My Complicated Relationship with Fashion Through the Years

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There have been lefts, rights, and u-turns during my style evolution.

Me laughing at some of the outfits you’re about to see.

If we looked at our 20 year history, fashion and I would totally have “it’s complicated” as our Facebook relationship status. 

The truth is, my style has changed a lot over the years, sometimes veering into strange territory — but would it be a real fashion journey if it wasn’t a little unconventional? With that said, today I’m going to take you guys through my style evolution — from elementary school to now. Oh yes. 

Warning: There will be photos of old me here. Proceed with caution.

My Youth: It all starts with Mama

I would like to formally thank my mama for being the catalyst to my fashion journey.

Just being your average Cynthia, drinking some Cola

For most of us, our parents/guardians gave us our first tastes of fashion. My mom is definitely the reason I know anything about style. She used to dress me and she did a really good job at it. In particular, I had a wardrobe full of pretty little dresses for church.

My mom believed, as she still does today, that when you go out, you should look always look your best. So even if it was a little party or church service, she would make sure I looked GOOD. 

I think another reason why my mom put an emphasis on dressing well is because we are African. I can’t speak for all countries in Africa, but where my parents are from, looking good is a big deal. We have these lavish dresses with beautiful details and designs and everyone looks great. So I believe that mindset went into how my mom would dress me. 

Though we currently butt heads on what I wear, I have to credit my mom with starting me on my fashion journey. Psst.. don’t tell her but I occasionally steal some of her older pieces to incorporate into my style now.

Despite mom doing her best to dress me, there came a time when I said enough was enough. I wanted to be my own woman. I wanted to dress myself. Which brings me to the dreaded middle school stage.

Middle School: What a Time

Why did my school colors include bright orange?

If middle school wasn’t a rough time for you, did you really go to middle school? 

As we all know, middle school is a time that we all wish we could wipe from memory. This goes for the clothes, too. Like every other awkward 12/13 year old, my fashion sense was an ongoing experiment. Most of my choices stemmed from trying to be like everyone else. I wanted to look like the other girls in my school, and step one was dressing like them.

I remember that I would spend a crazy amount of money on clothes just to keep up with all the cool people. Hollister, Abercrombie, and Aeropostale were big during my middle school days, and though they were expensive, I always found a way to get those things. I dropped $$$ on name brand jeans.  I bought Uggs just because other girls had them. 

I would never do any of those things now but that’s the price I paid to “look cool”. Like I said, I’d rather forget my middle school style. But here are some embarrassing photos anyway:

This couldn’t be a more bland outfit. 
At least my knees weren’t ashy.

My middle school fashion experience was characterized by materialism and not being comfortable with myself. Though it was a sad time self-esteem-wise, things began to change as I transitioned into high school. As you will find out, I started to improve my style but it was still stemming from a bad place. 

High School: Opinions Mattered

Me thinking this weave and pose were cute

One day after shopping, I remember telling my friend that I hoped my classmates would like my clothes. This says it all about my high school fashion philosophy.

In short, I cared WAY TOO MUCH about what people thought about me in high school. Low self-esteem coupled with wanting to go to fashion school dictated the way I dressed. At my school, people knew me as the girl who dressed well. I took fashion too seriously. Because I wasn’t popular and wanted to be liked, I thought if they don’t like me for me, at least they’ll like my clothes.

In this stage of my life, my style was really girly and business casual. Every day, I made an effort to dress up. I wore a lot of dresses, lighter colors like pink, and even wore heels at times. (Spoiler: This is the complete opposite of who I am now.) Pretty much all of senior year, you could catch me in my signature gray blazer from Forever 21. One of my friends said I looked like I was going to a job interview each day. I was the definition of extra. 

I think I went through a floral phase

In short, my high school style was all about trying too hard. And you can guess how that went: My clothes didn’t make me any friends and I knew deep down I wasn’t being myself. 

All I can say is, thank God for college. 

College: Loving How I Dress

I have a mom jeans and funky shirt collection!! You can tell I’m truly happy.

The glo up in my outfits is REAL!! My outlook on fashion is completely different today. I dress for myself and it feels good to be in this state. I wear what makes me happy because that’s what fashion is supposed to be about. It’s an extension and expression of who you are. My clothes show the world who Cynthia is and that’s how it should be.

Right now, I don’t have a specific style. I wear what makes me comfortable. I love relaxed-fit pieces. I wear things like oversized men’s jackets/flannels, mom jeans, funky button-ups, or whatever floats my boat that day. I rely heavily on thrifting.

Of course a denim fanny pack complements a thrifted denim dress

I’ll say it loud: I LOVE TO THRIFT.  My wardrobe is full of vintage pieces. My love of thrifting is not only about finding clothes; I enjoy the experience of sifting through the racks, searching for gems. It’s an adventure. Also, I don’t love spending tons of money on clothes, unlike my middle school self. With thrifting, I get to look cute for much less.

Cardi B makes me pose like a boss. Also, this denim jacket was only $12 at T.J.Maxx…a steal!!

That brings us to today. Of course, I wouldn’t say that my style evolution is complete yet. And that’s the cool thing about fashion: It’s always changing and it allows you to be who you want to be. This journey will always be weird but I’m happy with the pit stop I’m at right now. I’m dressing for myself and that’s all that matters.

Thank you for reading! 

Do you have a similar journey with fashion? Is it complicated? How did you dress in middle school and high school, and how does that differ from your current style? I would love to know, so leave a comment!

Source: #Fashionblogger #fashiontrends

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