My Mom was a tailor (seamstress), and had a business making clothes for people and doing alterations.
I was quite tall by the time I was 11 and from about age 11 through 13 she would have me standing on a coffee table, wearing dresses and skirts while she pinned-up the hemline. She said it was the only way to get the hem straight. Sometimes she even had me wear high heels to better represent the outfits owner.
I used to revel in such activities, at least until my brother found out and told all our friends.
I still have fond memories of some of the gorgeous things I wore.
Also like others, this was during the mid to late 60's and just being able to embrace the hippie culture allowed me to express myself in more feminine ways.
It is sad to say though that I was safer on the streets (cross)dressed as a girl than as a hippie, because I lived in a neighborhood ruled by skinheads.
Oh what fond memories. I think I learned to run really fast during those years.