Oh, the epic fights we used to get into about my clothes in middle/high school. You see, my parents are Artistic folks. The kind that quit jobs with no plan and live on their Artistic talents because it's SO MUCH BETTER than working for The Man (and will tell EVERYONE that's why they can't do X or Y, because being Artistic doesn't pay well).
My grandparents are more middle class typical folks that believe in careers and retirement planning, and understood that I wanted to be more 'normal'. So when they took me shopping for clothes, they let me pick out things I liked - skirts, slacks, nice dresses, blouses. I never voluntarily chose jeans or shorts or t-shirts. I still don't. My favorite outfit was, in eighth grade, a black pencil skirt, a mustard yellow turtleneck, and a black scarf tied in my hair.
My parents would yell, threaten to take things away, refuse to let me go with them places, and browbeat me because I was 'too dressed up'. I was in a long tunic top and stirrup pants (this was the late 80s, y'all - it worked then) and I was 'way too dressy to go to the movies'. Heaven forbid I wanted to wear a dress.
Now, mom compliments me on how nice I look and how thin my clothes make me look. They are essentially the same clothes.