A picture of eight-year-old me reigns supreme in my parents’ house: I’m wearing a tutu, my hair is in a chignon and I’m in the middle of a ballet class. Although I look delighted, as if being a ballerina was all I ever wished for throughout my eight years of existence, don’t be fooled: if memory serves right, all I wanted to do while posing for the photo was to scream and shout and rip my white tights off. All I can think of now while staring at the picture is how awful Mondays were throughout those years, when I had to push my legs through tights that still tickle my limbs at the mere thought of them, how uncomfortable I felt in a tutu and how I wanted to stab the teacher that worked on my hairdo with one of the 36 bobby pins that were jabbed through my scalp. But, boy, did I look good.

That’s the thing: when thinking back to the times I looked and felt good, memories are tinged with a bit of pain. The night of my sister’s wedding, my show-stopping Marchesa dress made it impossible to walk (a fact also due to the sky-high stilettos I wore that kept punching holes in the bottom of my gown). While traveling through Panama, Cuba and Greece, my go-to jumper, the one that screams “I look fabulous but can still properly peruse the town with this outfit on,” was weather- and photo-appropriate but incredibly inconvenient and downright inefficient when having to go to the bathroom, also getting itchy at random, sweat-induced times. Trying my best to look my best while preparing for our honeymoon in Japan, I packed my most stylish and vacation-appropriate boots, but my feet would throb with pain and pulsate with blood at the end of each daytime excursion, rendering nights out even more painful sessions of street navigation.

Alexander McQueen SS 2010

That’s all to say that thoughts of my personal feel-good fashion moments always show up alongside an agitated sense of dread, weariness and discomfort. I don’t think to be alone: the history of fashion is long and much chronicled, if not so much by words and historical factoids as by images. Page through old issues of Vogue, Harper’s Bazaar and Prada catalogues and realize that women especially have looked their most glorious in clothes that, when inspected up close, send chills down spines of those whose only shopping criteria is comfort. Sure, jeans, a white T-shirt and sneakers—the essence of comfort outside of the home—can look as stylish as a gown and stilettos, but there is something about dressing up that adds a level of art to getting dressed.

Take the high heel. The fashion symbol par excellence across most of the planet, the heel in its original form was not a strictly female-centric creation. In a recent article on The Guardian (“Sex, Power, Oppression: Why Women Wear High Heels”), Summer Brennan attributes the birth of the “modern elevated shoe” to Paris. “The first came in the 17th century at the court of King Louis XIV,” she writes. “When blocky talons hauts, inspired by Middle Eastern riding shoes, were deemed the best way for a nobleman to accentuate the muscles of his silk-stocking-clad calved and proclaim his status.”

A signifier of social ranking since its inception, the heel eventually became a solely-for-women daily garment in the 1950s, “when Dior designer Roger Vivier put steel rods into the shafts of skinny stilettos, raised their height to three inches or more, and encouraged regular women to wear them in daily life.” Brennan continues: “Thus, in the postwar era, when an emergency female workforce had recently been shuffled back to the kitchen, the template for the contemporary high heel made its debut.” Thus a status symbol was born and reshaped.

Maison Margiela SS 2009

Where are we now? Literally skyrocketing a body to new heights, the heel today is a mostly female-worn piece that catches people’s attention while shocking the wearer into extreme levels of hyper awareness: you never want to fall, after all. It might be painful, you might not be in the mood, but, most of the times, the discomfort pays off: people tend to look and feel better in heels, because the heel demands a physical presence by its mere construction that other shoes don’t. As Niala Boston puts it in a 2015 piece for the Odyssey: “Think of fashion like a superhero’s alter ego; it is not until Bruce Wayne puts on his mask and bat suit he feels like he can take on his enemies.” Might heels be our superhero attires?

Shoes are far from the only closet items that might beg to be ripped off: ever worn a tube top that requires constant jingling and repositioning? How about skinny, high-waisted jeans that feel like roadblocks to blood circulation? Let’s not forget about thongs and the let’s-wear-our-corsets-over-our-shirts trend.

In the postwar era, when an emergency female workforce had been shuffled back to the kitchen, the template for the contemporary high heel made its debut

All this begs the question: Is uncomfortable fashion the only way to be fashionable?

