Five years ago, I stepped out of my car onto a Jerusalem street and felt an unfamiliar lightness, followed by a panicked feeling of something valuable forgotten or missing.It was the first time I’d ventured out in public without a hat in 20 years.Leaving the hat on the seat of the car was a deliberate move, an experiment, to see what it would feel like to go bareheaded. It felt good, unencumbered for the first time in decades. The sun was warm on my scalp, the breeze lifted strands of hair and laid them crisscross on my face. I indulged in old, familiar gestures: tucking my hair behind my ear, twirling a strand around my finger, shaking my head side to side.Wouldn’t it be liberating, I thought, to remove the hat once and for all? But the more I indulged this fantasy, the more heavily the past weighed on me, the louder the still, small voice became. As I headed back to the car, I saw my hat on the seat, waiting like a patient passenger.When I was single and secular, I saw the hats Orthodox women wore as a symbol of their oppression at the hands of a religious patriarchy. When I became religious and married, I adopted the very practice I had reviled. Though I spent a lifetime trying to reconcile the choice to cover my hair, I hardly had a day’s peace. The day I left my hat on the car seat signaled a change in the way I understood my place as a feminist in the Orthodox establishment and led me to the decision to discard my hats—but not to uncover my hair completely.***I grew up in a small Jewish community in Ottawa, Ontario. My family was not observant but my siblings and I attended Jewish day school and Jewish camp and celebrated Jewish holidays at the home of my more traditional grandparents. Our Jewish life was filled with contradictions: We kept kosher at home but ate treyf in restaurants, lit Shabbat candles but then watched the NHL playoffs on television. Be Jewish, but not too Jewish, the message seemed to be. As Jewish as we may have been, we were in equal measure enlightened, rational, tolerant, liberal, patriotic Canadians.When I hit my teens, the quaint, quasi-traditional lifestyle in which I had been raised seemed, all of a sudden, insufferably inauthentic and hypocritical. To make this point abundantly clear to my parents, I read The Catcher in the Rye tucked between the pages of my machzor at shul on Rosh Hashanah. On Yom Kippur, between mincha and neila, I snuck off with a friend to enjoy coffee and a cinnamon danish in a nearby café.By the time I was 18, Judaism was a relic of my past. I became a vegetarian, free spirit, activist for human rights and world peace, and, above all, a feminist. I had grown up under the banner of feminism: equal pay for work of equal value, affirmative action, take back the night. Helen Reddy’s “I Am Woman” was my anthem.What I did not realize, when I cast off all vestiges of my Jewish life, was that I had let slip away the values that had shaped me, my connection to the past and, very possibly, the essence of who I was. I would spend many subsequent years trying to retrieve a sense of meaning in my life and searching for my place in the world.That search took me from Kierkegaard to Sartre, The Brothers Karamazov to To the Lighthouse, Amnesty International to the Toronto Peace Network, Jungian dream therapy to existential psychotherapy, the jungles of Rwanda to the beaches of Elba. At the age of 26, I landed at the doorstep of Aish Hatorah. There I relearned the basic tenets of Judaism, and by and by, about the role of women—and specifically the obligation of hair covering. The rabbis explained that hair is erva, nakedness. Married women must cover their hair to reduce the risk of rousing men’s passions, they said. By covering your hair you emphasize internal over external beauty, you reserve your hair and yourself for your husband alone. They quoted Song of Songs: “Your hair is a flock of goats leaping down the slopes of Gilead.”This was Toronto in the 1980s. Feminism had not yet begun to make inroads into Orthodox Judaism. Women weren’t studying Talmud. There were no Orthodox women’s prayer groups, women’s megillah readings, women’s advocates in rabbinical courts. The rabbis said women were on a higher spiritual level than men; that’s why they were exempt from so many of the legal requirements. They didn’t need the rigors of learning and ritual to refine their souls.I didn’t buy it. I believed that hair covering perpetuated the myth of woman as temptress. It punished women for men’s inability to control their sexual impulses. No way was I subscribing to modesty edicts that obfuscated women. But at the same time, I was drawn to Orthodoxy’s emphasis on spiritual growth, ethics, and tikkun olam. I felt at home for the first time in years in the Jewish traditions of my past. Over the next few years, I took on mitzvot, carefully sidestepping those that offended my liberal, feminist sensibilities.When I began dating the Orthodox man who would become my husband, and he raised the subject of hair covering, I took up arms: “Why should I cover my hair? Standards of modesty have changed in the last hundred years. No enlightened person considers a bare head immodest.”