Dressing to impress others, or dressing to conform to the needs of the societies we live in is the sort of thing that we don't admit to ourselves easily. We like to think that we dress for ourselves and our identities first, and whatever role the people around us play is always secondary. We like to think that in the free world we live in, we have the right to choose. I, too, like to think that I have always dressed according to my own likes and dislikes, but reality would suggest otherwise. I recognise that I no longer wear the types of clothes I used to wear all the time, and it's not because I no longer like my old clothes or because my style has changed dramatically. I still like my old clothes. I just choose to wear different types of things when I can do so freely.
Trends, societal norms, roles of women in society, and dress codes still have a huge impact on the way we dress in the Western world, and at the end of the day there isn't a whole lot of freedom in that. These days there is even pressure for women to systematically "find" or "develop" their personal style, as if we somehow need one to fit in. Perhaps that is why comfort-seekers are often found on the edges of any style- or fashion-related discourse. The sweatpants-wearing woman is the ultimate fashion faux-pas.