There is a kind of perennial women’s magazine article (we have even run them on this site in the past — oops) that offers tips to women on “dressing your age.” They all tend to go a little something like this: in your 20s, you can pull off almost anything. They tell you to start investing in statement bags and shoes early, but not to sweat any particular look too much — teens and twentysomethings are free! Wear a Big Bird costume to work! Wear a lamé jumpsuit! You are young and invincible. But oh, the 30s. Things start to get a little more serious. You get the big promotion and/or have a child and/or achieve your first brushes with power and success. Time to put the fast-fashion leather leggings away, time to invest in real ones from Helmut Lang. Time to start thinking about installing Dr. Scholls in your high-heeled boots (but still wear them, the magazines say, heaven forbid you get over heels before 50). Then come the 40s: more cashmere, more leather goods, more luxe. Then 50s: you turn a corner. You should be wearing all designer clothes by now, say these articles, but nothing too flashy. Stick with tailored suits and demure blazers.

But in your 60s, should you make it that far, you finally get to start having fun again, with costume jewels, big fur coats, kimonos and gaudy statement flair. The same rules seem to apply for the 70s, 80s, and 90s — magazines don’t really acknowledge women over 60, turns out. They all seem to say, wait until death is right around the corner, and then start having as much fun as you did as a child.

Style has never been about obeying fashion rules, but listening to your inner compass about where your creativity should go — where you should put your focus. When these articles tell a woman what is and is not befitting of a lady her age, it is a way of both policing individual choices and creating new mass objects of desire that can be marketed and sold. As women get older, and have more disposable income, of course the industry would benefit from telling them that they need to buy more and more goods not only to look young, but even to look properly like themselves. But glamour has nothing to do with shopping and everything to do with perfectly committing to whatever look you choose, whatever makes you feel like you can walk around with the bearing of royalty even through the hallways of an office complex or a food court. If dressing in cloaks and granny heels does it for you at 18, go for it. If you are 65 and still want to wear overalls printed with yin-yangs, truly no one can stop you but yourself.

We have all seen those people walking down the street whose outfits feel out of place and trigger a pang of judgment; our brain immediately jumps to age as the culprit: he/she is wayyyy to old to be wearing that. But that is a misplaced assessment of why a particular ensemble isn't working. What we should be thinking about, when we see someone who sets off our taste alarms, is why the person looks so uncomfortable in what they have on, why they seem to be pretending to be someone they aren't. Discomfort, rather than a mismatch of age to outfit, is truly the basis for all fashion mistakes.