I am so grateful that my mom was cool with most of my clothes when growning up. Then again, I tended toward preppy or jeans and fun shirt. My grandmother tried to take me clothes shopping a few times. Sometimes it worked well, but when I was about 13 we had a trial. Fortunately, my grandmother's sister was with us and for every item that I deemed "No way", Great Aunt would find something that was cool. Funny that this particular great-aunt was not known for her fashion sense or being modern.
The worse was actually my junior year. I had a date for the Sr/Jr prom (Didn't end up going, but that is another story). My folks had already planned to go to VeryBigCity over a weekend, so Mom said I could look for a dress down there. Great! Especially since all the dress shops in our little town and the nearby BigTown were all fluffy and pastels. I look like death in pastels.
While shopping, Dad - who had been very patient - found a dress he wanted me to try on. Fluffy white sweetheart with an overlay of white with little red hearts. (Think Scarlett O'Hara)
Um, no. Mom talked me into trying it on. Dad realized that while lovely, the fluffy dress was not a good idea on his already slightly fluffy daughter.
I got a beautiful red satin dress. Fire engine red.
By the time I hit kindergarten, my mom and grandmothers decided that I would have short hair. I was taken to my grandmother's hairdresser. You know the ones who "set" hair. Evelyn was her name and she decided that not only did I need my hair cut short, but every time she cut it, she would also shave the "duck tail" along the nape of my neck. My mom said that she is pretty sure that Evelyn rarely had sharp blades in the razor. I still hate when hairdressers use razors on me.
At one point (1-3 grades) I had Dorothy Hamill cut. (I swear that cut ONLY looks cute on Dorothy)
I do remember the last time my mom tried to cut my hair. I asked for layered hair. She tried, but instead of layers, she had blocks of hair. Like stairsteps. It was the one time that I threatened never to go to school over my hair.
In college I grew my hair out and mostly have had long hair as an adult. Granted it is usually in a braid, ponytail or in a mock bun.