The Outfit You Regret Loving

We all have at least one article of clothing we cringe at when we remember the precious money we wasted on it, one horrid-looking jacket or a pair of boots we wish we never wore.

I can assure you, you’re not alone.

But, what if we stopped cringing at the shameful fashion moments of our past and started appreciating them for what they really are— agents of growth, shaping us into the fashionistas we are today.

Exhibit A: Me

I loved my brown boots. Styled with polka-dot leggings and paired with one of my many headbands, placed right on my hairline like Wonder Woman, my outfits were a messy sight to be seen. I was about eight at the height of this fashion ensemble, and about a decade later, I still gasp a little when I see a picture of myself at that time.

Image Courtesy of Angelique Rodriguez

Image Courtesy of Angelique Rodriguez

Image Courtesy of Angelique Rodriguez

However, I began to think: Who would I be without my precious boots? How else would I have developed my sense of individuality, one-of-a-kindness, and forever love for patterns, if not for eight-year-old Angie’s fashion sense? I realized it was necessary that my parents let me choose my own outfits and take an insane amount of creative liberty.

I also realized I wasn’t alone in this; everyone has their own cowboy boots, polka-dot leggings, and weird headband placement.

Looking back, polka-dot leggings and cowboy boots are a total fashion crime. But, I still reach for them today– just with better judgement. 

Image Courtesy of Angelique Rodriguez

Image Courtesy of Angelique Rodriguez

Exhibit B: Maddy

In middle school, Maddy was fascinated with the alternative style. She wanted to be as colorful as possible. Layering, heavy accessorizing, and baggy graphic t-shirts were some of her favorite style elements. According to her, it looked something like this:

Image Courtesy of Maddy Specyal

While she cringes looking at her Minecraft t-shirts in her hometown closet, Maddy can’t bring herself to throw them away. They made her comfortable, and layering them with her colorful undershirts made her feel seen and unique. 

Her alternative style was accompanied by an alternative lifestyle— it was an expression of rebellion and politics during her free time, until she had to step back into her private school uniform. It was individuality and lack of constraint. Years of memories stick to those t-shirts.

Maddy is still an alternative fashionista today, just in a slightly different way. She has a forever love for layering, but now sticks to earthy tones. She still loves experimenting with her style and trying new things; for example, she recently discovered long skirts compliment her height and figure. 

Image Courtesy of Maddy Specyal

Without those years of questionable style choices, Maddy wouldn’t have layered her white long-sleeved top under her denim vest, paired it with a vintage floral maxi skirt and wool cardigan and created a beautiful, stylish ensemble. And, were they really questionable choices if they led her to  the experimental, creative person she is today?

Exhibit C: Aaron

When he was younger, Aaron found it hard to find clothes he liked on himself. Nothing felt “right” on his body. He owned slim-fit jeans and hated them. Conscious about his weight, he experimented with different types of outfits and often turned to baggy shirts and shorts for comfort.

When he looks back at photos of him in these matching sets, he recalls  how they were the only pieces he felt comfortable in, flattering the places he felt slim jeans squeezed him too tight. 

He also had a brown suede pair of sneakers he wore with his baggy shorts. Today, he still loves suede; he often styles his brown suede tote bag with brown Birkenstocks that, according to him, match perfectly. 

Image Courtesy of Aaron Zagal

Now, although Aaron hates those cheugy sets he wore, he still loves matching when picking out outfits. He finally discovered straight-fit jeans and now wears pieces besides sweatsuits. He learned about silhouettes and proportions, and he pays attention to which colors and accessories compliment him best. 

Aaron needed those two-piece sets and slim-fit jeans to discover what made him feel the best in his own skin… and what didn’t.

Image Courtesy of Aaron Zagal

Everybody has a pair of polka-dot leggings, a cringey graphic t-shirt, or a sweatsuit. Most of us ughhh and yikes when we look back at them, but we fail to realize that they were formative to our self-expression today.

Style development starts at an early age. Like everything in life, mistakes and questionable choices are catalysts for  growth. The only difference is that clothes are easily documented on our parents’ Facebook pages or placed in our hometown closets— places where we can’t bring ourselves to throw them away.

At the end of the day, I’m thankful little Angie had such a vision for herself. I mean, the headband placement was totally unprecedented (maybe I’ve always been a trendsetter). Maddy is grateful she experimented so much with her style, and Aaron appreciates that his younger self  found an alternative to denim.

So, maybe it’s time to put down Pinterest and start using your awkward, messy, embarrassing childhood style choices to guide how you express yourself today.

Strike Out,

Writer: Angelique Rodriguez

Editor: Ria Pai

Angelique Rodriguez is an editorial writer for Strike Magazine GNV. Her favorite things: the color purple, any Drake song, and butterflies. When she isn't consumed in her writing, you can probably find her watching a romantic comedy, flipping through a Vogue magazine, or getting ready for a party. You can reach out to her by email @angeliquesrodriguez08@gmail.com or on Instagram @aangierrodriguez.

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