The Evolution of My High School Style

From cringe-y freshman to fashion student in just four years.

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How my style evolved in high school

Four years ago, a naïve high school freshman, clad in (gasp!) low-rise jeans and flats, discovered her first pair of high-waisted shorts, and her life was never the same. That freshman was me.

Flash forward four years, and now I write for College Fashion and I’m on my way to study fashion in college. So, how did this happen? Let me take you on a journey…

Freshman Year

Style Evolution Freshman Year

  Product Information: Shirt, Jeans, Scarf, Cardigan, Flats

My closet freshman year was pretty much filled with 20 versions of the same outfit. I like to refer to this time in my life as B.H.W, or “Before High-Waists.” Like a cartoon character, I wore flats, skinny jeans, and a v-neck almost every day. When it got chilly, I added a cardigan or a scarf. When I ran out of cardigans or scarves I hadn’t worn lately, I borrowed them from my best friend.

While I’m sure we can all appreciate a good v-neck or pair of flats, this repetitive and trend-less outfit is not the epitome of a fashion icon.

The Lesson to Take to College:

Your best friend is a great source for clothes! When my best friend and I went to different high schools, we stayed close by sharing clothes. It doubled both of our closets, and when one of us went shopping we both got new clothes. Pretty sweet deal right?

Since you’ll have friends living in the same building as you, sharing clothes is that much easier. Oh, and bonus lesson? If you’re going to wear flats every day, own more than one pair so they don’t get scuffed beyond wear in a matter of weeks.

Also Read: Throwback Chic: Reviving 2000s High School Fashion with 20 Closet Must-Haves

Sophomore Year

Style Evolution Sophomore Year

  Product Information: Shirt, Jeans, Backpack, Gold Rings, Silver Rings, Shoes

My era of “After High-Waists” began sophomore year, and I’ve never looked back. In addition to high-waisted jeans/shorts/skirts, I wore a lot of band t-shirts and funky vintage button-downs. This was also around the time when I started wearing 1,000 rings (borrowed from my mom, of course).

I played a lot with discovering different ways to wear things, like knotting a big t-shirt to make a crop top, or layering socks under boots so they peek out. This was probably my first dip into the fashion world, but I still didn’t really know how to pay attention to trends.

The Lesson to Take to College:

Shopping vintage is an awesome way to update your closet without shelling out too much money, and since most trends are just repeats of old trends (like how the ’70s are coming back right now) you’ll still be in style.

Another great way to update your wardrobe is to mix and match your “nice” clothes with your lazy day clothes. Band tees look super-cute and spring-ready if you knot them in the front with a skirt and a pair of white sneakers.

Junior Year

Style Evolution Junior Year

Product Information: Dress, Sweater, Rings, Chain, Socks, Shoes, Backpack

Junior year was all about layers and proportions. I couldn’t just wear a dress, I had to layer a sweater over it and add on knee-high socks. My drawers began to overflow with crop tops. I hardly wore pants, and instead traded them in for skirts, dresses, rompers, and jumpsuits.

I also invested in a stylish pair of heeled booties that I wore all year long, and started wearing my signature chain (stolen from my mom, as always). I spent every long bus ride I had with my nose stuck in a fashion magazine, and I began to really pay attention to the emerging trends around me.

The Lesson to Take to College:

When you roll out of bed groggy for an early class, resist the urge to wear sweatpants! Stay fashionable with a simple dress, romper, or jumpsuit. They’re just one-piece, so you can throw them on and you don’t even have to worry about matching.

Double the wear of your dresses by layering other pieces with them– no one will know that “skirt” you’re wearing is actually the dress you wore last week. Also, a great pair of shoes that goes with everything you own is always a good investment. 

Senior Year

Style Evolution Senior Year

Product Information: Top, Skirt, Chain, Jacket, Shoes, Bag

Now, in my senior year, I like to think that I’m pretty on top of the latest trends. My style is more minimal than last year; I see the appeal in the simplicity of a dress without tons of layers and accessories.

My look is also more functional than it used to be; I’ve invested in a few key pieces for bad weather days, like cute yet functional waterproof booties, a beautiful fall jacket, and thick leggings. My drawers are still overflowing with crop tops, but I wear more pants than I used to, as well as some of my favorite trendier items, like matching tops and skirts.

The Lesson to Take to College:

Definitely invest in a few pieces that you’ll wear forever. Think about the fashion problems you often have, and get some functional solutions. Do you constantly find yourself getting cold? Maybe you need a heavier jacket. Do you wish you had a cute pair of shoes for those gross slushy days? Find cute waterproof boots.

If you like to stay on top of trends like I do, get pieces from cheaper places like Forever 21. That way, you didn’t waste a ton of money when the trend goes out of style next season.

What I’m Bringing to College

I’m not in college yet, so I can’t tell you where my personal style will end up, but here are some important pieces that I plan to bring:

  1. Basics. Of course, I plan to bring some basic clothing items that always come in handy, like my trusty freshman year v-necks, tanks, and leggings.
  2. Versatile pieces. Like I mentioned, clothing items that go with everything are a great investment. I love my high-waisted jeans and the dresses that I wear all the time.
  3. Trendy items. Since I’m studying fashion, it’s important to me to keep up-to-date with the latest trends. In addition to the basics, I plan to bring along my drawers of Forever 21 crop tops and whatever else is trendy when I leave. 
  4. Weather-appropriate clothes. Many of you will probably be going to schools with different climates than the ones you’re used to. Since I’ll be in New York, I want to be extra prepared for the cold winters and for walking in the rain, so I plan to bring my heavy winter coat and my favorite waterproof booties.

What do you think?

What’s your most cringe-worthy high school outfit? How has your personal style evolved over the years? What’s the most important clothing item you took/plan to take to college? Let me know in the comments!

5 thoughts on “The Evolution of My High School Style”

  1. Brilliant. I had a very similar timeline. I remember when high rise jeans showed up, and then two years after that, I threw away all of my lower rise anything. I have to admit that I am still a jeans and t shirt type, and still love high rise skinnies, although i now lean more to mom jeans or higher rise Levi 501’s (thrifted). I really don’t mind when people wear sweat pants, or really anything, as long as they get the proportions right, and stick to better made pieces. I love subtle crop tops with a nice pair of high rise joggers, as long as its all of a nice, heavy cotton, not some cheap rayon blend or something.

  2. Your outfits are really well put! I remember being well dressed in freshman years, but it all went downhill during my senior year. I went from dresses to skinny jeans and cheesy boyfriend hoodie like

  3. my worst outfit was when I was in my weird mall goth phase in 9th grade and wore a circle skirt with buckles, black tights, knee high striped socks, and an old hoodie with band patches…ouch. after that, my style evolved to a more feminine style, but I still always wore eye catching/trendy item that weren’t very practical or functional for every day (think of either club dresses or fancy rompers). Now, my style is more relaxed. I wear whatever is comfortable, chic, and easy to throw on. I pay attention more to the material and fit of the clothing..I look out for scuba knit material, spandex blends. rayon, etc.

  4. You were a very well dressed high school student. When I was in high school, I wore denim Abercrombie skirts every. single. day. for at least two years.

  5. to be honest i loved all the outfits thay you posted here, even the freshman year one! my wardrobe evolution, i think, is mainly my discovery of tailored pieces/things that fit me better. i’m a bit on the petite side, so for me oversized clothes only serve to make me look like i’m drowning in fabric instead of effortless, haha. like you, i also think i’m more drawn to girlier pieces now that i’m a junior.


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