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

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

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

Postby jamodu » Fri Jun 01, 2018 10:50 am

My Mother died when I was very young. During Summer, I was typically left on my own in the house for 8 hours at a time. I would rummage through all the stuff around the house. I discovered my Mother's Blue Shift Dress and tried it on. I cannot explain to this day why I was attracted to wearing it whenever I could. Eventually, the house was cleared of her past existence, and I thought nothing more of my Dress wearing.

Even so, Tights appeared on the fashion scene in the late 1960's. In the 1970's, my girlfriend regularly wore dark Chocolate Brown Sheer Tights. Well into our relationship, one day when we were fooling around, I asked her to turn around and close her eyes. We were both similar in stature. I took this opportunity to put on her Tights and her matching Brown Skirt. When she opened her eyes, she was quite accepting of what I was wearing. She didn't freak out. We continued our relationship thereafter without issue. Wearing her Skirts was fantastic. What a feeling, especially in wearing her Tights too.

The relationship eventually ended. I then met my Wife to be. She is much smaller than me. When I suggested wearing her Tights she freaked out big time. We didn't speak of it again for many, many years. That is, until neurological issues regularly left my legs cold and with pins-and-needles sensations (peripheral neuropathy). I discovered that Support Tights greatly alleviated the symptoms. She accepted my reasons for wearing TIghts.

It wasn't until my Daughter left home that I decided that wearing Tights under trousers/pants was too hot. I tried on one my Wife's elasticated Skirts when she wasn't home. Memories of my teenage Skirt wearing came back to mind. I confessed to my Wife on wearing her Skirt. I complained about the double-standards on Women being able to wear trousers/pants, and got her to read Vernon Coleman's website on why Men wear Women's clothes. She accepted the arguments outlined there.

So, I bought a couple of Skirts so that I couldn't be accused of wearing hers. Then, over a space of 12 months, I underwent minor surgery on my leg to remove a Lipoma. When it reappeared, I had surgery for the second time to remove it. It became painful to wear trousers/pants during the recovery period. Due to this, I wore Skirts at home full time - and bought more, and more. My Wife became more and more accepting. She had little issue in my buying matching blouses/tops, Tights, and Shoes.

So, the next logical step was in buying Dresses. I remember wearing my Mother's Shift Dress, and subsequently bought several. They're really comfortable to wear. I now own around 20 Dresses, and a similar number of Skirts and Blouses. I've lost count on the number of Tights that I own. My Wife often complains in jest that I have a better choice of alternative clothes than she does. She admits envy on my being able to buy a wider choice of such clothes and shoes in my size than she can in hers.

Now, I wear my own Skirts and Dresses most days of the week without issue. My Wife doesn't comment at all. It has become commonplace.
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Re: Where did you first get the idea to wear a skirt?

Postby weeladdie18 » Fri Jun 01, 2018 4:02 pm

I would like to recount todays experience. ....I saw girls clothes were different

I discovered the historical pictures of the biblical times...the Jews and Arabs in their

robes ...the roman soldiers in their short tunics and possibly leather armour skirts

....there was some sort of link to the school uniform worm by the girls and this

Roman Miltary look.. ....girls in box pleated grey above the knee skirts

finally a picture of Prince Charles in his peddle car and wearing

the Kilt at the time of his mothers coronation. I had model soldiers who wore the Kilt.

Then I saw real military officers wearing the Kilt for Scottish Highland Dance training...

then a story recorded officer recruits out on the parade ground at seven o clock in the morning in a frozen Scotland dancing to the piper whilst wearing their Kilt and Plimsoles.

Photos of the Sulu and the Sarong...I was curious and explored these styles of attire..

It was a comparison of girls clothes and The unknown male fashions...never seen on the street.

Today I deceided to wear my plain long night dress under my longest fullest skirt

green with patterns , a male shirt and green Argyle Jacket.

Went out to Breakfast dressed in this manner....a male man style out fit with a long

skirt .. not a Kilt....A lady I know , who has seen me wearing the Kilt correctly out

on the street ... Said " You look very smart today."......

Are the lassies interested in man in a Kilt ?.... or are they more interested in a man in

a neat traditional Kilt jacket and male shirt ?

Have any of my friends had this fashion experience ?......At present I am pushing

the traditional Female Skirt style rather than My 35 years of Kilt wearing.

I certainly am confident with good deportment and behave like an Elderly Gentleman.

...............weeladdie
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Re: Where did you first get the idea to wear a skirt?

Postby Caultron » Fri Jun 01, 2018 8:13 pm

weeladdie18 wrote:...I certainly am confident with good deportment and behave like an Elderly Gentleman...

