It’s not a bad question. The problems with Cosmopolitan—or rather, with the Cosmo-fication of women’s media, are manifest to the point of trite. I myself have publicly criticized women’s magazines plenty of times; for every time I’ve talked about how important they’ve been to the mainstreaming of feminism (which, in this context, I count as a good thing), I’ve cringed at a story that has passed over my desk (“How to Wash Your Face,” which was—I kid you not—soon followed by “How to Wash Your Hair,” due to its predecessor’s success among readers).

Logically, I should be fingering Helen Gurley Brown as the godmother of face-washing how-tos and insulting sex tips. I can’t do that, though, and not only because of the fondness I felt when she hand-wrote her thoughts on the premiere issue of CosmoGirl—the teen Cosmo spinoff I worked at off and on for years before it folded in 2008—and my boss giddily distributed photocopies to everyone in the office. At one point we had to start using teen male models for the Boy-o-Meter page because the readers took inordinate pleasure in tearing “real boys” apart. Of course, it turned out they took pleasure in tearing apart teen male models as well.(All I remember of her comments was that she loved Boy-o-Meter, in which readers would rate teenage boys on their looks.) Nor is it my love of the kitschy tone of Sex and the Single Girl, which I have read from cover to cover, and which always makes me feel like a vixen even if I’m just pawing through it at home in my yoga pants.

Nor—surprisingly—is my admiration of her only born from the contrarian feminist within me who wants to argue for her as a key figure in women’s history, the woman who let us all know that it was okay to like sex and that you didn’t have to be married to want it. But the issue of Helen Gurley Brown and feminism deserves solid mention here: It is easy to forget, when Cosmopolitan is now so easily mocked for its insistence upon doing the most ridiculous boudoir moves possible, that the year she took editorship of the magazine was the same year the Supreme Court struck down laws banning contraceptives for married couples. The Pill had only been available for a few years, meaning that the concept of a woman being able to have sex whenever she wished and maintain control of her reproductive system was similarly young. For Helen Gurley Brown to come out and say what plenty of young women had known for years but had been afraid to voice—“Have you got it? Can you get it? Are you sexy? Let’s see. What is a sexy woman? Very simple. She is a woman who enjoys sex.” —Sex and the Single Girlthat sex was fun, sex was delightful, sex was not to be feared, and sex could happen simply because you, a woman, desired it—was revolutionary. It was revolutionary at the time, and given the fetishization of “purity” and the fact that the only term we have for a man who sleeps around is “male slut,” it remains revolutionary today. Also, let it be known that Helen Gurley Brown identified as a feminist. Plenty of people within the women’s movement disagree with her self-appraisal; as for me, I am happy to count her among my tribe. (Factoid: Chapter 9 of Sex and the Office, “Lunchland III: A Very Special Report,” opens with an anecdote from a “beautiful young executive” named Letty Cottin, who would go on to be Letty Cottin Pogrebin, a founding editor of Ms.)

But still, no, that isn’t what made me smile that day waiting for the elevator, nor is it what brought a heaviness to my heart upon learning that the flame-haired, miniskirted, bejeweled woman I’d admired died yesterday at age 90. In fact, it wasn’t our near-introduction at all, but rather something that sprang from the first time I laid eyes on her, at the Hearst holiday party in 1999. Through the haze brought on by the candy-cane cocktails handed out by the staff of Tavern on the Green, I spotted her: She was jockeying for the shortest skirt in the room, and had topped it off with what resembled a sequined Chanel jacket (perhaps it was a sequined Chanel jacket), that flame-colored hair teased beyond belief. She was dancing and had a small entourage around her. I flew home for Christmas and breathlessly reported to my parents that I’d seen Helen Gurley Brown, and that she was wearing a miniskirt, and wasn’t that awesome?

It was awesome, but not for the reasons I believed at the time. At the time it was more about one of my first run-ins with a celebrity, akin to the time I saw Drew Barrymore at Disneyland. And I am embarrassed to admit this, but: I shared my sighting of her with the faintest hint of ridicule. She was 77 at the time, and I was at an age at which anyone over the age of 35 was more in the realm of parent than peer. To see a 77-year-old woman partying it up in a miniskirt shorter than I’d dare to wear today—it was “cute,” and a little unseemly. I understood that she had to attend the annual company party; I understood that because she was Helen Gurley Freakin’ Brown, she could probably do the electric slide and still earn our collective respect. And I also, erroneously, understood that a woman of her age to be prancing around around in a miniskirt was—well, wasn’t that better left to people who were the age of Cosmo’s readership? Wasn’t it just the tiniest bit sad?

