Where did you first get the idea to wear a skirt?

[moonshadow]

All,

As the title says, I'm interested to know where you all first got the idea to wear a skirt. Now I'm not really looking for the kind of answers like "I've always wanted to since xxxxxxx"... No. I don't think anybody is truly born with the notion of skirt wearing. At some point somewhere in all of our past, the idea was implanted in us.

I'm working on a hypothesis on something and I'm interested in you all's feed back. Please, be honest... it's in the name of science!

As for my answer, when I try to answer the question as honestly as possible I find that it is difficult. I often point back to my years in Damascus, witnessing male A.T. hikers wearing skirts and dresses. However quite frankly the observation of male hikers wearing skirts was only a springboard for a notion of something I've wanted to do for a long time prior, just never plucked up the courage, that is, until I witnessed other men doing it.

So I dig deeper...

I was never really interested in becoming a "woman impersonating" crossdresser. Movies like Mrs. Doubtfire never really made me want to go out and be a lady, young or old. I never really was into the whole "transvestite scene" as depicted in movies like the Rocky Horror Picture Show, to which I can say I've never seen more than a few minutes of it. When I was around nine or ten years old, my step sister and I happened upon a VHS copy of it. Thinking it was your typical "horror flick" we popped it in, and after a very short time, the both of us were quite sufficiently confused as to the exact plot! I recall telling her "this is boring", and we both went outside to play.

For the longest time I believe I was actually put off by transvestites and crossdressers, based on what few times I would see a photo or short story on them. I honestly wonder how a ten year old Moon Shadow would look upon a 37 year old Moon Shadow (today's Moon)?

This is very vexing...

The more I think about it, I believe the main factors in getting me in "women's clothes" might have been a combination of two things:

1) The fact that often times men of antiquity are depicted donning some mighty cool robes, tunics, etc. Some of the images I've seen of the great wizards of the Middle Ages, along with the mighty Roman warriors, coupled with the elegance of the priestly ritual robes and caftans of religious people. The swish of the Klingon's robes as they had their grand meetings in TNG. Bad ass, and yet, very elegant all the same. Trousers on the other hand seemed so bland and boring, utilitarian and such. Trousers are what you wear when you're plugging away on an assembly line somewhere, or digging ditches. The robes are what you wore when you were in the presence of something great, like God, or high class society.

2) Feminism. Yep. As a child of the 80's and early 90's I grew up in a world where the television made me believe that since I was born with male plumbing, I was second rate. A waste of space, and that anything I can do women can do better. And for the pro-feminist folk on this board, before you call me out, remember these were my thoughts as a TEN YEAR OLD, who probably spent more time than he should watching television. So cut me some slack. I admit I was not the crowning jewel of philosophy or much less political correctness at the ripe old age of TEN! Further, I'm NOT ANTI-FEMINIST, I'm just pointing out how the programs and mass media made me feel of myself as a child.

I would watch as pop culture depicted women entering into the man's world and excelling at it, often times better than their male counterparts. They would don their "power suits" and conquer the world, and at the end of the day, or on their weekend holidays, would dress in the most elegant dresses and gowns, or frolic in the grassy fields in some of the most beautiful skirted clothing you've ever seen. Care free, and without worry...

... and yet, me as a young man were stuck in two tubes, bland and boring. It bothered me that my world was so limited simply due to the fact that my creator formed me into a male. I often wondered why? Why do I feel so rotten about myself? Why does society believe I'm not to be trusted simply because of my anatomy? Many questions of the like, not the least of which was: Why do women get to choose their wardrobe so freely but I am restricted to one side?

I wanted to wear skirts and dresses just to spite the anti-man movement I was witnessing. Couple that with reason number one, the fact that I thought they looked cool anyway, and you have a Moon Shadow that is interested in crossing the line of genderfied clothing.

But still not quite brave enough to give it a go... that is until my time at Damascus, which is a story already well documented.

Only two members of this site have actually met in the flesh, Dillon, and Fred. I'm sure both will attest that I'm not a "flamer". Despite the fact that I wear some pretty girly stuff. My mannerisms, voice, slang, dirty jokes, etc, are what you might expect from a typical southern boy...

... I just happen to wear dresses.