Then that's how others will see you, regardless of what you're wearing.
Courage, conviction, nerve, verve, dash, panache, guts, nuts, balls, gall, élan, stones, whatever. Get some and get skirted.

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

Postby skirtedbrit » Sat Jun 02, 2018 7:08 am

Nah, not an elderly gentleman, but growing old disgracefully. I didn't rebel as a teenager, but now bring it on!
In the 60s a senior academic talked of growing old gently and quietly whilst his businessman friend was going to go kicking and screaming to the grave. I am for the latter.
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Re: Where did you first get the idea to wear a skirt?

Postby hairy » Sun Jun 03, 2018 7:42 pm

I blame it all on my two older sisters dressing me up as a doll in a box aged two for a fancy dress competition. I won first prize, they also used to make me wear sisters swim bikini on the beach, but did they HAVE to make me wear top part too. No wonder I'm so mixed up.
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Re: Where did you first get the idea to wear a skirt?

Postby Mike » Mon Jun 04, 2018 12:41 pm

I thought I was a crossdresser. I loved to wear pantyhose, and figured the only way I was going to be able to wear them exposed was with a dress or a skirt. Same with heels. Well I hated crossdressing, I hated the makeup, the wig, the fake boobs, all that. Yuck. But I loved the hose, the skirts and the heels. 25 or so years ago, I started wearing hose with shorts. Everywhere. Work, play, everywhere. The world didn't end, people didn't care about what was on my legs. Then I tried skirts, very slowly. My wife didn't seem to really mind. However, I don't wear real feminine or flowery skirts, usually cargo skirts, denim, or kahki skirts. Honestly, from a distance, it probably looks more like shorts. I have some very feminine high heels, I only wear those at home, but I have plenty of shoes from the other side of the aisle that I wear publicly. I really enjoy the clothes that women wear, but I sure as heck don't want to look like / emulate a female. I just like being me.
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Re: Where did you first get the idea to wear a skirt?

Postby SkirtsDad » Mon Jun 04, 2018 6:47 pm

Mike wrote:I thought I was a crossdresser. I loved to wear pantyhose


Actually, that reminds me, although still a bit hazy.... Not long after I started to wear denim skirts out to parties I then started buying tights and hold-ups, having tried my partner's 'thin' ones (they were probably 30 or 40 denier) and enjoyed the feel of them compared with the 200+ denier leggings and footless tights I had been wearing. Suddenly this added new possibilities with a new feel and I went on to buy many different ones including some white fishnets. Although at that time I wasn't wearing them out (expect under trousers) they brought about another change. The sheer material meant that my hairs showed, which most people will probably agree is not a good look, so I started shaving my legs. It felt great, only I started to wonder what it all meant. Before this is was just clothes, but now if I wore shorts, I knew that people would see my legs were smooth. I became confused and started joining TV groups, in case I was one. Although some of the chat was ok, after persevering I realized I was a square peg in a round hole. Societal pressures are hard to escape and I feel that I was so close to going down the wrong path. Who knows where I might have ended up.
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Re: Where did you first get the idea to wear a skirt?

Postby Kilted Musician » Mon Jun 04, 2018 8:44 pm

Mike wrote:However, I don't wear real feminine or flowery skirts, usually cargo skirts, denim, or kahki skirts. Honestly, from a distance, it probably looks more like shorts...

Same here. All of my skirts are either demin, black, or khaki. Any length from mini to ankle length. Lately I've been wearing anything to from mini to ankle just about everywhere in public except for work [My boss would have a cow... ]. Looking at Moon's pics, I've grown fond of wearing ankle length, flip flops [with painted toes], and a t-shirt. A few looks but that's about it...

--Rick
You can't add more days to your Life... but you can add more Life to your days...
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Re: Where did you first get the idea to wear a skirt?

Postby weeladdie18 » Mon Jun 04, 2018 10:24 pm

I pushed the boundaries today.....I was always interested in Roman Armour Skirt ,
The Scottish Kilt and the Girls on the School bus in their box pleated skirts when We were
all School Kids.
I tried something different today. A grey box pleated skirt worn to the top of the knee cap
like a traditional Scottish Kilt. Worn with an Argyle Highland Jacket , sweater and sporran.
No comment and no problems'.
If one considers the outline....The Roman Armour Skirt, The gentleman in his Kilt,
and the School Girl in her School Skirt all have the same outline.
As far as I am concerned I just like wearing this style of clothing.

The Question for Moon is which style of clothes am I trying to wear and which style
is traditionally acceptable for a man to wear ?

