These days as I work on my memoir, I’m writing about shopping for baby clothes, writing about the days when I’d throw baby Anna in the front pack and walk to a nearby children’s clothing consignment store. I loved to look at those tiny little jeans, the impossibly small shirts and sweatshirts, miniature jean jackets. As a lesbian mom I was determined to dress my daughters in gender-neutral colors and clothes, but I was also very aware that as a lesbian parent, whatever I chose to dress my kids in would be scrutinized closely. Evaluated for any hint of agenda. Judged as too masculine, too political, or god forbid, too dyke-y. Too much an extension of my own taste in clothing.

I don’t think I was prepared for the politics of clothing when I first became a mom. I certainly wasn’t aware of the enormous gulf between boys and girls clothes, even for kids who were not yet walking. Who knew toddler wear could be sexualized? And as much as I wanted to put baby Anna in those tiny blue jeans and a miniature grey sweatshirt, I resisted the urge, unwilling to open myself up to whatever criticism might come my way. Really, my dilemma only lasted until Anna could express a preference, which happened by the time she was two and demanded to wear only clothes that bore a picture from The Lion King, preferably Simba or Nala. What I wanted her to wear mattered not one whit after that. I felt fortunate if I could get her to swap the Nala dress for the Simba tshirt once a week for washing.

As I wrote about my experiences with Anna, I wondered if my mom worried what people would think about the clothes I wore as a kid? From the time I could walk, I preferred cowboy boots and buckskin jackets (thanks Grandpa) to Mary Janes and more lady like outerwear. I ached to wear my cowboy hat and checkered cowboy shirt with the pearl snaps. My mom still mostly dressed me in dresses if we left the house and until I was in the third grade I had to wear dresses to school. Granted, the year was, well, the year was sometime in the early 1970s, but feminism was taking hold by then, though the ERA would not be defeated for a few more years. I remember my parents lamenting the droves of hippies that had invaded our small town: men with long hair and women without bras. Gender lines were being crossed already, so I was not so much of a pioneer, though I had begun to stage my own little revolution.

On the days that I had Bluebirds and had to wear the insidious blue and red uniform dress, the saving grace was that I also wore a white blouse under the uniform so I could smuggle jeans to school in my lunch box and change once I got to school. I’m not sure how my mother missed the great bulge in my little tin lunchbox, the red and yellow plaid pattern straining at its edges. I loved the way I felt in my jeans, saddle shoes (not so much), and white shirt. I felt free. Boys couldn’t look up my skirt when I climbed on the monkey bars. I could properly propel myself out of the swings without worrying about skinned knees or my dress hiking up around my waist. I could play kickball and kick my hardest without worrying that my dress would fly up and reveal my little girl panties to the entire outfield.

By the time third grade rolled around, my mom and I struck a deal: I could wear pants three days a week. I was still in Bluebirds, still smuggling my jeans on Bluebirds day, so realistically, this meant only one day of dresses a week for me. This meant shopping for jeans when we went to Sears for Back-to-School shopping, and by jeans I mean shopping for boys’ clothes in the boys’ department. I would not be satisfied with some girly version of jeans; no side zippers, nor zippers up the back; no wussie zippers that might break should I slide into home plate during kickball. No. I insisted on Sears Toughskins, reinforced knees and all. And while we were in the boys’ department, why not some practical t-shirts as well in some good colors, like blue and green and red. I had no use for ruffles and pastels. I despised the scoop neck t-shirts and peter pan collars reserved for little girls. In fact, I would have been over the moon with super hero pajamas and some tightie whities as well, but Mom had to draw the line somewhere.

I saved my most vociferous arguing for the shoe department, however. I had enough of the saddle shoes—which it turns out were my mother’s own leftover fantasy from her childhood, seeing as how her mother forbid her to wear saddle shoes—what I wanted now were Waffle Stompers. Anybody remember Waffle Stompers, named for the shape of their tread, with padding around the ankles and sliver triangle eyelets? They came in dark blue, maroon, or green, and I loved them. Back in the days before Merrells and Salomons became ubiquitous, before tennis shoes/sneakers were limited to PE class, before Nike was anything but a winged Greek goddess, Waffle Stompers offered a little budding lesbian like me a sensible shoe option of which my mother was hard pressed to disapprove. For reasons that still escape me, we (and by we, I mean all children of the time) had to have dress shoes and play shoes (just as we had school clothes and play clothes). Heaven forbid the two should ever be confused. No one could wear a pair of Chuck Taylors or those insipid Keds when in school clothes. But Waffle Stompers! Waffle Stompers offered a much needed middle ground—they weren’t tennis shoes, they weren’t dress shoes. They were sturdy and leather, and they definitely did not go with dresses. I had to get me some of those. And I would not relent. I finally got my Waffle Stompers. I wore my mother down.