I think often times when trying to figure out why we do something, when asked, the correct answer is probably the first thing that blurts out of our mouths. My answer to the question of "why I wear skirts", is normally simply because "I like them". And I often get confused looks when I offer than answer.

[Grok]

I'm 61 years old. I was a little kid during the early/mid 1960s, when most females were still mostly wearing skirts/dresses. The girls at school wore clothing that was so different from mine, I couldn't help being-secretly-curious. Curious, yes, but I kept my mouth shut. Boy weren't supposed to be interested in skirts.

[crfriend]

Please, be honest... it's in the name of science!

OK, I'll rise to this bait -- and hope the hook doesn't have a nasty barb on it.

My first consideration of the matter likely came about when I was in late single-digits or the early teenage years and being curious about why it was that the girls got to wear pretty flowing garments when the boys were all in bland and boring trousers. This was really the "Forbidden Fruit" stage, and I suspect that's what drove it. Knowing full well the outcome if I openly expressed any sort of interest in the matter I suppressed it.

Fast-forward 20-odd years. By then I was fully self-supporting, and we'd entered the time where there were young women who were attempting to wear skirts gracefully but had no clue because they received no training from their mothers. I remember commenting to my father on the matter one time as w both got a bit of a chuckle out of a young woman who was very clearly fighting with her clothes, "Dammit, that's tragic. Hell, I could do better than that." The retort to that was quick and stern, "Don't even think about it." which was a remarkable show of closed-mindedness from somebody as smart as Dad was. Sometime, likely shortly after that, I encountered the sighting on the Boston underground/subway (the "T") of a bloke in a long white skirt and remained intrigued by the notion. However, at the time, I was entirely focussed on building and strengthening my career and pushed the idea back down again. That makes at least three times I relegated the thought to the deep background.

The notion came back again in the early 2000s. With my career now in full-swing, in a stable long-term relationship, and with a job that looked stable I decided to go for it, starting out by constructing a miniskirt for myself from an old curtain that I'd found lying around. I mentioned this to my partner and, predictably, she was confused somewhat with it, but ultimately came to embrace the notion as it fundamentally changed the way I dressed (in off-hours at the time) much for the better as I now took an interest in my appearance. I still recall with a sense of awe and disappointment the sensation the first time I stepped outside and got caressed by a gentle breeze -- "I've been cheated all these years!" -- and mentioned as much to her.

She later mentioned that at one point she actively wondered whether this would affect my alignment or our relationship, and went on to say, "That's the most useless 15 seconds I've wasted in my life".

She's gone now, but I'm still wearing skirts and gradually pushing the edges of the envelope. I routinely wear stuff now that her dying brain would have regarded as way too "nice" for a guy, but she's not around any longer as a blocking influence. So, when I feel like it now, it's velvets and satins and brilliant colours. I like the present.

I never really was into the whole "transvestite scene" as depicted in movies like the Rocky Horror Picture Show, to which I can say I've never seen more than a few minutes of it. When I was around nine or ten years old, my step sister and I happened upon a VHS copy of it.

The humour in that flick is decidedly adult and juvenile at the same time. Unless you were very advanced for your age you wouldn't have "gotten it" in your early years.

I honestly wonder how a ten year old Moon Shadow would look upon a 37 year old Moon Shadow (today's Moon)?

"I'm not your father, Moonshadow, I am you from the future. Consider this carefully."

As a child of the 80's and early 90's I grew up in a world where the television made me believe that since I was born with male plumbing, I was second rate. A waste of space, and that anything I can do women can do better.

This remains the mantra to today, and the "feminists" have won. Note that the movement has nothing whatsoever to do with femininity which it relegates to degenerate status, but rather has everything to do with making women more masculine. Unfortunately, what it's produced is a travesty -- an outright parody -- of masculinity, and at the same time has seriously compromised what it really means to be a man by eroding the space we used to work within. I'm all for a level playing-field where everybody competes on their merits and where woman receive the same wage as men for a job done; however, the pendulum has swung so far that men are now actively marginalised in society to the point of being little more than ATMs, sperm-donors, and future prison-inmates.

I would watch as pop culture depicted women entering into the man's world and excelling at it, often times better than their male counterparts. They would don their "power suits" and conquer the world, and at the end of the day, or on their weekend holidays, would dress in the most elegant dresses and gowns, or frolic in the grassy fields in some of the most beautiful skirted clothing you've ever seen. Care free, and without worry...