“Take it up with the sages,” he said. “As far as I’m concerned, you can do what you like.”I would do what I liked. There was only one problem: I didn’t want to pick and choose which commandments I kept. That was the watered-down Judaism my parents practiced, the lifestyle I had rejected. The accommodations my parents had made may have worked for them as they tried to adapt their Eastern European parents’ shtetl Judaism to their Western lifestyle, but they didn’t work for me. I sought an absolute, nonnegotiable truth. The mitzvot emanated from a divine source, the norms and values were binding. Halacha was a package deal; you were in or you were out.And so for me, when I married at age 31, Judaism trumped feminism. I started wearing a hat.My mother didn’t say anything, but I knew I’d set back her cause a hundred years. My secular friends were dumbfounded; I had betrayed the sisterhood.***It wasn’t easy. I wished hair covering was something I took for granted, the way young women did who had grown up in Orthodox households and seen their mothers and aunts and grandmothers cover their hair. I wished I had felt compelled to cover my hair for love or fear of God. But I didn’t. It was, in the end, a bitter pill I had to swallow.I tried to make the best of a difficult situation. I liked the way the modesty dictates emphasized dignity and respect in relationships. Besides, it wasn’t as if my hair was my best feature. It was thin and mousy, probably better off unseen. And as a Jew, having a choice of hats beat a wimple, burqa, or Amish bonnet.A year into our marriage, my husband, son, and I moved to Israel, where people proclaim their affiliation to a religious stream by the size and style of their hair covering: Ultra-Orthodox women wear wigs or snoods. National religious women wrap their hair in scarves. More modern religious women, like myself, wear hats with different degrees of hair showing. In Canada, the hats I wore had been no more than a fashion accessory, but in Israel they defined me. I was a walking advertisement for Modern Orthodoxy, a community I was proud to represent.I started out wearing baseball caps. They were casual and cheerful and suited the young, newly married me. But when I took them off at the end of the day, my flock of goats leaping down the slopes of Gilead looked more like a bedraggled musk-ox.A couple of years later, I swapped the caps for berets, which gave me a French flair. Depending on the way I angled them, I could appear intellectual, artistic, or revolutionary. But when I took the berets off, especially the wool ones, I had hat hair again. And the berets added static, which made me look like Jimi Hendrix.Besides the endless bad hair days, there was the fashion conundrum. It was hard enough to coordinate an outfit with jewelry, a jacket, and shoes. When I added a hat to the equation, I invariably had a fashion flub.I reminded myself of a verse in Proverbs: “Grace is elusive and beauty is vanity; a woman who fears God, she should be praised.” I would not let vanity get the better of me.Over the next 10 years, I cycled through different stages and phases of hats. Hats for day and hats for night. Hats for summer, winter, and days it looked like rain. Hats for casual wear, formal, and in-between. Hats that were comfortable for a maximum of two hours and those that could stretch to four or eight. Kofias, eight-point caps, and bucket hats. I could have opened a millinery.Some, like my wide-brimmed straw hats, looked great on me. Others looked like a bird had been shot midair and plummeted earthward to land on my head.As the years passed, my frustration grew. The hats made my head itchy and sweaty. Unexposed to the sun, my hair lost its luster. The chafing of the material against my scalp seemed to expedite hair loss. I resented having to suffer this discomfort in order to quell men’s urges, particularly since I didn’t believe the hats were doing the job (more likely the weight gain of three pregnancies and dowdy dresses were sufficiently subduing them). But it didn’t matter how I felt, I reminded myself; I was not the final arbiter. I had to find a way to make peace with my mantle.Year in and year out, my hats and I wrangled. I had a short reprieve when I came across a quotation in the Talmud by Rabbi Huna Ben Joshua, a third-century sage, who said that he never walked four cubits with his head uncovered, “because the Presence is always over my head.” His proclamation is one of the sources for the custom of men wearing kippot. Rabbi Huna’s words resonated with me. Perhaps if I thought of my hats as a reminder of this divine presence, I would better tolerate, even appreciate them. Hair covering would have a meaning and purpose I could embrace wholeheartedly.Unfortunately, Rabbi Huna’s inspiration was short-lived. Within a matter of weeks, my hats did not remind me of the Presence any more than my socks did.I was uncomfortable and frustrated but not the kind of person who reneged on commitments. Besides, I was afraid of the slippery slope. What if the decision