Times I wish I was wearing trousers

General discussion of skirt and kilt-based fashion for men, and stuff that goes with skirts and kilts.
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Damon
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Times I wish I was wearing trousers

Post by Damon »

I am 84. I got my first kilt when I was 6 and it went to a younger cousin when I was 8 because we were moving abroad. I didn't get another until I was 12. Since then I have always owned at least one kilt and I reckon worn them for a minimum of about 25 days a year, probably more often. That still adds up to 1,800 days or if they had all been consecutive then almost five years! Then, partly to bolster my own courage I started to try and recall how many times when I had been wearing a kilt and wished that I had been in trousers. It comes to four in total, only four in all those days.

1) Children's party, age 7. When it was time for the conjurer. Boys were to sit on the floor and girls on the few available chairs. Naturally I sat with the boys on the floor. The woman in charge of the party called out "You had better sit on a chair with the girls so the Conjurer doesn't have to see your knickers." Ouch! In fact I never willingly wore a kilt again to any children's party, which may have been a factor in my mother giving it away. There were exceptions. There were two other boys in our circle of acquaintances who sometimes wore kilts to a children's party. If either or both of them were going to be there our mothers coordinated over the phone and I wore mine.

2) Long train journey from London to Edinburgh, age 7. Sat in a window seat in a compartment. Another boy of about my age sat opposite. He was in short trousers. He busied himself with a coloring book most of the way. But every time I forgot and let my legs slip apart, he somehow dropped a crayon and had to get down right in front of me to pick it up, causing me to snap my knees together and feel embarrassed. My mother did not consider this reason enough to wear trousers on subsequent trips to Edinburgh.

3) Mid thirties. Visiting Portsmouth Historic ships, aboard The Warrior. There is a sort of Bridge across the deck. Most visitors go across it. I saw a woman having difficulties with her skirt in the wind as she climbed up and came down. So I let my wife, trousered, and children go up while I stayed below. Wife teased me a bit about it.

4) Mid thirties. On holiday in Scotland. Coming off a foot ferry we had to walk down a gang plank to a windy quayside. Nearly Marylin Monroe'd. Felt very embarrassed.

That's it. Four times n nearly five years.

I found this comforting. In future avoid ships, children's parties and other seven year old boys on train journeys and everything will be fine.

Damon
Faldaguy
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Re: Times I wish I was wearing trousers

Post by Faldaguy »

Damon, I hope this was facetious and said with a big smile. How bizarre that we allow such silly notions about so-called 'propriety' affect us. :oops: Given the blatant display of "private" things in store windows from Victoria's Secrets to Walmarts -- it would seem more fitting to flash them all the time! Just more confining and conforming "boxes". However, your stats should stand us in good stead -- long odds in our favor! :)
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denimini
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Re: Times I wish I was wearing trousers

Post by denimini »

That did make me smile, although unfortunately a few incidents were in your formative years.
I can add one to your summary of situations to avoid:
Don't wear a mini skirt on a tour of submarine.
My name is Anthony, please accept me for the person that I am.
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Seb
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Re: Times I wish I was wearing trousers

Post by Seb »

Damon wrote: Mon Jan 12, 2026 12:39 am In future avoid ships, children's parties and other seven year old boys on train journeys and everything will be fine.
denimini wrote: Mon Jan 12, 2026 10:22 am Don't wear a mini skirt on a tour of submarine.
:lol: Haha, made my day! Thank you both!
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Myopic Bookworm
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Re: Times I wish I was wearing trousers

Post by Myopic Bookworm »

I climbed Dun I on the island of Iona with a pilgrimage group, wearing my full weight tartan kilt. There was a gust of wind as we neared the summit, and the vicar behind me got the full benefit of my choice of underwear.
STEVIE
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Re: Times I wish I was wearing trousers

Post by STEVIE »

Damon wrote: Mon Jan 12, 2026 12:39 am I am 84. I got my first kilt when I was 6 and it went to a younger cousin when I was 8 because we were moving abroad. I didn't get another until I was 12. Since then I have always owned at least one kilt and I reckon worn them for a minimum of about 25 days a year, probably more often. That still adds up to 1,800 days or if they had all been consecutive then almost five years! Then, partly to bolster my own courage I started to try and recall how many times when I had been wearing a kilt and wished that I had been in trousers. It comes to four in total, only four in all those days.
Damon,
How many times have you worn trousers and wished that you were wearing a skirt, or even a dress?
Steve.
Damon
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Re: Times I wish I was wearing trousers

Post by Damon »

Damon,
How many times have you worn trousers and wished that you were wearing a skirt, or even a dress?
Steve.
Quite a lot probably, as my feet often get cold at the last minute. I still remember one function when I decided I didn't want to be the only guy there not wearing pants and lo and behold there were two men in kilts. One does feel a bit stupid on such an occasion. As for wearing a dress. I have only once found the courage to do that when going out to walk my dogs, and I put a jacket over the top half so the skirt bit rather looked like a kilt. One guy I met looked like he was about to say something and thought better of it at the last minute, but he didn't look like he approved. Though I don't count that as a time I wished I wasn't. It was his problem not mine.
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skirtyscot
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Re: Times I wish I was wearing trousers

Post by skirtyscot »

denimini wrote: Mon Jan 12, 2026 10:22 am Don't wear a mini skirt on a tour of submarine.


Wise counsel indeed. For my tour of a submarine (and a frigate) I chose an ankle-length skirt. No exposure, not even going up or down ladders.
Keep on skirting,

Alastair
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