Hilariously, it never worked that way; women are more stressed out trying to balance their lives than men ever were. This is why there are so many of them in counselling and why they're becoming ever-more-ridiculous parodies of men.

Despite the fact that I wear some pretty girly stuff. My mannerisms, voice, slang, dirty jokes, etc, are what you might expect from a typical southern boy...

As I've said before, what we wear does not define us; it's what we are inside that defines us. Only from directly astern have I ever been wrongly sexed as a woman. There has been the occasional confusion as to what I'm wearing (e.g. "I like your dress!" from a friendly liquor-store clerk in 2006 in Florida in response to my white shirt/red waistcoat/red skirt rig, or the occasional, "Nice kilt!"), and, of course, the occasional "question" about what's underneath which is usually greeted with a withering glare.

My answer to the question of "why I wear skirts", is normally simply because "I like them". And I often get confused looks when I offer than answer.

That answer is as good as any, and likely more accurate than most. What's odd is that we sometimes need to justify ourselves in the eyes of others. This is what I find somewhat offensive.

[Fred in Skirts]

Only two members of this site have actually met in the flesh, Dillon, and Fred. I'm sure both will attest that I'm not a "flamer". Despite the fact that I wear some pretty girly stuff. My mannerisms, voice, slang, dirty jokes, etc, are what you might expect from a typical southern boy...

Right you are Moon, you are not a flamer for sure. And definitely not a woman.

As for me I have always had an inclination toward skirts. In my youth I was always wearing towels around the house because they were comfortable. I just did not know that at the time that I wore them because I liked them. As I grew older and was out on my own after serving a stint in Uncles Air Farce I would wear long pieces of cloth wrapped around my waist at home again because it was comfortable. When I had my bout with the chemical burns and ensuing infection and had to wear skirts all of the time that I realized I really enjoyed the freedom that they represented and the feeling that I was being comfortable was to me just perfect.

It was at this time that I had to start wearing skirts outside of the house and had a hard time getting started. SO after a few bad starts and a doctor that told me that she would not see me if I did not follow her instructions I started to wear my skirts out of the house and much to my delight I had no problems doing so, as no one was even interested in what I was wearing...

Now skirts and dresses are all I wear no matter where I am going. I still present as a male and do not even try to act or look like a female of the opposite gender.

So that's my story whats yours?????

[beachlion]

I'm not really sure when I had the first flash. I'm not the type that digs deep into the soul to find out why I'm doing things. So I have to make a sort of reconstruction.

As a kid, I wore sometimes clothes of my mother but it was to be funny for my younger sisters. Growing up I never thought of wearing something else than the male stuff. But my first notion came from a cross dresser. I was in my early 40s when I lived in a high rise in a small town in the center of the Netherlands. Now and then I went to a bar in the city center to have a beer with some colleagues. A few times I noticed a woman that seemed familiar but I had no idea how I could have met her before. But the face was familiar. Then it dawned upon me, it was a guy that lived a few floors up and I saw him in the elevator now and then. He had quite a girly face and dressed up as a woman, he was very convincing.

It made me curious. How would it feel to be dressed as a woman. So I bought a skirt and 2" heels and walked around in my apartment. It felt not bad. A few other skirts and 3" heels followed. Then I bought a dress. That felt also nice but you have to fill up the top part. So I ordered a bra. With two plastic bags filled with a pint of water each, I came close to the size and weight of real breasts. I also added stockings and 4" heels to the repertoire. It still felt nice and wearable. But I stayed indoors.

One evening, I packed a complete outfit in my bike bags and went to a deserted spot in the nearby polders. I knew a concrete slab where they had placed barracks when they were constructing a part of the highway. Isolated so ideal to walk around in full gear. For about an hour I walked the slab up and down and also ventured out on the road. But after that, I knew how it felt and little by little it went in the garbage. The only thing I kept were boots. I had no intention or drive to keep on skirting.

But there was at least a seed planted. Much later, after my retiring, I found by accident a website about a guy that went about in skirts. I think his name was Daniel or David and he was a sort of salesman. He visited fairs and was skirted quite formally. He wore also loafers with a slightly higher heel. And from the pictures, I could see that everybody acted normal and was OK with it. And I was thinking: Why not, it is just a piece of clothing.

