How do you become skirt wearing

[Caultron]

I thought about wearing skirts for many years, starting back in my 30's, just because they looked comfortable and provided some variety compared to wearing pants every day. And somehow I always visualized it as a solid-color pleated skirt made of Dockers-like material. But nobody was doing anything like that at the time, and I wasn't interested enough to buy off the women's rack or buck convention to that extent. I tried women's panties and pantyhose during that time but after the newness wore off they weren't interesting enough to risk the chance of detection. I tried on one of my wife's skirts or dresses a few times when everyone was away from home but didn't find my reflection in the mirror attractive.

When earrings for men became popular I adopted those, and I also changed my hairstyle to a pony tail. I still had a beard and male-pattern baldness, though, and I wore men's clothing exclusively.

Then Utilikilts came along and seemed to be just what I'd been visualizing all those years. But they were expensive and I still never saw one on the street.

Then the foreign knock-offs appeared for less than $100 and I finally tried one and liked it. And I have to say this board helped give me the courage to go out in public, which I now thoroughly enjoy. My wife was pretty negative at first but now seems resigned, and I now wear utility kilts about 90% of the time. If she didn't insist on me wearing pants when we're out together I would readily go full-time.

I've never had a desire to dress completely as a woman, nor to impersonate one. I suppose it'd be interesting to be an attractive young woman for a while, just to see if that imparts all the advantages it appears, but that's only a hypothetical mind game. I have no desire for actual transformation or surgery.

When people ask me why I'm wearing kilt, one of my stock answers is, "Residual teen-age rebellion," and that may actually hold a lot of truth.

[Sinned]

Throughout my marriage I had tried on MOH's skirts a few times when she was out and found out how comfortable they were. I have worn some female garments at odd times during my marriage or we have worn matching clothes so the skirts shouldn't have come as a complete surprise. One night a couple of years ago we were in ASDA and there was a size 16 denim type skirt on sale for £2 and I asked her if I could buy it and she said yes. I tried it on at home and wore it around the house a few times and then I bought more skirts through ebay and sale items in stores. Of course, since then she has gone very much anti-skirts but I do persevere. She did ask me recently not to wear a skirt around her but I have ignored that and she hasn't said anything since really. I get the odd sly remark but I just ignore it or try humour.

[STEVIE]

To cut a very long story short, I apparently expressed my first interest in skirts when I was three years old.
Off and on, I surreptitiously borrowed my sisters', I had 5, so plenty choice.
Opportunity, means and motive, I had all three.
What started as a childish experiment became a habit which has stayed with me come "hell or high water" for some 50 odd years.
Steve.

[Darryl]

I am unsure.

As an avid reader of science-fiction I've come across stories based on people who can switch bodies with you, who can use a machine to "shapeshift" into whatever they want (and, of course, we have Star Trek's "Founders"). And a couple other books most likely. I enjoyed them and they put interesting questions such as 'what would it feel like' and so on into my head. Over the years I have come to the conclusion it would feel normal. And, obviously, we don't have the technology or ESP to do things like that.

In 1973 while in the US Navy in equatorial climes I found and fell in love with nylon underwear. Soft, smooth, and much better at wicking away sweat than the cottony stuff I had been wearing. Back in CONUS (Continental US) I found it difficult to resupply and eventually gave up.

Since 2000 I have come to wear two articles of clothing generally considered feminine, notably support hose/tights and wear them fairly regularly in public with shorts as weather permits. Both came as recommendations and even prescriptions from a MD for health and wellness reasons.

I guess, somewhere in the last decade as I found that I still like the ladies, haven't had any desire to try impersonating one, and experiencing the feel of tights with shorts hiking through the park I began wondering...what would a skirt feel like? Found this site and have been reading posts now and then for at least two or three years if not from late 2008 and...<gulp>...finally went out and got a skirt and will likely see how it feels during a walk in the park real soon now.

As to the tights, my mom's take was "if you want to wear them, wear them." I think she'd say the same thing about a (decent) skirt. Having been raised by my mom and grandmom, and being a computer geek and bookworm, it just seems a natural progression, somehow.

