I recently read a book called High Heel that helped me unpack some things that I'd never fully realized about the performance of femininity. One of the main things I took from it is just how different communication through dress is for men and women.
For example, as a man, if I wear a polo shirt in a subdued color with a pair of dark-colored slacks and leather shoes, that ensemble will elicit no comment or criticism in the vast majority of the situations that I encounter. I can wear it at work, at home, to parties, to concerts, while going for a walk, even on a first date, and it will be unobjectionable. It would be inappropriate at a wedding, a funeral, or a court date, but those kinds of cases represent a tiny fraction of my life, and a dark dress suit is an equally unobjectionable uniform that checks almost all the other boxes. Slacks and a polo is the sartorial equivalent of making small talk about the weather: it's almost always safe, benign, and forgettable (you might or might not be better served by taking a bolder tack, but no one will blame you if you don't).
Reading High Heel sensitized me to the fact that there is no "universal, safe small talk" dress equivalent for women. Whatever a woman wears, she faces the likely prospect of criticism, comment, or silent judgment from someone. If a women chooses to wear high heels, that choice will elicit judgment in some common circumstances; if she instead chooses flats that too will elicit judgment in some equally common circumstances. The author's pointed exploration of Hillary Clinton's very careful shoe and dress choices for the 2016 presidential debates specifically drove home to me how difficult and situational feminine performance really is. Heels too high and too low would both send the "wrong" message, and even the shape of the heel was open to misreading. Male presidential candidates, for the most part, just have to pick whether they're going to wear a red tie or a blue tie.
It was mind-boggling to follow along with the author through the kaleidoscopic, ever-shifting tunnel of judgment that hangs on womens' everyday clothing decisions. Imagine trying to make banal small talk about the weather and having a stranger rudely tell you that you deserve to get soaked talking about the rain like that, or having your boss tell you that it was neither the time nor the place to bring up clouds, or having some number of people silently conclude that your distaste for humidity means you're really not their kind of person. I simply never grasped that "opting out" of meaningful sartorial communication (in the way that men can choose to do) is not an option available to most women (especially in professional settings). I definitely did not appreciate the sheer amount of headspace necessarily colonized by dress and its attendant issues as a result.