still. She paid me a dollar which was a lot of money for an eight year old. During the time I was wearing the dress she asked me how I liked it. I told her I didn't like girly things. I really was secretely enjoying the feeling of the dress and her hands touching me and smiling and giving me compliments to relax me, and she smelled nice. She was careful not to tell me I was cute and thanked me for being so brave. I never told anyone about it, and the fact that I enjoyed it. My mother asked me how it was. I told her it was about like getting a haircut, which I still don't like to do. She did not tell my father about it because he would probably not approve.

I liked our neighbor and she always said hi and talked to me. Now I was trying to make myself obvious so we could do more dress fitting. I was eight years old and kind of a loner except when her neices and nephews or grandson was visiting. One day I was in our front yard and one of the girls was wearing the dress that I wore for the modeling session. I became infatuated with the girl and the dress and how good it felt on me. We had sort of a bond because I wore her dress.

The neighbor lady was named Martha and would ask me to model, especially before holidays as she was making fancy dresses. I was a "dress dummy" on a few more occasions, one was while walking home from school and she needed me right away. By that time I was more than willing. I think I was a dress model about four more times over the next two years until our family moved away. I have very warm feelings about those experiences.

I never wanted to wear girl clothes after that but did think about it from time to time. It was several years later that I had an operation and male clothing was very uncomfortable. I bought some women's underwear and two skirts to wear during recovery. Ten years later I am still shopping for, looking at ads, and wearing skirts nearly every day. My neighbors are used to me walking my dog with a skirt, my wife likes me to wear skirts and gives me advice, I like to go hiking in a skirt, or driving because there is no inseam squashing me. I enjoy pulling the skirt up to enjoy the air conditioning. My skirts are "masculine", meaning stealthy and resemble shorts. I have no desire to cross dress, etc.

That was my early experience dressing up. I hope I never "recover."
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Re: How old were you . . . . ?

Postby Fred in Skirts » Fri Nov 08, 2019 6:00 pm

Lets see now I was about 70 or 71 and received some very bad chemical burns on my bum (1) that then decided to become very badly infected and spread down between my legs.
My family doc sent me to a Dermatologist. She started me wearing skirts. This was done to help the infection heal as pants were rubbing the sores so they would not heal. And with applying salves and creams three to four times a day it made sense. I wore the skirts for a little over 9 weeks straight. I had no choice that during this time I had to wear them outside. but when she told me I could wear pants again I wore a pair to town to do some business and shopping. I lasted an hour before I went home and changed back into my skirts and have been skirted since. I was crushed by the inseam about 4 times during the hour. That was the last time I wore pants or shorts.

(1) Improperly cleaned toilet seat in the grocery store. The person who was assigned to clean just put the caustic cleaner on the seat and let it dry. So when I sat down it became wet with sweat and caused the burns. It was a very hot day.

And now you know the rest of the story!! :D
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Re: How old were you . . . . ?

Postby weeladdie18 » Fri Nov 08, 2019 8:01 pm

I cross dressed with my female cousin and went out on the street when Auntie brought her on a visit before I was 10 years old ...It was Aunties idea.
My female cousin was quite exited to run round in my shorts......I was not so sure about wearing her cissy yellow dress as I could see one of my
male playmates coming up the road....things started getting more serious after I was twenty five . I do not wear trousers by choice now I am retired
and prefer to live my own life style ......... First trip out in a caftan today ...Delightfully comfortable and no comment from my friends .

I will admit that I prefer to wear a Kilt or a Caftan as both are traditional male garments ...I did consider a Caftan was a bit odd when I first saw
one being worn fifty years ago .

It is just a matter of gaining confidence when exploring a new male fashion style.
One has to dig through all the information and fashion history
as it is generally reported that members of The Skirt Café may only have one siting in the wild of a man in a skirt per year per year .
I now feel this is just another male fashion style , so go or it ......Happy skirting.........
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Re: How old were you . . . . ?

Postby weeladdie18 » Fri Nov 08, 2019 9:12 pm

I must say that wearing a skirt instead of wearing trousers is delightfully comfortable ..
I sometimes feel there is some stigma with being a man in a female skirt .....There is a mental block when I choose to dress in an alternative style as
I may be involved in a social tasking which requires the traditional style of attire as part of the body language .

This may go back to the days when we had to wear our school uniform per the book or we were reprimanded.

In later years children's ' school uniform was abolished . Children became undisciplined.... so the uniform was re introduced .....But not to the same standard .

Perhaps some men may admit to making a special effort to look smart when wearing a skirt.
Last edited by weeladdie18 on Sat Nov 09, 2019 6:53 pm, edited 1 time in total.
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Re: How old were you . . . . ?

Postby nzfreestyler » Fri Nov 08, 2019 11:48 pm

I was 25 when I first wore a skirt out of the house. I had tried skirts on before this age - more than once or twice but had never ventured out in a skirt.

I was wearing high heels pretty much all the time by age of 25 - and in the year or two preceeding my skirt wearing I was finding it hard to coordinate pants/trousers etc with high heels - the trouser hems and styles vs the shoes and heel height etc. I have always enjoyed being in heels and prefer them to flats and it was awkward and I didn't feel the look was right.