I'm considering a Messenger bag, or as 'masculine' a clutch or shoulder bag as I can find. Will probably use on old fanny pack that's in good condition for a few times. I'm still bit too large to get off-the-shelf items in Sears or Dillards or wherever. As soon as I can find a cargo skirt or something that can accommodate my regular pocket load-out, it will likely become a favorite.

So, I've been wearing around the house and front porch 5 days now. And the adventure continues....

PS: Oh, and on my public outings in tights and shorts there were no police screeching up with sirens and lights, no black helicopters appeared out of nowhere, and the world didn't end.

[crfriend]

I am unsure.

How does one become [a] skirt wearing [bloke]? You put on a skirt, of course! (Where's the "Captain Obvious" smiley when I need it? )

In 1973 while in the US Navy in equatorial climes I found and fell in love with nylon underwear. Soft, smooth, and much better at wicking away sweat than the cottony stuff I had been wearing. Back in CONUS (Continental US) I found it difficult to resupply and eventually gave up.

Good stuff, and vastly better than cotton.

This is another driver in my venture into skirts -- the tactile quality of them. It's not just in the different fabrics that are available that are "off limits" to guys, either, nor the way that a skirt feels when it's in motion around you, sometimes by virtue if a local zephyr -- it's the whole shootin' match! I still very vividly recall the first time outdoors in one of my home-made minis and feeling the breeze between my legs and commenting later on to my wife that, quote, "I've been cheated all these years!" Guys have nerve endings just as well as the gals. Why do we stifle them so?

Since 2000 I have come to wear two articles of clothing generally considered feminine, notably support hose/tights and wear them fairly regularly in public with shorts as weather permits. Both came as recommendations and even prescriptions from a MD for health and wellness reasons.

That's not to be construed as "feminine" at all -- that's merely a darned good idea.

As to the tights, my mom's take was "if you want to wear them, wear them." I think she'd say the same thing about a (decent) skirt. Having been raised by my mom and grandmom, and being a computer geek and bookworm, it just seems a natural progression, somehow.

In a way I'm saddened that I my grandmother never knew of my propensity for skirts, as I suspect she might have approved. She had a way of seeing through the bullsh!t in ways that I cannot even approach.

I'm considering a Messenger bag, or as 'masculine' a clutch or shoulder bag as I can find.

Try a camera-bag. They're pretty well obsolete nowadays, but they've got lots of room, are gender-neutral, recognizable, and are padded if you've got delicate bits to carry.

PS: Oh, and on my public outings in tights and shorts there were no police screeching up with sirens and lights, no black helicopters appeared out of nowhere, and the world didn't end.

I've not had a lot of problems with the police, nor of the world ending -- it's the dratted black helicopters that plague me. Like the little one that's hovering outside my study window...

[pelmut]

My interest in skirts began through sewing.

I bought a house which depleted my savings; it needed new curtains but I could not afford to have them professionally made, so I found some secondhand ones that only needed new linings. As a child, sewing was never something I "didn't do", because my mother enjoyed sewing and would often ask me to help if the sewing machine went wrong or if she needed a second pair of hands to pin up a hem or hold fabric out of the way. I felt sure I could manage to sew on some new curtain linings - and it was encouraging to think that I didn't stand to lose too much if it all went wrong.

I got hold of a second hand sewing machine and quite enjoyed working on the curtains, especially when they turned out all right. A girlfriend then bet me that I couldn't make her a skirt, so I accepted the challenge and, with a little bit of guidance (mainly in interpreting the pattern) produced something acceptable. That started me wondering about what it felt like to wear a skirt, so I made a very simple one from some old cotton material and tried wearing it. I was hooked immediately!

Several years passed, when I made a variety of different styles and lengths to suit the seasons, but I always wore these in private and only told my closest friends. It wasn't until I started ceilidh dancing that I considered wearing a skirt in public. It was very noticeable that on warm days the male dancers suffered badly from the heat, whereas the female ones, even those in long skirts, seemed much more comfortable. A skirt was out of the question, but I thought I might get away with something resembling a kilt.

