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I Wore a Skirt for the First Time: Here is How it Went.

This article is written by a student writer from the Her Campus at UPR chapter.

My relationship with clothing is complicated. Much like the troubles I face romantically, I can’t find common ground when it comes to my body, dressing up, and trying to be as fashion-forward as I can. As someone who works in fashion, I find it completely troubling to keep up with trends, seasons, and a budget to be able to afford looking like I indeed work in fashion. 

Between events, money, university campus and my pressure to always ensure I look like an icon, dressing up has always been a tango I never seem to lead. And it hasn’t helped that working in fashion makes your insecurities about how you dress up stand out even more. I admit that past experiences in the industry have at one point or another made me lose my individual sense of style.

I’ve become terrified of wearing things I was once told were maybe childish, incorrect, or out of trend. 

However, as I move on and heal, I’ve tried to stay more in touch with my style, my body, and how I choose to dress. That being said, I was always curious about how I would feel wearing a skirt. Growing up and identifying as cis, dressing up in something that doesn’t confirm your gender identity can be a tricky situation. More than not knowing how to style a skirt to my body… I confess I was terrified of wearing it and being perceived differently. Would I not be taken seriously because I was wearing a skirt?

At the end of the day, it’s just a damn piece of fabric.

My first time wearing a skirt has two outcomes. The first one was a fashion gala. During the busiest and most iconic fashion week in Puerto Rico, I was invited to a prestigious designer’s event with a strict gala attire dress code. I knew the men in said event would follow the dress code and wear a tux with slacks. While I don’t have anything against that, I simply decided that I had to find a way to stand out amongst all the black attire. 

I decided to show up in a long A-line skirt with an open cut out blazer. How did I match the skirt fabric with the blazer? I have no idea. Without any precautions I strut my way into the gala with a skirt and the rest is history. I felt amazingly confident and comfortable wearing this outfit in public. It got a lot of praise and led to some high industry people to notice me and talk to me. The stares of late generation people were normal; some even made double takes of my outfit. Without a doubt, my outfit was the signature cocktail of the night. 

The overall experience of wearing a skirt to this event was amazing. I stood out and felt confident while doing so. Above all, I had challenged myself to wear something that terrified me. However, I felt the experience was too easy or I at least embraced it the way I was expecting to, because at the end of the day it was a fashion event. These kinds of statements are expected and praised. 

The real challenge was wearing a skirt on a normal day, without any justification or fashion event to hide under.

A few days after that industry event, I wore a skirt I bought at Zara. With a similar length to the one I wore to the fashion show, this skirt was made in a bulky yet comfortable material for everyday use. Which is why I decided to wear it for a long day on campus.

I get up really early to go to campus. Traffic is no friend for someone who never knows what to wear. However, that morning I was clear on what I was wearing. I paired this new skirt with an oversized t-shirt and some sneakers. I looked in the mirror and felt pretty normal. The skirt would do all the talking about my outfit. I cat walked to my car and I was ready to conquer the day… Until I had a little car accident just driving out of my house. 

When I realized what had happened my first thought was: “Now I gotta go face whoever I crashed into wearing a skirt… this won’t be pretty”, and it kinda wasn’t. While no one and no car was harmed because of my questionable driving skills, the man I hit was quickly outraged when he saw me… and we all know it wasn’t because of the scratch I left in his car. When he stepped out of the car the only thing he saw was my skirt. He constantly scoffed at himself after staring at my skirt. He treated me like a child and even threatened me if I didn’t take the situation seriously. He said all this by constantly looking at my skirt.

Thankfully, the accident happened in front of my house and my mother quickly stepped out to see what happened. After he saw my mother, he calmed down and was more open to talking on a peaceful manner. After addressing the damage, we all decided to do the standard police report to claim insurance for the damages made. Once we decided to go to the police office, my first instinct was to change into a pair of pants… and I did. 

Once I stepped out in pants, this man actually looked me in the eyes and made a casual conversation with me. He even asked if I was okay, something he didn’t do when I was in the skirt. His whole interaction with me changed once he didn’t see me wearing a skirt. When I realized all of this, not only did I feel completely uncomfortable with him… I was uncomfortable with myself. Why was I scared to carry on with the day wearing a skirt? What about those people who feel horrible in pants or gender normative clothing who have to endure what this man did or worse in order to dress in clothing they feel like themselves in?

I felt completely disappointed in myself. While I’m thankful I was able to change into other clothing and still feel comfortable, I hate the fact that I was taken more seriously wearing a pair of swim trunks than the actual skirt (which was really cool). 

After the whole police report was filed, the man went on with his life and so did I. I decided to still go to campus since it was still early and I had only missed one class. I put the skirt on, and yet again, I felt completely terrified to wear it. 

I got to campus, and I got a few looks. I even saw people who laughed as they walked past me, and some even looked confused. However, there were a lot of people who came up to me and said that I looked cool. People who know me and love what I wear thought the outfit was up to the standard of how I usually dress and my friends treated me like it was any other day. 

What I take from the experience was the challenge and the embracing of change. We’re so used to always doing and wearing the same thing. Clothing should make us feel comfortable and confident, but it also has to challenge us, to try new things. As someone who strives for innovation, I have to understand it sometimes comes from the little things we do to ourselves that eventually fuel our great ideas. I won’t apologize for wearing what I want, especially if I look and feel amazing in it. If you want to wear it, wear it. It’s just a damn piece of fabric. 

José is majoring in Public Relations and Advertising. This communication undergraduate student from the UPR Río Piedras campus is an energetic Pisces with a passion for fashion, coming of age films, books, crossfit, and dance. Currently, José is a writer for HerCampus and the editorial executive and digital content creator for fashion magazine Imagen and lifestyle magazine BuenaVida.