many of yours got heritage and it would be interesting to quote the replys by the motives of boy dreams, heritage or just chance. and how was the evolution, would be an interesting study theme. i really enjoyed the story about Mychaels son and i thinkt kilt wearing will need one more generation of boys grewing up with it. children have in a way much more self conscious; they are not so manipulated by society yet.

my way was quite freaky. it started last year when i was 23.
as a political science student we can choose, from other topics, much gender studies. and as i am a modern man loving women and hating mens oppression and don t wanted just to read theories and books about it, i told to my girl-students that i wanted to go with them on saturday night to the disco club. but not only observing the girls and the behave of staring boys. i wanted to get myself disguised in a nice girl in order trying to get how it must feel in the role of a girl. reading and empathy is one thing, to live the role another. i know a girl friend working at film and i was ready to shave my arms and legs, droping a wig.
everybody told me noone would think i am girl as i am to tall, especially my quite big feet and having simply a male body shape. but it was scientific interest mixed with fun. why must science be borring...
the girls said that before i must learn how to move in skirts and stocks, at least thats the most important quest about it. so i asked my mother to make me a kilt, so that i could go in casual life for a few weeks, without looking like a transvestite in womens skirts and not absolutely weird.

so i had to get used skirts, learn how to move and i talked to my mother: my mother made me a royal stuart and blackwatch, casual, lightweight summer wear, that are until now my first tailormade ones. ;)
i wore the kilts and i felt like having nothing around my waist, just like coming from bath. from the first moment, i was liberated from trouser tyranny.
concerning my real life experiment, i never did, but i won the life experience of kilts.
i got convinced that i really must be manly girl and at least i got completely crazy on kilts and scotland that i had enough to think about.
since i wear my kilts everyday, except austrians winter when the wind is too sharp and my honey (we live together since 4 years) loved it also from the beginning.