Sex and the Sixties Girl: Am I Dressing for Men—Or Me?

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.

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    • Anthony Mark

      this was a very moving blog to read, thank you for sharing it with us.
      I always see you on Television and in that setting you look quite stunning. I am sure that you would look even more beautiful in person no matter how you were dressed, with or without makeup
      But this was very powerful to read more about the thought process

    • Rob

      I tried to reply to this on Twitter, but 140 characters wasn’t enough room. There’s the old adage that “If you look good, you feel good” that many people live by today. Especially women, unfortunately. I typically blame society for that, as it adds to the pressure to look a certain way to fit in or be found attractive. Personally, I wish we could all learn to be comfortable in our own skin. I live in a city where everything is about materialism and it’s difficult to find anyone true or self-secure enough to date. I long for that woman that looks good because she feels good.

    • Sam W

      Another great story. I cant wait to buy the book. Thank you Anna!

    • Joe

      It’s funny how times have changed. Back in the 1950s and 60s, women and men always dressed up, especially in the workplace. Now, everyone is a lot more casual. It’s just the change in culture. I’ve gone to the airport and seen people wearing things I wouldn’t wear in the privacy of my own closet. And don’t get me started on the Dept. of Motor Vehicles. Like Seinfeld once said, “It’s a leper colony down there.”

      From the age of 6 until a few years ago, I had to wear a tie and jacket every day (I went to Catholic schools and then worked at a software company where we had a lot of contact with customers). I kind of miss it. I liked going to a workplace where everyone dressed (and acted) professionally.

    • Marc

      I feel for you bigtime on this one. I’ve never liked dressing up. Even when I’m in a suit I fell out of place, like a giant clown. It’s not fair, but life ain’t fair.

      So I learned to cheat.

      When I’m dressed up I’m never 100% the sharp-dressed individual. Sometimes I wear an inapropriate t-shirt under my French-Cut dress shirt, and while most people comment on my polished shoes they rarely notice that they are assault boots. So in a way I’m loving myself.

      You’re journey into Ms. Brown’s shadow has been enlightening.

    • Natasha

      Not long ago, I went on a few dates with a guy who made me realize that I definitely only dress up for me, and not for anyone else, even when I’m on a date.

      He would make comments like, “Do you wear contacts? Because you don’t have to wear those just for me,” or “I like your hair short, but you’d look really hot with long hair.” He made a lot of references to my level of “hotness,” which eventually just pissed me off. Why did every conversation have to be about looks? Why did he assume that I groomed myself for his benefit?

      I do enjoy dressing up, doing makeup, and every once in a while, wearing heels. I like vintage clothes and fun hairstyles. But these are all about expressing my style. Even if my attention to looks was once far more man-focused, I feel like I’ve mostly grown out of that – though in today’s culture, with the pervasive nature of advertising, it’s hard to make such a claim with anything resembling certainty.

    • Todra Payne

      Great article. I enjoyed your transparency here.

      But to answer @Rob, I don’t think dressing up and even being fashionable signals being uncomfortable in my own skin. Nor do I feel pressured to look a certain way by society. I think just as people have different personalities, hobbies and preferences in everything, there are women like me (and men like my boyfriend) who adore fashion and LOVE dressing up every chance we get. It’s part of our personality and we do it for ourselves and for each other. We even shop together each season to snatch up the latest cool pieces. We bond over shopping and there’s nothing wrong with that. I want to look stunning whenever I leave my house. Do I always succeed? Heck no, but it’s so much fun trying. I’m always baffled by people who leave their houses looking like they just finished cleaning their garage.

    • ForEsme

      I’m a little late to jump on the bandwagon that is this article, but I am so happy you wrote about this. I feel the EXACT same way – I’m definitely conscious about how I look, but I don’t put effort in because I want to appear completely natural/not trying hard.

      Sometimes, this backfires when I feel completely inadequate next to some dolled up girl. But I wonder if that’s because I am just worried about how guys will compare me with that dolled up girl, and consider her to be more attractive. But then I ask myself, do I even want to attract a guy who prefers girls with makeup? (Which is a fine preference, obviously, but as someone who doesn’t wear makeup, probably not a great combination.)

      I, too, feel like some sort of clown/child-playing-dress-up when I wear fancy clothes.

      I’m not sure where I’m going here… but again, it was so nice to read someone who had similar experiences to mine.