That's Me, wearing heels to school every day.

Growing up in a small, rural town with a heart beating for city adventure, I would do everything I could to make it clear that I didn’t “belong” in Belmont, New Hampshire. Many teens rebel with piercings and cigarettes...I rebelled with high-heels.

Here I am pictured in 2011 during my senior year in high school. I loved collecting heels.

I was the only kid in my high-school who wore heels. Among Timberland boots and Converse sneakers, my shoes were an audible “click-clack” down the halls. At first, people would always ask me, “Why are you so dressed up?” But eventually, everyone got used to it being “my thing.” I was proud to have a sense of style in a place where people thought “fashion” was wearing the same Abercrombie shirt as your best friend.

In my heels, I not only looked taller, I felt elevated among people I’d judged as underachievers. In my 15-year-old-mind, if you didn’t desire to get out of Belmont, go to college, and have a career, it must have meant you didn’t have aspirations. My idea of success came from the actors, models, designers, artists, musicians, and writers I saw in my magazines. I was the kind of perfectionist who planned her life 20 years in advance and imagined it panning out like a “working girl in the city” narrative, circa 1960s in “That Girl” or circa 1990s in “Sex in the City.”

In my last year of high school, I would get terrible foot and shin cramps when I’d get home and take off my heels. Sometimes I would lie paralyzed on my couch for what felt like five straight minutes (in reality, it was probably 30 seconds), waiting for the agonizing sharp pain to subside.

That’s the ironic thing about trying too hard — it eventually gets so painful that it can paralyze you.

I went to college in Boston and soon realized the basic daily requirements of living in a city: walking on uneven concrete and cobblestone, losing count of all the staircases you climb, and the risk of catching a heel in metal grates. I began rethinking my strategy — the more I lived the life I’d always dreamed of, the more it required function over form. Heels would not get me through long days of classes, running around at internship events, or standing on a sales floor for six hours.

I began to favor ankle boots with thick, sturdy heels and sneakers that could look just as cool with a dress at Fashion Week as they did with jeans on campus. It was through this footwear evolution that my mindset also began to shift. It occurred to me that I had not only held myself to unreasonably high standards, but that I could stand to let up on the world around me too. What I view as success, style, and hustle won’t be the same for everyone else. As I grew more open-minded, sneakers naturally found their way into my wardrobe staples, pushing out most of my cramp-inducing stilettos and wobbly platforms.

By the time I moved to New York City, I knew fully well that heels would be a “special occasion” shoe, but wouldn’t provide the stability I needed to keep me grounded in a giant, dirty, congested, mecca of overachievers. It’s a city of great  opportunity, but that opportunity often feels unreachable. You see thousands of open doors, but they’re all 50 stories high and there are 50 thousand people reaching for them right next to you.

In New York City, I walk fast and travel prepared (seriously, I carry hand sanitizer, nail clippers, ibuprofen, bandaids, and safety pins in my bag at all times). I don’t have time for heels — they slow me down. I appreciate the comfort sneakers give me to walk around all day, at my usual swift pace, while also being able to take a detour and explore if I so desire. And that’s how I’d describe my current lifestyle — busy, yet not focused too much on what’s ahead. I prepare for the possibilities of tomorrow, but I no longer have a 20-year plan. I like to enjoy each moment as it comes...and that’s difficult to do when I’ve been wearing 4-inch heels for hours.

About the Author

Jennifer is a writer and editor living in New York City, who is inspired by people's individuality and creativity. She loves hunting for vintage treasures and will walk into a thrift store over and H&M or Zara any day.

Sunday Style is a New York City based digital publication on personal style.

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