“I think style and fashion can definitely be accomplished without compromising comfort,” says Jamie Nematzadeh, who works in finance in New York City. “As women, we can make anything work, be it a muumuu, combat boots, sneakers and sweats. So, to feel like we always need to be in tight clothing and high heels to look good is wrong.” That being said, the power of a heel isn’t lost on Nematzadeh: “[I am dressed at] my most stylish outside of work. I work in finance so I wear business attire that I try to jazz up instead of wearing slacks and blouses all the time, but definitely my trendiest is when I’ve got some leather and heels and a pop of color.” As for heels in specific, “I wear [them] very often,” she says. “Every night I go out, sometimes at work and on the weekends. I’m short, and I don’t love looking short. I like to look tall and elongated, it lifts my butt and my confidence!”

Iris van Herpen X United Nude 2013

Jasmine Namdar, a mother of three who lives on Long Island, echoes Nematzadeh’s sentiments: “I really feel that you can tell a lot about a person by the way they dress,” she says. “The effort you put into [wearing] different pieces together really determines how stylish you are in my opinion.” Although heels aren’t a necessity according to her logic, Namdar still ends up rocking them “three to four times a week.”

According to Rachel Nabavian, a 29-year-old New Yorker, necessary discomfort can take a different form: “I feel the most stylish when I’m physically groomed, not when [wearing] a certain outfit,” she says. Although not necessarily “uncomfortable,” she finds the painstakingness involved in manicures, hair removal processes and hair salon appointments to be inconvenient and expensive—but a true sign of style. “When my hair is done, I can wear rags and look good,” she exclaims. “It’s about being confident and having good posture.”

One thing the three women agree on: no matter what they consider to be uncomfortable, they deem the discomfort worth the way it makes them feel.

Could the proclivity to ignore pain to look good be a cultural phenomenon? Born and raised in Italy by parents that were born elsewhere (my father, Tel Aviv; my mother, Tehran), I have rarely worn or noticed other people wear sweatpants outside of the house. My father doesn’t even wear them in the home he now lives in, in America, the capital of comfortable clothing.

Zaha Hadid 2013

“You’re going to have to suffer to be beautiful,” my mother constantly warned me. A devout wearer of heels who once went to look for “comfortable clothes” in Milan’s equivalent of a jazzed-up Bandier, Lululemon and Theory store wrapped into one, my mother recoils at the mere mention of a lack of effort when getting dressed for any sort of event, including school dropoffs. Is her attitude a result of the various cultures that shaped her earliest years? Nineteen-seventies Iranian fashion was heavy on the prints, the bare skin and western trends—a culture at odds with post-Revolution Iran, by which time my mother had already fled to America. A few years in New York did little to suppress her desire to consciously dress to impress (herself and those around her), still holding on to the styles that dominated Iranian magazine covers as she was growing up, my mother eventually moved to Italy, considered by many the capital of high-end fashion, where her disposition and acceptance towards garments that might not feel comfortable but certainly look glamorous took final shape. Although in New York for the past 14 years, she has yet to give up on that outlook and has imparted it, with the help of her ultra-glamorous husband, onto her four kids. So is my devotion to what I deem to be stylish, no matter the discomfort involved in having to rock said style, a direct result of my mother’s cultural upbringing?

The irony of talking about pain being a necessary part of beauty is not lost on me: we tell kids they’re beautiful as they are but, in the same breadth, we advise them that a bit of suffering might go a long way in turning them into really beautiful humans. Pain as a road to beauty is a dangerous notion when inflicted upon you, but when practiced with self-control and free will, it takes on a magical quality. When wearing heels is a decision that I make myself in an effort to take control—although I have no say in how tall I am, I can command how tall I could potentially be when wearing shoes—I might actually start feeling powerful and beautiful. Which means that our white canvases are beautiful, but we actually have control to shape that beauty however we want it to look like.

Winde Rienstra 2012

So I praise the beauty of the uncomfortable, especially now, while pregnant. Not in charge of my body’s fluctuations—beautiful, exciting and promising fluctuations that nevertheless don’t feel like myself just yet—I at least can exert control over how my shifting body is projected to the outside world: I choose to wear the overalls that itch my tummy yet show it off in elegantly trendy ways. I choose to wear heels, at times, because although I don’t have much authority over my weight at the moment, I can control my height. I can choose the discomfort that makes me feel most like myself, most like the beautiful version of myself I want the world to see when taking off the pajamas that I pleasurably rock throughout my apartment each night, which is still a comfort that’s sometimes absolutely necessary.