Two weeks before my son’s 16th birthday, after shrugging off my suggestions that we do something to celebrate, he emailed me a wish list that included $350 sneakers. The apparently coveted Y-3 Retro Boost looked, to me, exactly like regular black sneakers with white soles, but also included some complicated loop at the heel.

Perhaps I should have been appalled, but I was not. Or rather, I was appalled but not surprised. The tension over what to buy and what not to buy started the Halloween he was 5. I knew Prefab vs. DIY was not a new or original generational battlefield, but I also thought relenting with a store-bought Flash costume would gain me some leverage (i.e., pick your battles). I was 23 when he was born, too young to understand how little control I would actually have as he grew. My son’s father and I were living in rural India when I’d gotten pregnant and returned there after our baby turned 1. I had not had a thousand-dollar stroller or a designer layette. Instead, I had 12 cloth diapers we washed out at the hand pump. Because we’d spent so much of my son’s early years avoiding American consumerism, I was shocked to see how quickly it surfaced once we were back and how unequipped I was for all the judgment aimed at me for what I bought for my son or didn’t.

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Which is to say that as he’s grown, the stakes have gotten higher – more expensive and more emotionally loaded – and I still don’t know what the right thing is. Because just avoiding this pair of $350 sneakers doesn’t solve the problem of trying to raise a self-reliant kid at a time when we’re all bombarded with the capitalist mantra that products are, in fact, essential to our sense of self and self-worth.

My son is a sensitive, observant boy with a kind heart and a sharp sense of humor. He takes good care of his little sister, is respectful to his teachers, and worked hard this summer at his first job, “landscaping” (or picking up trash) at a local park. But, born in 1999, he is also very much a product of his generation, who, in a sweeping generalization that also feels quite specific, seem to exist on this fulcrum between consumerism and technology – using their phones to trawl for products, to buy the products, to post pictures of the products on their phones.

In addition to my angst over increasing sweatshop labor, corporate profits and landfill waste, I lie awake in the middle of the night most anxious about something that happened when my son was about 10: he explained his certainty that an expensive watch would make anyone happy. “If you had that watch, people would want to be around you,” he said with the logic of a child who was hard at work interpreting the world around him. Which is exactly why I know that he can hardly be blamed for emulating the very principles of the wider American culture in which he’s been raised.

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In the spirit of full disclosure, I will admit that as a 6-year-old in 1982, I named my tabby cat Gucci after a classmate’s father traveled to Italy and brought her home the purse our second-grade class agreed changed everything. As one of only a handful of lower-middle-class kids at my private, all-girl Catholic school, I got an inadvertent crash course in expensive preppy. It was also the 1980s, when the whole U.S. stopped going to church and started going to the mall instead.

But raised on equal parts Catholic guilt and Protestant work ethic, I also grew up ashamed about wanting the things I did. My grandparents grew up during the Depression and 50 years later, thrift was still promoted in my family not only as practical, but as a display of national, even ethical pride. When my grandma explained that she had to forgo both piano and ballet lessons, unlike her older sisters, I interpreted this to mean that self-denial equaled a kind of moral superiority. And even though the girls in my Catholic school evaluated one another’s ESPRIT quotient on a daily basis (uniforms, by the way, do nothing to curb judgment or meanness), our teachers, all nuns, worked tirelessly to bring the realities of the Central American poor into our classroom. Every week, we donated extra milk money to the street children of San Salvador. The way I learned to pray had very little to do with God and everything to do with recognizing the suffering of others.

While I am grateful for to have been raised with this hazy awareness of privilege, which did keep my own mother’s anxiety over the grocery bill somewhat in perspective, other consequences have included a lifetime of tormented indecision. I have a really hard time spending money on myself, even when it comes to socks and winter coats. Meaning that on top of the already fraught combat zone of teen materialism, in trying to figure out what to buy for my son, I’m also trying to get over my own vexed relationship with buying anything ever.

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Our family listens to records on a record player, sits on chairs found on the street, and makes calls on a rotary phone. For reasons beyond my parsimonious childhood, I believe in frugality and things that last, in flea markets over Ikea, in resoling my clogs rather than buying new ones. We don’t own a TV, a microwave, or video games. I say these things not with pride or a misguided confidence in their impact, but as context. As testimony that my son has not been raised with a bottomless allowance or spoon-fed luxury.

But in my deepest moments of self-doubt, I worry that upholding my values has actually fueled my son’s determination to reject them or, like any kid experimenting with self-definition or rebellion, to at least look elsewhere for fulfillment or individuality.

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When we were in Paris the summer he was 11, my son complained more than once that everything was “old.” Back in India the summer he was 8, he couldn’t get past how “dirty” and “broken” everything was long enough to see anything other than the poverty. In both cases, I couldn’t really argue – Paris is indeed old; much of India is dirty. And yet, I was still surprised to see how deeply ingrained the American ethos of "new equals better" was.

