What Would Virginia Woolf Do?

CHAPTER ONE

(FASHION)

DEATH BY EILEEN FISHER AND OTHER FASHION TRAGEDIES

IT’S FIVE P.M. ON A Tuesday back when I still had kids at home and I’m returning from Fairway supermarket in my pajamas. My tennis elbow (a repetitive stress injury sustained not from racket sports but likely from too many hand jobs) is killing me and has not been helped by heaving jumbo-sized containers of laundry detergent into a grocery cart. I text my seventeen-year-old daughter and ask her to come help me with the groceries (it’s the only way I know I can reliably reach her, except maybe by Snapchat, whatever that is). She says she’s busy but will come down in a bit, and I’m too tired to argue, so I wait. I sit in my Subaru Outback, parked in the lot behind our building, and dip into the latest tome on menopause that has arrived from Amazon. These sorts of books have comprised my reading list for the last few months, as they have for tens of thousands of other women searching for peace of mind and advice.

Twenty minutes later, after I’ve finished a chapter on the cheery subject of uterine prolapse, my beloved child shows up, looking both sexy and adorable in a denim miniskirt, skimpy tank top, and my old Yves Saint Laurent black suede thigh-high boots. At five-four and 115 pounds, with long, blond, curly hair, perfect C cups, and many piercings, she basically looks like a twenty-first-century version of Daisy Duke (and because you’re my age, you’ll get that reference). Before she can get to me, a group of random men snapping pictures of a Lamborghini in the adjacent park intercept her to ask if she’ll pose by the car for them. True story. Again: I’m in my pajamas, with a station wagon full of groceries and an aching arm. And a couple of pimples on the lower right side of my face. I don’t feel jealous, just weary.

A reasonable question to ask is, “Why is she wearing her pajamas at five p.m. on a Tuesday afternoon?” There are a few answers to that question: I was having a brutal week of what I could only hope was PMS—I hadn’t had my period in two months, my breasts were sore, and I had seemingly put on ten pounds overnight, was having headaches, and was so tired I could barely get through the day. That afternoon I had called it quits early and at two p.m. took a bath, slipped into my pj’s (which generally consist of some sort of quasi-sexy lingerie-like top and Bedhead bottoms), and crawled into bed for a nap. With my vibrator.

An hour later I remembered that we didn’t have milk, eggs, or bread—or a plan for dinner. My last child (of four) is around for only a few more months, and on the rare evenings she and my second husband and I are all going to be together at home, I still (sometimes) valiantly try to make an effort. So I threw on a sweater and headed out to the grocery store.

The other part of the answer is that pajamas are comfortable, and they are easy to wear, and sometimes I don’t give a shit anymore about what anybody else thinks—I’ll wear what I damn well please. And if I’m being honest, I generally assume no one’s really looking anyway. This is also a tendency I must have inherited from my own mother, whom I fondly recall driving me to school in her flannel nightgowns, high ruffled collar and all. Mortified at the time, I remember begging her to drop me off a block away from the building, but now I really get it. And so do the multitudes of other women my age who wear sweats and jammies in public without thinking twice.

My teenage girl, of course, is experiencing the flip side of being almost invisible: being gawked at and objectified, with an amateur photography fan club on practically every corner. She probably put on her outfit hoping to look cute, especially to her friends, and wasn’t thinking about the fact that complete strangers might have a stake in her fashion choices. While on the outside all that attention is an ego booster, on the inside, it’s also oppressive. Walking around in your pajamas in broad daylight can be an act of liberation.

This got me to thinking about fashion in midlife in general. I do have to actually get dressed most days, and it’s often hard to figure out what to wear. Every time I leave the house I feel more pressure to consider, “Can I actually pull this off?” and it’s stressful and depressing to feel this crisis of confidence. I feel like I should be well beyond these sorts of feelings at this stage of my life.

The crux of the problem is multifold: on the one hand, I don’t want to be relegated to certain “older lady” norms or to feel like my options are shrinking. That’s just adding insult to injury, for Christ’s sake, what with hot flashes and vaginal atrophy. But on the other hand, a lot of what I already own—jeans, cute dresses, tight skirts—makes me feel like I’m trying too hard. For example, at some point, I just decided that shorts looked “bad” on me. What does that even mean? Will the sight of my less-than-taut and slightly crepey legs burn somebody’s eyeballs out? What standards do I feel the need to conform to?

As I start to slide toward the older side of the aging spectrum, I suddenly worry much more about whether I look “appropriate,” but even more important, whether what I’m wearing still makes me feel like “me,” like the person I still think of myself as. The truth is that I, like probably all of us, have internalized some sort of negative value that society tells me I have over a certain age, when I’m no longer “ripe,” with perky breasts and lustrous skin and hair. That’s beyond screwy, and it translates to a sort of immobility, a feeling of being frozen when I stand in my closet and consider my options.

