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Faux fur vest? No problem. Over-the-knee socks? Sign me up. But as sartorially adventurous as I am, I’m usually hesitant about wearing heels. At five foot eight, I’m already a full head taller than most of my girlfriends. Heels boost me up to six feet, which puts me eye-to-eye – or chin-to-eye, or even worse – with the guys I know. But I love heels. Honestly, I do. A very large portion of my closet is dedicated to my shoe rack, more than half of which is filled with heels. While I’m not quite at Carrie Bradshaw’s level yet (she reportedly owned four hundred pairs at $400 a pop), I do have quite an appreciation for shoes. I decided it was finally time to embrace my height and take a pair of my heels out for a spin on a casual day.
 

 
The shoes in question: A pair of black oxfords with a three-inch heel. I bought them on sale at H&M last year, and they’re surprisingly comfortable for the price I paid. I wore them with a purple sundress, a denim jacket, and a pile of vintage jewelry.
 

 
The minute I clack-clack-clacked into school, I wished I had a pair of flats stashed in my bag. I could see heads turn as I passed, often with a confused look upon their faces. But it only took me a few seconds to realize that trying to blend into the background was useless. If I was going to wear heels, I wanted to wear them proudly. I asked myself, “What would Carrie do?” So I straightened up to a full five feet eleven inches, put a smile on my face, and kept walking.
 
My Carrie-inspired confidence was tested early that day. As I stood practically eye-to-eye with my six foot-plus journalism teacher, he asked, “Are you almost my height?” I was immediately brought back to the scarring experience of my eighth grade semi-formal dance. While my friends tottered around in their first pair of pumps, I was already a head taller than my date. With Tom Cruise and Katie Holmes’s wedding fresh in mind – Tom had hidden platforms inserted into his shoes to attempt to negate the height difference between him and Katie – I felt like it would be a sin to intentionally make myself any taller than my date. Instead of wearing heels, I opted for a pair of leopard print flats. Thanks to the height issue at the dance, I developed an irrational fear of being taller than guys. My diminutive date made me feel like a giant by comparison. So when my teacher brought up my height, that feeling of insecurity I felt at the eighth grade dance came back to me.
 

 
But while I received a few odd looks in the halls that day, the majority of reactions were overwhelmingly positive. Most of my friends were supportive and encouraging, even the ones who don’t understand the allure of pretty shoes. One friend reasoned that I wasn’t overdressed because the shoes appeared casual enough to work as daywear. Another friend reassured me that I wasn’t too tall. As I walked into my Stats class, a classmate’s face lit up. “I love your shoes!” she squealed. “Where did you get them?” Confidence: boosted.
 
After school, I had plans to meet up with a friend at Starbucks to study for an upcoming test. The trek between school and Starbucks seemed too daunting to even consider, but the thought of a hot chai latte convinced me to start walking. Wearing heels in school is one thing; wearing heels on uneven sidewalks in the rain is something else entirely. I’ll admit, I didn’t suddenly turn into Tyra Banks overnight – I was ready to sit down and rest my feet by the time I got my latte – but my feet didn’t hurt nearly as badly as I expected them to. If hiking the half-mile from school to Starbucks in heels through drizzly rain didn’t turn my feet into bloody stumps, then I figured must be pretty invincible.
 
That night, I was working at a Boston Fashion Week show. I was assigned to helping dress models backstage and check guests’ names against the guest list at the door. I knew that fashion is one industry which, without fail, is always supportive of a girl in heels. But to my surprise, I was told right away to change into flats so I could help move furniture before the show started. Fortunately, I had a pair of flats in my bag by that point. As soon as the show started, I switched back into heels. In a room full of women whose feet have never touched the ground without a little Louboutin in between, I truly felt confident rocking my heels.
 
After a long day, I just wanted to change into a comfy pair of PJs and go to bed. But as soon as I took off my shoes, I found that I missed the authoritative clack as I walked. Surprisingly, I even missed the height boost. As I stepped into flats the next morning, I felt like I had literally stepped down a notch. Is it silly to admit that once I got past being self-conscious about wearing heels, they actually made me feel more confident? When I interviewed our school’s athletic director for an article for my school’s paper, my shoes helped me feel professional and put together. When I walked by girls wearing sneakers and Uggs, I felt like I was earning major style points. More importantly, wearing heels helped me come to terms with my height. Being taller than a guy isn’t the end of the world.
 
I learned more than I had expected to from this challenge. What I originally thought was just a challenge to get through the day entirely in heels turned into a lesson on self-confidence. Girls, hang up your insecurities about wearing heels. It doesn’t matter if someone else might think you’re over-dressed, too tall, too short, or whatever other crazy ideas they might have. If you have a fabulous pair of shoes you’re dying to wear, rock them! You might be surprised at how hard it is to make the switch back to flats.

Originally from Boston, Hannah is now a sophomore at New York University and loves life in the big city. Her favorite things include poking fun at celebrities on Twitter, yoga, leopard print shoes, Frank Sinatra, and her little sister Julia. Hannah was Her Campus's first editorial intern in Summer 2010 and has since continued her involvement with HC as the High School Editor and head of the High School Ambassador program. She is a former Seventeen and Huffington Post intern, where she researched and wrote about celebrities and once made lunch for Kylie Jenner. Read her short-form ramblings at @hannahorens.