For me skirts just made so much style sense but it was big move to wear them - and I was very apprehensive - but was also surprised as to just how easy they were to coordinate - and just how much nicer they are to wear all year round. I have never looked back and wear all styles and I only wear trousers/pants perhaps once or twice a year at the most. I cannot recall the last time I wore jeans/trousers - its that infrequent for me now.

cheers
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Re: How old were you . . . . ?

Postby beachlion » Sat Nov 09, 2019 4:00 am

In my early 40s, I was living on my own in an apartment. At a certain moment I became curious about how it felt to walk in high heels. I ordered 2" heels and I walked in them quite comfortably. Also with 3" and even 4" heels. I wore the shoes at home and at night far away in the polders. The next step was mini skirts. Later a dress followed. To fill out the dress properly I ordered a bra and filled the cups with a plastic bag with a pint of water each. As a last experiment I went to a deserted spot along one of the rivers in the dark, dressed up completely and walked along the river for some time. After that I dumped most of the female stuff one by one. I found walking in skirts or dresses comfortable but it never occurred to me that it could be a good alternative to pants or shorts. Maybe I was indoctrinated too much into male behavior and could not yet think outside that box.

Shortly after my retirement in 2005, I found a guy on the Internet who went to trade shows in the USA in a skirt suit. From the comments it seemed he was accepted by his clients and coworkers. His comments: if a girl can wear pants than a boy could wear skirts. He found it also very comfortable. I was slightly interested but it took some years before I discovered SkirtCafe and that was the spark I needed. I had no idea how to get a skirt because I had no notion of the strange US sizing. So I converted old jeans. I found a stretch of woodland with mountain bike trails and started to walk there, hill up and hill down. There I realized how comfortable skirts were in the rough terrain.

All went in secrecy because my wife is slightly narrow minded when it comes to this kind of behavior. My breakthrough came after she watched the movie Braveheart. She asked for fun how a kilt would look on me. There is only one way to find out, I ordered a UTkilt. And the rest is history.
All progress takes place outside the comfort zone - M J Bobak
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Re: How old were you . . . . ?

Postby howardfh » Sat Nov 09, 2019 6:25 pm

About 11/12 maybe 13. The girls at school wore short gym skirts and I wanted to try them on, so I "borrowed" one while no-one was looking ant a jumble sale I was helping out in, tried it on in the toilets, loved the feel and that was that. I managed to return said item and I think it sold for around 2d.

Admits - playing hockey today - 4c with a north-westerly bitter wind, thick shorts beat a thin skirt by a mile. But it's not always winter though!!
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Re: How old were you . . . . ?

Postby weeladdie18 » Sat Nov 09, 2019 7:14 pm

Talking about Gym Skirts , I found a couple in a sports store sale due to relocation.....32 In waist , hem at my knee ....A bit of extra underclothing to
build into my rigs. Brand new £ 2 each .hard to say why we are interested in these type of garments , perhaps they are a substitute for the Roman
and Greek classic style of garments . There is some agreement of the Idea of wearing summer weight skirts with other styles of Simple skirts as
Warm layering as under clothes as the autumn temperature falls ....Now down to 14 C to 17 C.....What I would expect for this time of year....
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Re: How old were you . . . . ?

Postby JeffB1959 » Sun Nov 10, 2019 10:05 am

Let's see, I had been curious about wearing skirts for quite some time, but didn't take the big plunge until 2008 when I was 49. At the time when I decided to wear one in public, I was apprehensive as hell, thinking I'd be laughed at/pointed at/ridiculed by EVERY person in sight, and that had me quite unnerved. When that didn't happen, I felt emboldened to wear skirts more and more, as I did, that changed what I wore with them, men's shirts were replaced by women's tops, followed by women's shoes with heels low and high and everything inbetween which paired well with skirts, and I haven't looked back.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: How old were you . . . . ?

Postby crfriend » Sun Nov 10, 2019 1:26 pm

I'm guessing that my notion of skirt-wearing first gained some traction sometime in the 1970s which was the last time there was any real experimentation in men's fashion and style. Sadly, that was all swept away by the rise of the neo-con and the perpetual boom/bust cycles beginning in the 1980s.

At some point in the mid 1980s I saw a guy wearing a very long skirt on the Boston metro, and that brought the dormant idea back for a bit, but I pushed it down knowing the backlash it'd cause in my family.

In the early 2000s, with most of my elders gone, the idea returned once again -- and this time I was able to actually execute on it. I constructed my first skirt -- a white mini -- from an abandoned curtain I'd found lying around in the basement when doing the laundry one time when my late ex- was away visiting pals (back when she had any) in Florida. Fortunately, she embraced my new-found curiosity and growing sense of style and was very supportive of it -- and why not! Out of that she wound up with a bit of a changed man insofar as I now actually cared about how I looked, which was not the case before.

I've been wearing skirts ever since and haven't looked back. She's been gone a few years, but I still have all my other friends -- and nobody bats an eyelash any longer. My sense of style has evolved in the meantime. I've embraced dresses, and I'll occasionally push the boundaries of hem-length depending on venue, weather, and mood. Unfortunately, we're in the season now where the last two can be quite ratty indeed, and I've relegated all my lightweight, short, and summery stuff to a closet in the hall leaving the heavy stuff in the bedroom-closet.
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