to uncover my hair was the insidious onset of a spiritual decline, an irreparable crack in the foundation? What if my children understood from my action that all of the commandments were up for grabs?Every once in a while, I’d bring up the topic with my husband. “I’ve had it,” I’d say. “I can’t stand it anymore.” I would have liked to cast him as the enemy, the one subjugating me by forcing me to wear hats. That way I would have had a target at which to mount my insurrection. But, too smart to take the bait, he calmly reiterated that he respected whichever choice I made.When I commiserated with my observant friends, many of whom were also baalot tshuva, they said they had grown used to covering their hair. The coverings had become an organic part of them, an extension of their heads, like a fourth meningeal layer. A few admitted to struggling with the hair covering, but accepted the yoke of the kingdom of heaven. On the whole, they seemed to have made peace with the obligation. Ten years had passed since I began wearing hats; it was time for me to make peace, too.Fed up with the struggle, tired of living in cognitive dissonance and faced with more pressing concerns—like raising three children and making a living—I decided to call a truce.Some of the Jewish laws I kept made sense, others didn’t; some were easy to uphold, others challenging. Yet they were all part of this way of life I had chosen, a set of values and traditions which linked me to a people and a historical chain going back 4,000 years. The hat on my head was truly a small price to pay to be part of this grand heritage.The truce held 10 years until the day intentionally left my hat on the passenger seat of the car to see how being hatless would feel. But another five years would pass until I left behind my hats for good.One day last year, I looked through family photo albums. In every snapshot, I saw myself smiling and looking up from under the brim of a hat. In some photos, the brim cast a shadow over my eyes. In others, the hat had fallen askew or my hand was laid flat against the top of my head to prevent the hat from flying off in the wind. In a few photos, I’d just taken off my hat and, hair plastered to my scalp, was indicating to the photographer, “please don’t.” I had shouldered the burden of hair covering for 25 long years. It was enough.When I turned 55, the fragile armistice between my hats and me crumbled. I stuffed my hats in a large orange garbage bag and dropped them off at a used-clothing charity.***How binding is the commandment to cover one’s hair? Whether it is a biblical or rabbinic injunction is a matter of dispute. What is indisputable is that the specifics of hair covering (where, when, how much, what style) have been determined largely by community standards.Women covered their hair in Talmudic and medieval times but there was a period in Jewish history, post-WWII, during which Orthodox women did not cover their hair. Today most do, but uncovering it is not such a stretch. We’re not talking lobster bisque or harlotry.Does anyone keep all 613 commandments? Excluding the ones from which we are exempt because they apply to the temple or the priestly class, don’t we all do the best we can? I suppose it is my misfortune that the mitzvah I find hardest to keep sits on top of my head in full view of others. If I had decided to take to checking my email on Shabbat, no one would know. My frumkite, at least its façade, would appear undiminished.I’ve made many sacrifices to live this Torah life: observing family purity laws, fasting six days a year, dressing in skirts and sleeves, to name just a few. I don’t understand or embrace every mitzvah I keep and that’s fine, because I acknowledge that each is part of an intricate tapestry that binds us as a people, distinguishes us, and brings us into a greater relationship with holiness. I’m willing to make sacrifices in order to live an observant life because I believe it’s the most authentic expression of Judaism and the most likely to survive.But I’m no longer sure that Orthodoxy is an all-or-nothing life choice. Observance is a continuum on which we each locate ourselves. Every one of us struggles to find a livable balance between personal freedom and submission to authority, commitment to self and commitment to other, even if that Other is creator of the universe or a long-held tradition. “In the end,” as my mother-in-law says, “everyone writes their own Shulchan Aruch.”I may be hatless today, but you won’t find me bareheaded on the street. Today I wear scarves, strips of colorful cloth wrapped in a band around the center of my head and tied at the base of my neck. I know the scarves don’t adhere to even the most minimal legal standard of hair covering. They aren’t particularly modest and don’t necessarily identify me as married or religious. It’s very possible they will, one day, go the way of the caps and berets. But I can abide them. And in some symbolic way, they tie me—by a thread, by a scarf—to the Orthodox life I have chosen and within which I struggle.***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.