A 2013 consumer studies report by Goldman Sachs points out that women’s spending on clothes peaks at forty-four, then “goes into a long slump.” For some women, middle age marks a point when we honestly aren’t as concerned with fashion and style as we used to be, but it’s much more complicated than that. Not only are our bodies changing in ways that aren’t accommodated by the latest trends, but the message is loud and clear that after a certain point, we should dispense with all sorts of items, from shorter skirts to sleeveless blouses. The rules, of course, are arbitrary, but still, many of us have swallowed them. Most women’s fashion magazines publish a splashy annual “Age” issue, purportedly to celebrate women of every generation. What the substance boils down to is a decade-by-decade breakdown of what you should and should not wear in your twenties, thirties, forties, fifties, and occasionally sixties (above which age, presumably, you are truly irrelevant to the fashion industry). So, according to this logic, what if you donned, say, a leather motorcycle jacket that’s deemed cool for a twenty-nine-year-old when you are forty-one—will you spontaneously combust?

What choices are we left with exactly? Anything that’s considered more “age appropriate”—looser clothes, suits, “slacks” (ew), even yoga or exercise clothes—makes me feel so old and fading that I can’t stand it. Fashion in midlife bounces off an inherent paradox: our bodies are starting to feel unruly, like they are betraying us (chin hair, paunch, skin sag), and at the same time there are suddenly both more rules and fewer choices.

To my mind, the solution to this quandary is a combination of humor and defiance with a healthy dollop of self-awareness. As a good friend said recently, “I wear mom jeans, Crocs, bathing suits with skirts, and could give a crap what anyone thinks.” Rock on, sister. As the designer Anne Klein said, “Clothes aren’t going to change the world. The women who wear them will.”

The bright side is that this phase of life really can be a great opportunity for reinvention. Figuring out what I want to look like, and how I want to feel in what I’m wearing, is what it’s all about. It’s not an easy process. Some of us may revel in the relief of saying good-bye to tube tops and others may mourn letting go of an item that is a poignant reminder of their younger selves. But let’s face it: as long as we’re not wearing a hospital gown or a colostomy bag, it’s all good, just best done with some ownership and thought. For me personally—and this may change—that means wearing high clogs and clothes that veer toward pajamas and lingerie.

THE TYRANNY OF HEELS—AND WHY I LOVE THEM

PART OF WHAT’S SO APPEALING about clogs is that I’m less and less able to wear high heels, which makes me want to cry. I was never a Carrie Bradshaw–like stiletto wearer. Even in my ultrayouth, my feet were wide and stilettos made me feel like an unsteady giraffe. But I remember wearing four-high-inch pumps to high school (driving there in my $250 yellow VW Bug with the rusted-out floor), and my entire adult life I’ve worn towering wedges and chunky high-heeled boots—shoes that practically feel like signature items. I love everything about heels: how they enhance my legs (one of my better features), how tall I become (my real height is a solid but not impressive five foot six), and how sexy and powerful they make me feel.

However, as great as heels are, being able to walk upright on two feet is even better. It’s been a slow process, but around three years ago I started feeling ever so slightly unsafe that far off the ground. It dawned on me that I could easily twist or even break an ankle. I said good-bye to five inches forever. Maybe it was the recognition of my own mortality, starting from the feet up. Since then, I have in fact teetered a few times, and I even tripped and fell on a sidewalk once last Christmas Eve after too much to drink. More and more I find myself gripping my husband’s arm as we hurry somewhere. I do yoga, and my balance is respectable (tree position is not a problem, even with my arms straight up above my head!), but the fact is that I’m just plain getting older and my center of gravity is unfortunately shifting upward toward my waist and midriff. The writing is on the wall. I can see that in a few years I’ll be going down to three inches, then two, and then flats… This is why, clogs.

I’m not nearly alone here. We’re giving up heels either for safety or, even more commonly, because it hurts too goddamn much to wear them now. According to the Illinois Podiatric Medical Association, women are four times more likely than men to have foot problems, generally a consequence of high heels. For one thing, pregnancy hormones weaken feet, and women are at a higher risk of stress fractures in the foot than men. Also, more than half of women get bunions, and women are nine times as likely as men to have the problem, according to the American Academy of Orthopaedic Surgeons. Some doctors say the growing popularity of high heels and pointy-toed shoes, including among very young women, has helped increase the incidence of bunions. In any case, I’m sure it hasn’t been lost on you that foot surgery for women in their fifties appears to be epidemic. In the last two years, I’ve had six friends undergo operations that sound utterly barbaric. Whether it’s damage and calcification sustained from years of pinched high heels, too much running on concrete, or simply life and genetics, they have all had procedures that involved slicing and shaving bones, inserting pins, and weeks and weeks of bed rest and crutches. And you only have one foot done at a time! After a year or so of full recovery, you can look forward to going through it all over again with the other foot! This is cruel and unusual, even by most standards of beauty sacrifice. Do men have these surgeries? Rarely. Why would they? They wear comfortable, supportive flat shoes all their lives. They don’t contort themselves into death-defying contraptions to look sexy and winsome. When you think about it, the whole thing is devastatingly messed up.

Writer Mary Karr bemoaned this ugly reality in a 2016 article for The New Yorker. At age sixty, she described her once-perfect feet as gnarled, beleaguered, and bunioned. She taped up a box of high heels that might have funded an early retirement and sent them off to Goodwill. She notes Michelle Obama’s (sensible) love of kitten heels as well as Victoria Beckham’s recent announcement that even her days of high heels are over. Following in Karr’s pained footsteps, Cindi Leive, editor in chief of Glamour