I have a dream. It involves waking up on the laziest of Saturday mornings, rolling out of bed and slipping into my favorite vintage Levi’s cutoffs, a pair of well-worn sandal slides and—most crucially—a slouchy V-neck cotton tee. One where the neckline dips below my clavicle and the soft, featherlight fabric nonchalantly drapes across my torso, the hem meeting my shorts in a coolly careless half-tuck. No bra. No problem.
Yet there is a problem. And it’s kind of big. Well, size 32D big.
The fact of the matter is, I can’t do the braless thing. Period. It’s been that way ever since I was a freshman in high school, when my tiny, five-foot-one frame started to develop a not-so-tiny chest. My mom’s first attempt to broach the elephants in the room hadn’t gone well: She presented me with a copy of My Body, Myself, which I proceeded to slam-dunk into my wicker trash bin. That’s how uncomfortable I felt about growing up—and out. Still, she insisted we take a trip to the Bloomingdale’s lingerie department at Sherman Oaks Westfield Fashion Square Mall in Los Angeles. There, I was measured as a B-cup and bummed to learn that my trusty Calvin Klein cotton training bras would no longer do the trick. Today, two sizes later, I still find myself looking longingly at lacy bralettes from Cosabella and Honeydew while readjusting my underwire. I need support. But my hope is that you’d never know it.
The people whose styles I admire most—the icons whose photographs populate my “I Like Your Steez” Pinterest board (@jennagott)—are, for the most part, the flattest of the flat-chested: There’s ’70s-era Jane Birkin looking willowy and slightly mod in a ribbed turtleneck, Charlotte Rampling wearing a romper layered over a chunky knit and Kate Moss modeling a pair of belted Calvin Klein jeans … and absolutely nothing else.
I love that pared-down, slightly tomboy aesthetic, and for most of my life, I’ve tried to keep my not-so-subtle curves from getting in the way of that. I’m obsessed with a low-key minimalist look, and I tend to prefer quiet hits of femininity (blocky heels, delicate gold necklaces, a swipe of mascara) to overt ones, like sweetheart necklines and push-up bras. Don’t get me wrong: I’ve never gone through a boob-taping phase, à la Christina Ricci in Now and Then, or even owned a minimizing bra. I don’t try to hide my body—I just don’t necessarily dress for it. In fact, one of my absolute favorite things to hear is someone exclaiming with genuine shock, “Wait, Jenna … you’re a D?!” as my coworker, senior beauty editor Maura Lynch, did upon discovering I was writing this very essay. “It’s just when I think big boobs, I think Scarlett Johansson or Christina Hendricks—you know, noticeable,” she explains. “Your chest doesn’t come off as prominent. It isn’t one of your defining features.”
Mission accomplished. Still, going for boyish chic isn’t easy when your boobs are constantly declaring you otherwise. Certainly, there are some pieces I can pull off with ease. My closet is stocked with starchy button-downs and boxy ’70s-inspired tunics. I love straight-leg, high-waisted mom jeans and regularly pair them with massive sweaters acquired from my brothers and ex-boyfriends. Some of my most prized possessions include a vintage schoolboy Brooks Brothers blazer and a Brooklyn We Go Hard sweatshirt, size men’s extra-small, and I think an oversize Barbour field jacket is the most stylish thing in the world.
But it can get tricky, especially as the weather warms up. Try tucking a silk popover into a high-waisted pair of shorts while working with size Ds. The effect is boobs on legs (or as I prefer to call it, 18th-century pirate wench). It’s a problem shared by Lucky deputy editor Leigh Belz Ray, whom I turned to for some sartorial empathy. “Summer in general is tough,” she confirms. “Triangle tops, back cutouts, floaty sundresses … The easier and breezier the garment, the more tactical you end up having to be.”
This year, with six weddings on my calendar between Memorial and Labor Day, I couldn’t agree more. While I yearn for the season’s gorgeous, gossamer slipdresses from DKNY and Narciso Rodriguez, on me they read less ’90s- ethereal, more scary uni-boob monster. The fact is, the cocktail-appropriate silhouettes I’m most drawn to—backless, strapless, plunging—are generally off the table for someone with my shape.
Unless a dress is made out of industrial-grade wet-suit material (or I find myself at a bachelorette party in Atlantic City), I require undergarments. I’ve learned to love wide tank- and tee-shaped fit-and-flare silhouettes, which effectively hide straps. And every time I attempt to deviate, I find myself in the dressing room thinking yet again, If only I didn’t have to wear a goddamn bra.
It doesn’t help that living in New York and working in fashion leads to envy-inducing encounters with many a free-boobing wonder. “I remember at my first job, a senior editor went braless half the time as the weather warmed up and I thought, She has no idea how good she has it,” says Belz Ray. I regularly glimpse models trotting around the city in nothing more than a muscle tee and a Technicolor bralette, worn strictly as eye candy and not out of actual necessity. And twice a year during fashion week, I view dozens of collections chock-full of innovative designs (those pleated Alexander Wang crop tops for spring 2014 come to mind) that I would love to add to my wardrobe—if it didn’t mean being cited for indecent exposure while riding the subway.
But then there are those times, every so often, when someone will remind me how good I have it. One recent Saturday morning, my close friend and trusted shopping buddy Robyn stopped by my apartment toting a slinky, sleeveless black Elizabeth and James midi dress she had ordered online. She had yet to try it on and admitted, “I actually feel like it would look good on you—let’s see.” I eyed the low-cut square neckline warily but obliged, thinking first and foremost of the aforementioned summer wedding circuit. Yet when I glanced in the mirror, I was surprised at how well the minimalist jersey style suited both my taste and body. Though simple, on me the dress didn’t look plain. It looked sophisticated and cool … and just the right amount of sexy. “See?” said Robyn. “You have the boobs for it.”