In the Netherlands, I did not go further with the idea because I was reconnected with my now wife and had other things on my mind. Every few months I flew to the USA to visit her. When I moved to the USA, was married and was settling in into my new world, the skirts came slowly bubbling to the surface. But how do you get a skirt? I took old jeans and modified them. You can do that as an engineer. It was coarsely sewn by hand and quite short but it felt nice. I had to keep it a secret because my wife is old school Catholic. I found a nearby piece of woodland where they had made mountain bike trails. It was ideal to walk those trails in a skirt. And the rest is history.

[Grok]

I would wear long pieces of cloth wrapped around my waist at home again because it was comfortable. er.

Improvised sarongs?

[Freedomforall]

I think my interest started when I was a small child. My sisters would dress me in their night shirt. I loved the feeling of freedom. I noticed as I grew that girls always seemed to have so many different clothing options. I always envied them for this. I also grew up hearing many women including my mother talk about how bad men were. I am not sure how this contributed to my desire to wear skirts, but I feel it did. I recall several years ago a company in Germany started marketing skirts for men. The place was called Men-in-Time, if any of you recall it. I always wanted one of their skirts but never had the nerve to buy one. It wasn't until about 2 years ago that I got the courage to try and wear kilts. It helped that my wife encouraged me as this was something I never had in my previous marriage.My previous wife did everything in her power to degrade me. She called my employer and made complaints on me, as well as spreading nasty rumors when things didn't go her way. I recall once ording a nightshirt to where and being confronted by a co-worker about it because my ex had told them I was gay. I also have to say that being a member of this forum has helped a lot.

[Jim]

I think it started with a mild underwear fetish. I didn't feel good about this fetish and decided to extinguish it by satiation without reinforcement. I then rationalized it didn't matter what sex society assigned a clothing item to.

Then there was a time with a significant crotch skin irritation that felt much better without fabric next to it, and skirts are safer than nudity. Skirts are still more comfortable much of the time. Added to this was my wife feeling oppressed feeling she had to wear a shirt when it is hot out. Skirts came to have a symbolic value of equal clothing rights for men and women.

[SkirtsDad]

Some interesting stories so far.

My earliest recollection of being dressed in a skirt was when I was probably 21. My then girlfriend, encouraged by her sister, dressed me in a long floaty orange flowered skirt and put make-up on me. Even now I can hear the swishing/rustling sound it made as I moved about. I loved the attention I was given, and the fact that my girlfriend was attracted to me like that was a bit of a turn on. I don't think that we ever went down that road again and my skirt wearing would be put on hold for over 10 years.

The next memory somewhere around the mid 90s, is completely hazy except for one comment sticks in my mind from my partner at the time, and that was her saying to me “I am the woman”. Although I used to wear leggings and over the knee socks with short shorts, which she was fine with, whatever I had put on that day had been a step too far. What it does say to me, was there was some unsatisfied desire within me.

By the end of the 90s we had gone out separate ways and I was now with someone new. She was quite different. Clothing wise she always wore short skirts, usually over leggings, but she wasn't really that fashionable other than that. On top she would typically wear a not overly flattering navy blue cardigan. Her clothing choices were functional and practical, for instance, always dark colours so that the could always be washed together as you would never know if the colours had run or not. Anyway, there was something about that look, or at least the skirt, that fascinated me.

I had taken to painting my nails at weekends and when we used to go to parties I found it got me a lot of positive attention, usually from women. With this acceptance came a desire to push boundaries further, and soon I moved on to wearing my partners denim skirts (a few of which I have to this day). I then discovered that some women, including them then partner, find a man in a skirt a bit of a turn on. Of course a skirt will often look best with certain shoes.... and here was my luck … my partner and I took the same size shoe, so that gave me an easy way in to a greater variety of footwear.

A few years on and we parted ways. I met my next partner, who was from Colombia. She had left Colombia to escape the intolerant culture and she loved the freedom of the UK. She embraced my clothing choices and encouraged me to go further. For her, it was very much about letting people be what they wanted to be. It is thanks to her in part, if not the most part, that I have the confidence to wear skirts, dresses, cropped tops and whatever else I choose out on the street.

