So the other day, folks in the comments were talking about leggings. I'm pretty agnostic about leggings, but the whole discussion (which centered on the fact that it can be *really* hard to look good in leggings) got me thinking about the pervasive idea that women owe it to onlookers to maintain a certain standard of decorativeness.
Now, this may seem strange from someone who writes about pretty dresses (mostly) every day, but: You Don't Have to Be Pretty. You don't owe prettiness to anyone. Not to your boyfriend/spouse/partner, not to your co-workers, especially not to random men on the street. You don't owe it to your mother, you don't owe it to your children, you don't owe it to civilization in general. Prettiness is not a rent you pay for occupying a space marked "female".
I'm not saying that you SHOULDN'T be pretty if you want to. (You don't owe UN-prettiness to feminism, in other words.) Pretty is pleasant, and fun, and satisfying, and makes people smile, often even at you. But in the hierarchy of importance, pretty stands several rungs down from happy, is way below healthy, and if done as a penance, or an obligation, can be so far away from independent that you may have to squint really hard to see it in the haze.
But what does you-don't-have-to-be-pretty mean in practical, everyday terms? It means that you don't have to apologize for wearing things that are held to be "unflattering" or "unfashionable" — especially if, in fact, they make you happy on some level deeper than just being pretty does. So what if your favorite color isn't a "good" color on you? So what if you are "too fat" (by some arbitrary measure) for a sleeveless top? If you are clean, are covered enough to avoid a citation for public indecency, and have bandaged any open wounds, you can wear any color or style you please, if it makes you happy.
I was going to make a handy prettiness decision tree, but pretty much the end of every branch was a bubble that said "tell complainers to go to hell" so it wasn't much of a tool.
Pretty, it's sad to say, can have a shelf life. It's so tied up with youth that, at some point (if you're lucky), you're going to have to graduate from pretty. Sometimes (as in the case with Diana Vreeland, above, you can go so far past pretty that you end up in stylish, or even striking (or the fashion-y term jolie laide) before you know it. But you won't get there if you think you have to follow all the signs that say "this way to Pretty." You get there by traveling the route you find most interesting. (And to hell with the naysayers who say "But that's not PRETTY"!)