I’ve always had an odd relationship with putting myself together. On the one hand, I’m as vain as you can get. On the other, I spend a lot of my time out in public unshowered, let alone made up, in workout shorts or sweats and a t-shirt I got for free as swag at an event. The big move I make before leaving home is usually to dab on deodorant and, on a good day, sun block.

While I have some friends who are similar, I know far more women who doll it up: eye shadow and lipstick even if they’re just going to the gym, plus heels and jewelry if they’re going anywhere else.

I never really thought about this or believed anything was notable about the way I dressed until one Saturday night when I was in my early twenties and ran into an acquaintance at a bar in San Francisco. I was wearing a button-down flannel shirt and jeans, an outfit I had thought was pretty cute when I first put it on. She was in some sort of a get-up that involved layers of fabric and glitter.

“Oh, did you just come from…somewhere?” she asked, sounding a little confused. I recall thinking that she wasn’t trying to be bitchy; she was actually flummoxed by the notion that I would choose something so casual for an evening out.

“Yes,” I told her. “My apartment.” But inside I felt suddenly ashamed. How had it taken me a good two decades to notice that other women dressed up a lot more than I did?

Of course this sort of thing is formed by how we grow up. My mom, a writer and professor, didn’t don gowns before jetting off to teach a class and we were in Northern California, where the style icon was far more likely to be Jerry—and not Nina—Garcia. Plus my mom, being a pseudo-feminist, didn’t allow me to have Barbie dolls because she thought they objectified women and held them up to unreasonable standards. At the same time, though, she put herself together and had the dressing table and stack of makeup to prove it.

I never did.

And Helen—well, let’s just say that if she’d ever had a daughter, she probably would have bought her the whole Barbie set. Many sections in Sex and the Single Girl are devoted to the importance of dressing up and putting yourself together but perhaps none summarizes her stance on the matter better than this one: “The sheer stocking, the 24-inch waist, the smoldering look have nothing to do with successful mating or procreating,” she writes, “but they say to a man, ‘I’m with it. I have tried to make myself beautiful for you. I’ve gone to a lot of trouble because I think you’re worth it and I like myself. I want you to notice me and want me.’”

Casting aside the whole 24-inch waist factor (as I’ve mentioned before, Helen has also said that anorexia helps “maintain an ideal weight”), the quote spoke to me. Suddenly showering, perfuming, dressing up and jewelring wasn’t just for sheer vanity. It was instead an expression of self-love.

So, following Helen’s recommendation that I “copycat a mentor with better taste” than me, I enlisted the help of a style maven who worked at a vintage store near where I lived and she and I slowly improved my wardrobe. Ignoring Helen’s va-va-voom-ish sartorial recommendations, I focused instead on the second half of the passage: going to the trouble of putting myself together. I added frivolous elements to my wardrobe, like expensive scarves featuring skulls and crossbones, and items I would never have considered before (a vest, anyone?) And I found, as I made more of an effort, that I did feel better about myself. I felt more a part of everyday life. As a writer, I can get away with a lot of casual wear under the auspices of “Oh, you know how writers are”—and I have. Now I wasn’t.

And yet wandering the world in skirts and blush, I also felt a little like I was wearing some sort of a mask—that, once home, I should immediately change back into my sweats and wash my face before the makeup caused blackheads (I told you I was vain).

But it’s not all about skincare and comfort. The truth is that I don’t want to be seen trying—by anyone doing anything. I seem to want people to think that all that I have and am has come naturally and effortlessly. This, as I’ve written in previous columns, has kept my life small by preventing me from trying all sorts of things I knew I wouldn’t be good at. But it’s also completely insane. I do a career, after all, that everyone knows is a struggle; even incredibly successful writers complain about what an underpaid grind it is to craft a living by the pen. I’m also open about my struggles with addiction: I wrote a book about it, speak at colleges about it, edit a website about it, and essentially will talk about it to anyone who wants to hear. I’m even, not to state the obvious, writing about how I struggle here. Clearly, I must know, I’ve been seen trying.

I guess it’s that there’s a special sort of embarrassment that comes with my making an effort in my appearance; when I do it, I think you’re going to see that I care about what you think of me and know that I took the time to try to impress you. But Helen’s key quote says the opposite—that I essentially do this for me, because I “like myself.” (Also to make men want me, but that seems secondary.) Apparently I have a hard time remembering that I can do it for me.

So I’m saying it here: if you see me in a dress and my eyelashes are curled, I look the way I do because—most days, anyway—I like myself. Who knows? You may catch me with a smoldering look or even—you never know—in a pair of sheer stockings.

Of course, if I ever get down to a 24-inch waist, we’ll both know I’ve taken things too far.