Why do I wish to be different when I can traditionally wear one of the three styles ?

There was no serious buzz today as I only dress in a style which I consider to be acceptable.

I am trying to be acceptable out on the street. Generally the reflex from the lassies

is that I look smart.................weeladdie
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Re: Where did you first get the idea to wear a skirt?

Postby weeladdie18 » Tue Jun 05, 2018 9:38 am

At one time I was very confused regarding the idea of wearing girls clothes.
Back in the early seventies I started buying skirts and wearing them at home in my room.
I went through stages of building up a nice collection and then feeling guilty and burning
the whole collection.

I slowly got out on the street and was still not confident . Then I pursued a possible solution.
Hiding my identity as a TV This idea was not successful ...weeladdie
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Re: Where did you first get the idea to wear a skirt?

Postby Caultron » Tue Jun 05, 2018 5:57 pm

weeladdie18 wrote:...which style of clothes am I trying to wear and which style is traditionally acceptable for a man to wear...

I'd say the answer to both questions is, "Whatever you want."

The type of skirts for men considered traditionally acceptable varies from place to slake and from situation to situation. I suppose a kilt is the most accepted form even outside Scotland but they're still pretty unusual in day-to-day life.

Other than that, look at what well-dressed men are wearing, look what well dressed woman are wearing, translate any shorts or trousers to a similar skirt, and then go for it.

One good thing about there being no standards for skirts for me is that you get to make your own rules. So just have fun with it and let reactions be your guide.

I'd avoid the Lady Gaga outfits, though.
Courage, conviction, nerve, verve, dash, panache, guts, nuts, balls, gall, élan, stones, whatever. Get some and get skirted.

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

Postby Darryl » Wed Jun 06, 2018 10:03 pm

weeladdie18 wrote:.....I was always interested in Roman Armour Skirt ,
The Scottish Kilt and the Girls on the School bus in their box pleated skirts when We were
all School Kids.
I tried something different today. A grey box pleated skirt worn to the top of the knee cap
like a traditional Scottish Kilt. Worn with an Argyle Highland Jacket , sweater and sporran.
No comment and no problems'.
If one considers the outline....The Roman Armour Skirt, The gentleman in his Kilt,
and the School Girl in her School Skirt all have the same outline.
As far as I am concerned I just like wearing this style of clothing.
.................weeladdie


I like that, also the short skirt with black tights or leggings - from my school days. :D

As for the rest, I like this as well:
“Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming "Wow! What a Ride!”

― Hunter S. Thompson, The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967
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Re: Where did you first get the idea to wear a skirt?

Postby Caultron » Thu Jun 07, 2018 4:14 am

Darryl wrote:...As for the rest, I like this as well:
“Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming "Wow! What a Ride!”...

You only get one chance at life, so why would you not make it amazing?

And that last blaze of glory? Revel in it and never look back (except in amazement).

Rock on.
Courage, conviction, nerve, verve, dash, panache, guts, nuts, balls, gall, élan, stones, whatever. Get some and get skirted.

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

Postby foothill » Fri Jun 08, 2018 10:14 pm

Long-time crossdresser finally realized I just like the look, fit, and feel of skirts. I don't want to look female or even feminine - and probably couldn't if I tried. Which I have, but that's another story not so appropriate to this forum. I prefer skorts even though I know there is divided opinion here. They just work better for me, especially the ones with pockets.
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Re: Where did you first get the idea to wear a skirt?

Postby FranTastic444 » Sat Jun 09, 2018 12:28 am

Though I usually have a terrible memory for past events, I still clearly remember the spark that ignited my interest in wearing women's clothes all those years ago. I was stood next to my mom in our living room, backsides facing the coal fire, trying to get some warmth. For whatever reason, my mom decided that she was going to take out her dressmaking tape and measure my chest. Upon completing the measurement, she proudly proclaimed that if I were a girl I'd be in my first bra by that point. I have no idea why this struck a chord with me (maybe it just coincided with hormone changes at the onset of puberty?) – prior to this point I'd shown no interest in such matters. I dashed upstairs and took a bra, tights and a skirt out of the laundry basket (ewe) and tried them on in the bathroom. The buzz I got from this first experience of wearing women's clothing was unbelievable.

In the years that followed I dipped into the washing basket from time to time to dig out some of my mom's clothes - tights and skirts being favorites.

My interest in dressing up has ebbed and flowed over the years. I've recently started to build my own wardrobe, but this is in secret as my initial attempt to share my interest with my wife went really badly (thought for a while that she might leave me).
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