What I did not yet understand was that the things I condescendingly perceived as “cute” were actually evidence that I was witnessing a woman who was unafraid to work it. She knew full well the penalties heaped upon women of a certain age, and she disregarded those penalties with a shrug of her possibly-Chanel-sequined shoulder. She’d published Sex and the Single Girl when she was 40; in it she wrote “If you think only the jeunes filles, the voluptuous or sleek-cat creatures are the sexy ones, you have been living in the rumble seat of an Essex roadster the past twenty-five years.” That is, not only did she write one of the country’s most influential tomes on sexuality at an age many might have considered over the hill for a woman, but if she was speaking literally of those twenty-five years, by age 15 she’d already begun to disregard the notion that one’s sexuality died out past a divinely decreed age. I have no idea whether she decided then and there that she’d never stop being, well, Helen Gurley Freakin’ Brown (or, I suppose, Helen Freakin’ Gurley; the Brown came along in 1959 with her marriage to film producer David Brown) and would wear miniskirts as short as she damn well pleased until she tired of them, or whether it simply became her way of life over time. Really, I have no idea about her private life other than what I’ve read, which is, after all, the result of a cultivated public image.

But what I can deduce is that Helen Gurley Brown had respect for the woman who tries. That may not necessarily sound like something one should respect; when it comes to self-presentation, shouldn’t authenticity trump strain, ease trump effort? Sometimes, sure. But I’m certain I’m not the only woman who would find it less difficult to walk down the street bare-faced in sweatpants than to strut along with a bright red pucker, hair done to the hilt, cleavage pushed to the chin, and clothes that announce to the world, I want to be looked at. To Sex and the Single Girl readers who objected to wearing makeup, she challenged: “Is it possible you’re a little afraid to be on—in the limelight—every single day? If your makeup were always flawless, you’d be making an open bid for attention.” Trying is the hard sell; trying is a dare. Trying is a command to the world: Look at me, for I am worth your attention. Can trying be the opposite, a sad proclamation of one’s low self-esteem, that a woman thinks all she has to offer the world is her looks? Yes, of course. But when I think of the women I know who really work it—the 51-year-old receptionist who helms her desk with a teased updo and smoky eye at 8:30 a.m., the artist who goes shopping in ball gowns to cheer herself up, the woman of a certain age who is so impeccably styled that every time I’ve been in her company I’ve witnessed a total stranger walk up to her and profess admiration—these are not women suffering from a paucity of self-esteem. These are women who are willing to try, and who are willing to tell you what they want you to see. These are the women I was willing to try to emulate when I decided I was ready to discard clothes that hid me in favor of clothes that revealed me; from them, and from Helen Gurley Brown, I learned that overcoming the fear of trying can be tantamount to freedom.

When women try—when women strive—we put ourselves on the line, more so than men because our purpose is still presumed to be you are here to be looked at. I will support the argument that we should change the paradigm; I agree that part of the answer to the scrutiny we find ourselves under, 52 years after the Pill, is to change our culture so that being looked at is no longer seen as womankind’s greatest goal. That argument also does jack squat for women living right now, as the world exists; it casts a sidelong glance at women who seize power through being seen, or who might just sometimes enjoy being looked at, or who take the traditionally passive role of being seen and transform it into an act of agency in public life and private relationships. Helen Gurley Brown intuited this; rather, she experienced it, as a woman who experienced the manifold facets of womanhood in the early 1960s. With Sex and the Single Girl, she argued that the problem wasn’t being simply looked at; it was being looked at and having no say in how you were seen.

Also sexy, per Sex and the Single Girl: clean hair, gossip, being seen without your makeup, the LBD. Unsexy: nipple hair, bitten fingernails, baggy stockings, the jitters.One can look at things like her list of what’s sexy and not—a good telephone voice and the ability to sit very still are sexy, girdles and borrowing money most definitely are not—and find a dictator of femininity, one born from that special kind of misogyny individual women occasionally serve to one another. Certainly lesser variations of her are exactly that. Yet in looking at Helen Gurley Brown’s legacy, one could find something else, something benevolent, even sisterly. For when I read her work, when I look at her life, when I recall the look of approval—no, affection—that crossed her face as she issued her silent blessing to a younger version of myself that morning at the elevator, what I find is a gift.