STYLE EVOLUTION: What I Wore in High School 1999-2003

I know it’s late April when I start seeing the sidewalks of Charleston and Huntington covered in pastel-colored ball gowns and too big tuxedos.

Then, I start thinking back to my prom, and then I start thinking about high school, and then I remember that this year is my 10 year high school reunion. Yikes.

I thought it would be interesting to post a little bit about who my fashion icons were at the time, and what I wore:

Liz Parker from the TV show Roswell | Joey Potter from the TV show Dawson’s Creek | Jackie O
Ali MacGraw from the movie Love Story | Everything from the movie Blue Crush

If I were to really describe my fashion sense during high school, I’d describe it as a preppy surfer girl, which more or less equals out to Abercrombie & Fitch, during its heyday. I liked simple clothes that were easy to wear, which I still do. I was also very much into vintage clothing, especially flares from the 1970s. I’m one of six kids, and at the time there were a couple of kids in college and some of us still in prep school so money was pretty tight. I couldn’t afford the Abercrombie that everyone else was wearing so when I was stuck shopping at Goodwill for clothes, I decided to really go ahead and embrace vintage.

My mom was another one of my inspirations. My mom grew up in San Fransisco during the 1950s and 1960s. Yes, she hung out at Haight-Ashbury during the Summer of Love. I loved going through the few pictures she had from those times and getting a sense of the styles that people were wearing and then trying to recreate them from the racks at Goodwill. I found the best vintage shop in Huntington around that time, it was just a little hole-in-the-wall by where the Village on Sixth is now located. I had no trouble finding the flares I loved so much there. I got all sorts of jeans, sweaters, and amazing tee shirts from there. It also sold the finest in head shop paraphernalia.

However, there was one little thing to keep in mind about my high school years. I wore a uniform from the age of 6 to the age of 18.

This is based off my senior year. I had to wear khakis or navy blue pants or skirts. We had polo shirts with the school logo on them that came in white or navy, and on cooler days we could wear a plain navy sweatshirt/sweater. My accessories included Wallabee shoes because they are the most comfortable shoe on earth, a yin yang necklace because that was the thing at the time, and I had a giant tote bag that I used instead of a backpack.

Here’s what I wore on the weekends:

Flares, camp shirts, and chunky turtlenecks were favorites of mine. For a few years I incorporated a hint of military into my closet because I found some old Army shirts at Goodwill and loved them. There’s the obligatory surfer-inspired gear all high school girls wear at one point. I had a crazy collection of messenger bags during high school, I still love them today. For shoes I typically wore my Wallabees from my school uniform, and the original Candie’s slides. This was back when they were $50 and sold at Nordstrom instead of Kohl’s.

I won’t lie, I would still wear 70% of the clothes I owned in high school.

Here’s one of my senior portraits:

Sweater? Check. Low-rise flares? Check and check. Converse? Check, check, and check.