It's interesting reading all the responses. This is a great thread, Summer.
As children, in the fifties, my sister and I were always very well dressed--dresses, neat shoes, matching "play sets"--think Mad Men and you have the image. Both sets of grandparents were immigrants and literally came to Canada with just the clothes on their backs, but they all had "skills", so by working very hard, they managed to make a very good life here. My maternal grandmother was a dressmaker and passed her skills on to my mother, so, as children, my sister and I always wore beautiful hand-made clothes. My mother also worked as an executive secretary during the fifties while we were children and was always the best dressed mother around in her beautiful, tailored suits.
I grew up thinking it was normal to sew all of my clothes and that everyone understood how to adjust and tailor to fit your clothing to your body. I remember being surprised having to explain what a "godet" was to my Home Ec teacher. I also remember ripping out pictures from magazines in the 60s to serve as inspiration for my own sewing projects so I could wear the Mary Quant-style dresses I loved.
My rebellion towards "looking nice".was in the latter part of the 60s when the. "hippie" craze was going full force. My mother hated jeans with a passion--to her, they were work pants. She also disliked anything worn, torn, or dirty. I wasn't a huge fan of the boho, hippie look myself, but I remember tie-dying t-shirts just to assert my right to wear what I wanted. But I suspect her views influenced more than I realized because I really have a poisoned eye for distressed denim and poorly constructed clothing. I also have to control my urge to want others to tweak an off-the-rack item to get a better fit. As my sister says: "if they don't care, why should you?" Good point, and something I need to remember.