I’m 36 — when do I have to give up crop tops?

As a pre-teen in Y2K, the (small) shadows of crop tops loomed large. They were an inescapable fixture of red carpets and pop culture: Keira Knightley paired them with impossibly low-slung pants and Aaliyah with Tommy Hilfiger boxer-briefs, while the cast of “Buffy” battled vampires in short sweaters and tanks. In a decade when unforgiving low-rise jeans were the norm — and criticism over women’s bodies perfunctory — crop tops were not casual, easy wear; any softness of the torso was considered an aberration. I came of age on celebrity magazines and early gossip blogs that trained my eye to notice even the smallest deviations from thinness. You had to earn your stomach before showing it off.

Because of this, what should have been my halcyon midriff-baring years were not: I spent my teens and twenties both underweight and insecure, in a silent war with my midsection. It has never been firm, but curved, both from a protruding ribcage and a soft belly that may fluctuate but never flatten. By college, I was checking myself in every passing reflection, and strapped wide belts around American Apparel dresses as makeshift shapewear. I also believed that my window to wear more skin-baring styles was limited — after all, women’s desirability abruptly ends in our thirties, right? I felt as if I was quickly running out of time.

Like many women who return to old images of themselves, the body dysmorphia has cleared in hindsight. Why did I spend so much energy berating myself at my skinniest?

Now that I’m 36, crop tops have become an unlikely staple in my wardrobe, and I’m reluctant to let them go. I wear them casually for dinner dates, dress them up for nights out, and even have longer cuts with high-rise pants that I get away with at work. I find comfort and confidence in wearing something regularly that younger me would have balked at; it’s a small rebellion to reset the part of my brain that compulsively checks my stomach.

Cropped shirts began making my way into my wardrobe at 31, after several major upheavals caused me to rebuild my life in the way that I saw fit. They are emblematic of my greater sense of self-worth — a feeling I’ve noticed among my friends, too, as we emerged from our twenties with a more solid sense of ourselves.

I know now that my sense of aging even a decade ago was warped. I dreaded entering my thirties, but they’ve been by far the best years for my confidence. Even still, I occasionally wonder if there’s an expiration date to my favorite cut. Can I still wear crop tops in my forties? Beyond? I have the same questions about many things in my wardrobe that read too young or too much as I approach middle age (see: Dr. Martens clompers, over-shirt harnesses, flouncy mini-dresses, the list goes on.)

I am far from the only woman to question how to dress myself as I age, and, in fact, I have an easy blueprint to follow in my own family. I’m the same age now that my mother was when we relocated from small-town South Carolina to New York City, and — also undergoing a host of major life changes — a new world opened up to her. Though she had to keep a professional wardrobe as a real estate agent, after hours she had more fun. She happily adopted New York’s all-black uniform with leather jackets and chunky boots, and occasionally fishnets, too, as she became a backup vocalist for a downtown band called Housewives on Prozac.

At 10 years old, I was outwardly embarrassed (but inwardly, envious) of having a mother who was clearly cooler than me; I drew the line at her inheriting my electric blue platform sandals my grandfather bought for me in Chinatown after I outgrew them. Still, I also remember her own insecurities distinctly, and the body-checking habits she passed down to me that I’m sure she thought were discreet. Onstage with the band and, later, her one-woman cabarets, you would never know it. She exuded a sense of self-possession I’ve never quite mastered in any area of my life.

I know now that even though she was my mom, she certainly wasn’t old — I imagine this realization hits everyone at one point or another as they find themselves suddenly their parents’ age. Now I have a five-year-old stepdaughter (who, hopefully, is still a few years off from being embarrassed by me) and two nieces entering their pre-teen and teenage years. All of them already have very distinct senses of style, but I worry they will also grow up in a terminally online and unforgiving world that will damage their self-image. How can you grow up feeling good about yourself in a society oversaturated with digital (and real) nips and tucks?

What I can do is set an example, and try to build them up so that it doesn’t take until their mid-30s for them to be at peace with themselves. I can also keep wearing crop tops for as long as I feel like it — after all, whenever I see a woman a generation ahead of me owning her personal style and at ease with herself, it gives me something to aspire to.

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