So while I’m ashamed to admit I would even consider $350 sneakers for anyone, especially a 6’1” growing teenager, I also worry that denying him the shoes make them that much more alluring. It’s a sort of damned if you do, damned if you don’t scenario – force your kid to stay too far outside the mainstream and you might make him a zealot. But let him embrace it and you create another mindless consumer.

In 2004, the American Psychological Association pinpointed the increase in marketing directed at teens as having a profound effect on how kids forged an identity and grappled with the vulnerability of adolescence. Advocating for more empirical research in order to push for federal oversight of commercial marketing aimed at children, many concerned psychologists voiced an urgent anxiety over the ways in which teenagers were persuaded to establish “brand loyalty” from younger and younger ages. Dr. Susan Linn, of the Harvard Medical School, said at the time that “comparing the marketing of today with the marketing of yesteryear is like comparing a BB gun to a smartbomb.”

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Eleven years later, the smartbomb has become a nuclear meltdown, with radioactive fallout landing in places we never would have imagined. When Kylie Jenner turned 18 this summer and received an $11,000 Birkin bag as a gift, 1.3 million people “liked” her Instagram post of the purse (to say nothing of the Ferrari she also received). While none of that would normally register on my own metric as relevant, I know for a fact that my son, who attends (public) high school in lower Manhattan, has spent many a lunch period loitering outside the Trump Soho hotel, staring hard at every black Escalade that pulls up, hoping for a Kardashian sighting. To this, he also feels entitled. Of this, he also imagines something meaningful.

Dr. Ellen Jacobs, a Manhattan-based psychotherapist who often works with families around issues of consumerism, agrees that the teenage demand for designer products has been steadily increasing over the last decade. Like everyone else, she also underscores the role of technology in drastically changing what kids are exposed to and their desire to acquire it. Celebrities and their wealth are “infiltrating our culture,” Jacobs says, and we’re all buying into it. “Everyone has a Louis Vuitton bag these days, whether they have money or not.” Or at least, that’s how it seems, because if you do have a bag, you’re publicizing it on social media.

As for how to respond to this shift as a parent, however, there is no silver bullet. Jacobs encourages parents to empathize with their children while also setting limits, which, she says, need to start well before adolescence. Giving to charities and volunteering can help counterbalance the impulse to spend, too, she points out, as does opening a bank account, to make real the satisfaction and practicality of saving money.

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In "The Opposite of Spoiled," New York Times financial columnist Ron Leiber also advises parents to engage their kids in fiscal literacy from a young age and to speak frankly about costs of living. In a section of the book aimed specifically at teens, Leiber describes the “Materialism Intervention,” based on the brainchild of a nonprofit organization called Share Save Spend, which encourages kids and families to think of their money in those three categories. Most interesting to me is a study Lieber cites, conducted on two groups of teens, one that was guided through the share, save, spend model and one that was not. Not surprisingly, the kids who adopted the program showed “better self-esteem” than before the intervention.

I champion all this advice as logical and necessary and actually plan to make some “share,” “save,” and “spend” jars at home. But I also bristle at the claims that individual families are solely responsible for, or even capable of, undoing all the vapid promises of finding contentment in new shoes, promises heaped on our kids from every direction. Precisely because this message is as pervasive as it is destructive, I want to partake in something far more radical than opening a bank account or curbing what the tooth fairy brings. I want collective refusal. I want political attention paid to the adolescent health crisis of the isolation that comes with spending hours a day on a device. I want celebrities who endorse the opposite of lavish as chic or heroic. During WWII, Rita Hayworth looked beautiful and conscientious in photos promoting national scrap metal recycling. Rationing efforts then were patriotic.

I recognize my responsibility to teach my son fiscal responsibility. And to describe the direct impact the global rise in capitalism has had on destruction of the environment. I know it’s my obligation to help him recognize that shopping doesn’t bring anything more enduring than the urge to keep shopping. But I also wish that we were having these conversations as part of and against the backdrop of much more public and dramatic action, education and debate.

Recently, my son took a class entitled “Economic Doomsday,” which included an overview of the housing crisis. For the first time in his life, he came home wanting to talk about who had what and why. Fortunately, he had a great teacher and, in the midst of SoHo real estate insanity, an up close and personal look at the multimillion-dollar penthouse getting built across the street from his school. But I also suspect that he grappled with the topic as thoughtfully as he did precisely because the lecture didn’t come from me. Which is why I’m still not convinced that refusing my son’s occasional request for big-ticket presents will result in anything other than resentment.

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In the end, I compromised, at least with myself. I didn’t buy the sneakers, but I did get him a gift certificate to Barney’s for almost as much money. While this solves exactly nothing, I am introducing him to buying on clearance. Hoping he might begin to ask more complicated questions about value and worth the more he’s in charge of his own money and his own wardrobe, I have to hope the critical conversations around our dinner table will echo back eventually. In the meantime, he’ll dress for his Kardashian sightings, not picking up when I dial his cell from our rotary phone to ask what he’s doing.