The 'don't owe anyone pretty' is a hill on which I am prepared to die. I'm all for wearing whatever you like and whatever you feel comfortable in. Life is much more pleasant when I don't have to give any thought to what I am wearing, don't have to tug at hems or be restricted in any way by what I am wearing.
Day by day I don't waste any time on appearances.
However, I've been putting in a bit of effort when buying clothes for years, even decades, so that I really only own things that I at least like to wear. There is nothing else in my wardrobe and I can honestly say I have something I could wear for any event or occasion. Somethings, like tops or T-shirts, I have multiples in the same colour and style.
If I am tempted to buy anything, I consider carefully whether the potential purchase really is better than everything I already own and what I could sell or donate in order to make space for it.
As a child, I was very messy so my parents, especially my mother was often disappointed by my appearance. If we were going out, She would dress me then expect me to 'sit still and not get messy'. I promised myself I would find a better way when I was in charge of my own clothes.
Goodness, that turned a bit serious, sorry about that.