The first attempt at a kilt was a disaster, the only friend who saw it commented that it "looks like a tartan tu-tu - and for heaven's sake don't ever wear it again". The design wasn't too bad, but the material was wrong and far too 'floaty'. Once I had found the right material (a heavy acrylic fabric) I started making and wearing kilts and have done so ever since. Now I am getting old enough not to care what people think, I have started wearing some of my more 'sober' skirts in public too - and have found the people show a surprising willingness to accept them.

[Darryl]

Ok, so much for easing into things. Went out, walked about the Mall window-shopping, then fuelled the car and went to the grocer's. Then stopped on the way home for a Taco and a Burrito. Then made a few trips back and forth carrying my purchases from the car to the house.

A little more car seating practice. The Taco Bell experience was a similar sudden change from knee-high to just below mid-thigh but I had a table over me, still kept my knees together and was wearing matching black underwear. Practice.

[BobM]

Ok, so much for easing into things. Went out, walked about the Mall window-shopping, then fuelled the car and went to the grocer's. Then stopped on the way home for a Taco and a Burrito. Then made a few trips back and forth carrying my purchases from the car to the house.

A little more car seating practice. The Taco Bell experience was a similar sudden change from knee-high to just below mid-thigh but I had a table over me, still kept my knees together and was wearing matching black underwear. Practice.

And there you have it, boys and girls. Plunge right in, the water's fine.

[Jack Williams]

I'll go right along with that! As some ad slogan has it: "Just do it".

[Jack Williams]

Just reviewing all that. Mention of police: I was taking a "selfie" out on the street last year and a cop pulled up beside me. "What are you doing?" he cried. "Taking a photo of myself in my new dress." I replied. "Your camera is on the road!" he said. Yes, a leg of the tripod was indeed a foot onto the road. "I have to get the right distance." I said. He drove off.

[Jack Williams]

This may well be the photo:

What is a "selfie"? Did I take this photo?
No. A robot took it. All I did was select the best efforts after it bangs off ten at a time.
But then at the same time I have to look reasonably intelligent (not easy) while cavorting sufficient to show off the skirt/dress. So I have a lot of input nevertheless.
Great fun of course, but must look pretty depraved to bods passing by.

[Sinned]

I have a black baseball cap that I had one each produced for my team a few years ago during a jolly to America which has the letters J F D I on it. Stands for Just F***ing Do It. Our team did all the serious Incident Management and O/S developments so it was so appropriate for us. Memories, memories!

[Jack Williams]

Correct. JFDI.

[Jayce]

"HOW?" or more likely "WHY"??? My answer: One of my five sons wore shorts from 8th grade until he graduated High School. Years later, he had a Celtic Wedding, where he requested myself and his brothers wear Kilts...we... and most other male family members complied. Months after the wedding, I wore my Kilt again in the hot weather to work on my vegetable garden; I've been hooked ever since. WHY?!?!--> cooler in the hot/humid weather, more flexible in bending and squatting and less in the way when stepping over low fences/styles. SOOOooo I'm a Spring, Summer & early Fall kilt wearer. However, in the Winter...it's back to trousers. JAYCE

[BBB]

I was working on a Pacific Island and along with several colleagues got a lava lava, I was hooked as it was far more comfortable and practical than trousers, apart from pockets!. Later on I got a tube sarong in SE Asia. In 1983 I was working in Scotland and the barmaid of a local hostelry suggests that I had the arse for the kilt. 25 yrs later I got one. I had toyed with womens' skirts but they fit in the wrong places so a kilt or sarong is the answer.
I wear a kilt whenever I can, in common with many on this site my wife hates it. On the other hand when we are together on holiday she puts up with my sarongs. I wear a kilt both casually and for formal occasions. My mother loves to see me in my kilt.
It is a funny old world and I cannot wait to see us freed from restrictive dress code convention.
In practice no one notices and the few people who comment are very positive.