There you are moon, it is as honest as my memory allows it to be. What I get out of wearing a skirt I certainly know, but what actually drives me to wear one, I am still not sure other than what drove me to wear peppermint green trousers in the 80s is probably the same thing somewhere along the line. It is only because it is a skirt that people question it.

[Darryl]

I have vague recollections of sharing a bath with two to three of my cousins (of the female variety) and somewhere, IIRC, there are or were two photos of me in little white dresses - at least during those years in which you do about as much falling down and crawling as you do walking/staggering. My mom and her brother definitely shared some of the same hand-me-downs in the family's pre-city days. I was one of the first "city slickers" of the family and my farm memories are generally from visiting other family members who lived out in the sticks.

Once I started grade school my Dad pretty much got me into male "uniform" with trousers and a Sunday-go-to-meeting suit. And there was the curiosity about "items" that were in the laundry process and could be observed more closely when I had the freedom to wander about the house and grounds. Never caught, or never called out, anyway.

Remember the era when school girls wore tights with their short skirts? Loved that look...maybe....if I'd had the chance to acquire some..... Never know.

Air conditioning in the old house was an open window, or later an open window with a fan in it. Lounging around in unmentionables or a light bathrobe so there are one or two old photos of my wearing a guitar more or less strategically if the robe was open, more normally if the robe was closed. Which eventually saw me lounging around in the barracks when off duty strumming my guitar while wearing a Japanese tunic of sorts...about mini-skirt length or if shorter not so short you could see unmentionables even if I was sitting and I'd "graduated" from the open-bay barracks to a 2-person room.

Pretty much back in abeyance until 2015 where I'd already been wearing support hose under trousers and then with shorts (and lamenting that the shorts weren't truly short like the ones I remembered). But having been working with my Uncle and Cousin Tracy on the family tree and the Scots-Irish, and further I finally snapped.

I'd been fascinated by kilts and Prince Charlie outfits for some time, but as I got more into the 1,000's to 1,200's in the family tree I decided I had to get one and wear it. I shared that with a friend and every time I said "kilt" she looked down and to the right and muttered "skirt." Repeat four more times.

Definitely inherited Scottish stubbornness.

A week and a half later I ordered a $30 kilt (after that came in I was more confident in the sizing and ordered a $100 version). Then I was sitting in traffic and Polly's words came back to me and I said "self - time to fish or cut bait" and detoured to Lane Bryant and asked the sales lady I wanted a skirt and what size did she think I should start with? My "Basic" store credit card was soon replaced with the "Platinum" version. As I'm only trousered 2 to 2.5 days a week now. Especially appreciate my skirts when it is in the 90's and I'm working outside or just walking for exercise. Best things since sliced bread.

The story goes that the Scots kept every one of the 10 Commandments.... … and anything else they could get their hands on. Well, this old boy done got his hands on some un-bifurcated garments.

[weeladdie18]

I am not sure where the idea started but the concept gelled and became a reality. It was a secret reality in my room at home until I gained the confidence to drive to the next town after finishing work midday on a Friday and explore the town , the countryside and beaches wearing skirts.

Please allow me to explain a bit of fashion history.... My parents were both born during WW1 1914 to 1918. I was born after my father returned from WW11... 1939 to 1945. My mother lived grew up in an era in Southern England when ladies had not normally worn trousers or shorts. My father had grown up in an era when young boys still wore dresses until the age of 5, when they were breeched to wear shorts to school. My mother lived with her four sisters so there were no boys growing up in their home.

When I was a toddler young boys still wore simple dresses with their nappies but the walking infant male was dressed mainly in shorts. We all wore shorts until we were probably aged 12 and then we wore long trousers.As far as I can remember it was probably late 1950 's to early 1960 's that we started wearing boys black wescott jeans out on the farms.

The U K suffered with material shortages and rashioning right up to the mid fifties. The G.I. Brides emigarated to America, .....The ten pound Pom emigrated to Australia.....The Merchant Navy seamen brought in the Devil' s Music in the form of the American Rock and Roll music ..Bill Haley and the Commets.....Rock around The Clock. We did not have T V until we took over my Grandfather ' s "Rent A Set " in 1960. In the 1950' s the Rock and Roll Dance became popular ,with the young working men in their Teddy Boy Drape Suits and Brothel Creepers and Western Style Bootlace Ties with a D.A. Haircut.......However to the young boy the female partner ' s attire was more interesting. The Full Circle Skirt and the high heeled shoes. When the Female did a spin the hem of her skirt and net petticoats rose above her waist to give a flash of her underwear including her stockings and the straps of her suspender belt.