But what, I wonder now, did Mom make of my tomboyish ways, my insistence that I dress like a boy? With my short carrot top hair and my Toughskins and Waffle Stompers, did I give anyone pause? Did anyone pull her aside and accuse her of having an agenda? (A sales clerk did object to my father buying me a toy rifle for Christmas one year, but that’s a different blog).

It’s interesting, the politics of clothing. Still, after roughly 43 years of dressing myself and choosing my own clothes, I struggle with what to wear, with how I want to look, how I want to be seen. What I am comfortable in. Except for a brief adolescent period, from roughly the ages of 13 to 16, I’ve always felt more comfortable in decidedly unfeminine clothes. Dressing up for me has mostly meant putting on pants that aren’t jeans, a shirt/pullover combination, or a polo shirt when it’s warm enough, and something on my feet besides sneakers or hiking shoes (though recently I’ve taken to wearing my red Chuck Taylor’s as dress up shoes).

I’m such a casual dresser that even my doctor made a note of it in my chart one time: Neatly dressed. Extremely casual. At Christmas gatherings when I was in college and in my early 20s, my grandmother used to say “Pam, you look like a boy!” I always took that as a compliment, as confirmation that I was slender and fit. Now when I get called “Sir,” and I do, regularly—just a couple of weeks ago, at the LA airport, dressed in my very womanly Izod golf shorts, not to mention my more obvious and, increasingly matronly, girl parts—I just look, like “Dude? Really?” More often than not, people are appropriately mortified. But I have to wonder, what are they seeing when they look at me?

(I do realize I’m laying myself wide open here) It has to be the clothes and my short hair—I think we’ve gotten to the point that women’s clothing is so drastically different than men’s clothing that most people don’t bother to look beyond clothes to determine someone’s gender. No visible cleavage? Guy. No floral patterns or ruffles? Guy. Short hair? Guy. Not pastels? Guy (though if you’ve been to a Ralph Lauren store lately, you know that the men are wearing a lot of pink, green, and yellow these days). Last summer, I was out and about town in a tshirt, a pair of cargo shorts, and flip flops. As I was locking my bicycle to a parking meter near the Saturday Market, a woman behind me kept saying, “Sir!” “Sir!” She got mad at me for not responding and when she found out I wasn’t a Sir! she was still mad at me. I thought that was rude. And especially now that I am a woman of a certain age, I think a certain amount of invisibility is inevitable.

Early in my professional career, I put a fair effort into dressing nicely, but in my very classically tailored clothes I was often addressed as “Sir.” I shopped exclusively in the women’s sections at Nordstrom’s and Macy’s (which was then The Bon Marche) and a gal could get shirts sans floral patterns and ruffles; I wore women’s Bass Weejuns with tassels, and (tragically) a woman’s London Fog raincoat. I even occasionally wore panty hose and a dress, and sometimes tights and professional shorts, and blazers (remember that bad 80s trend?). Eventually I tailored my career choices so I wouldn’t have to ever wear panty hose again, and these days I feel dressed up if I put on a pair of worn cords and a polo shirt for work. Most days I show up in saggy-assed Levis, a gray hoodie, and my black Converse. How I dress has no bearing on how I perform at work, except that less formal makes me happier and happier workers are better workers.

So, to bring it all back around to where I started . . . maybe what’s really important about clothing is that it makes us comfortable, because when we are comfortable, we are confident. If we are confident, we are happy. If we are happy, we are better learners, players, workers, partners, lovers, parents, children, and friends. Choosing our clothes, dressing our kids—these are political acts, not just across gender, but also across class and race (different blogs altogether). Being comfortable in my own skin, let alone in what I’m wearing? Judging one another according to what we wear? I don’t have any illusions this will change, ever. I just wish I could get over it, myself.