All this style of dress and deportment was lost in the Swinging Sixties. The magic of an era was gone.

To precis my story perhaps this is why I am happy to wear my traditional practical male Sports jacket and male shirt with the comfort and freedom of a traditional full below the
knee summer skirt.

To confuse the issue of the male style of dress ; the lassies go wild when they see me wearing my Argyle Jacket , collar and tie and a traditional 8 yard Kilt with the hem at the top of my kneecap.................weeladdie

[weeladdie18]

Moon , I would like to add this reply here . Thank you for your landscape photos of your trips .

Much of the countryside is similar to my own varied landscape in Cornwall UK. Moorland ,The Wooded River Valley. Rocky Outcrops....All on a much larger Scale.

I find your style of skirts , practical and comfortable . I will be submitting a further post relative to the way men in warmer climates wear a garment which we in U K would call a skirt. If the male had a choice and had a supplier he might have developed a popular and practical garment..like your skirt......and my alternative ... wearing the below the knee traditional summer skirt with a traditional male sports jacket

I found an old thread concerning the Roman Style Armour Skirt worn over a simple cylindrical possibly elasticated short skirt. An interesting and practical style of male dress.

Perhaps it would just be a fashion ego trip to dress in this style. .... A leather armour skirt worn over a simple cylindrical above the knee skirt perhaps this fashion is perhaps the root of the sixties leather miniskirt. ...Worn with the early nylon tights and showing the female underwear worn over the tights when the untrained female sat or stood in an indelicate position.

There is an historical suggestion that the Roman Legions did not wear brechie ? or breeches beneath their tunics until the armies moved into the Cooler Regions of Northern Europe. However many of the troups were mercinaries who may have been locals and were more warmly dressed than the original Roman Army who probably lived in a Mediteranean Climate

I found that the historical illustrations and later photos of the above "men in skirts " were a subject of interest and enquiry to the small growing boy , who was forced into wearing shorts or trousers.. ............ "because that is what boys wear "........... weeladdie

[denimini]

My partner bought me a mini skirt as a bit of a joke and insisted I try it on. Well, it felt great and I thought gee I have been missing out here.
Soon after that my partner was diagnosed with lung cancer and I never gave it another thought until one hot summer about a year or two after she had passed away. I remembered that the mini fell cool and breezy so I retrieved it and wore it around the house. It was a bit tight in the waist so ........ to cut a long story short ........ I bought another 200 and now wear them all the time, everywhere, in warm weather. So thanks to Dear Heather.

[Big and Bashful]

Not really sure what started me, I remember watching the girls at my school and how they managed their belowthe knees skirts which were either in fashion or uniform requirement at the time, straightening them on the knees brfor a friend could sit on them, catching them as they blew up at certain windy steps, the surprise when sitting down and discovering the skirt was soaked with rain. As the skirts were fairly long and A line there was a lot of loose cloth to look after.
My first ventur was trying my mothers skirts out when the house was empty, night dresses as well, I must have been in early teens I suppose.
After leaving home, eventually I found a shop that sold night-shirts and they were my first properloose clothing. Next, many years later, a kilt. In 2006, my first EBay sourced skirt arrived. Then there was Midas clothing, discovered through this site and the first skirts apart from kilts which I am happy wearing in public. I have many more skirts now but if I am going out skirted I still use the Midas cargo skirts in various lengths. Maybe my liking for skirts which modify my movements, long, tight or both, in part comes from one of my mums, ankle length, straight, no slit and no strech, not quite a hobble but certainly not one for striding out! I am still constantly on the hunt for something similar which would fit me and also have pockets. My first Midas custom skirt was slightly restricting but was lost in a boting accident when a bag swam off while I was trying not to drown.

[Fred in Skirts]

I would wear long pieces of cloth wrapped around my waist at home again because it was comfortable. er.

Improvised sarongs?

I did not know what they were called at that time. It was just comfortable to wear.