First Day of School Outfits: Our Highlights and Lowlights

Posted: Friday, August 30th, 2013


The first day of school—it’s the one day when kids truly dress to impress. Savor it and take pictures, because grass-stained pants and woefully mismatched colors will soon rule the day.

First day of school outfits can make or break an entire school year, something the staff knows all too well. Check out a few stories of the highlights and lowlights (mostly lowlights) of first-day fashion from the team.

Blythe and her older brother, in 1992, walk to the first day of school together.

1995: Blythe and her older brother Trent walk to the first day of school together.

Expires in One Year
It took exactly one year for my first day of school outfits to go from the best dressed list to the worst. For my first day of second grade, at my new school, I wore a sweet burgundy Laura Ashley dress with puff sleeves and pink flowers. I was the epitome of ’90s chic.

For the first day of third grade, I wore an outfit that I had bought especially for the occasion: purple cotton shorts, white athletic shoes, and a teal T-shirt featuring a picture of Esmeralda from The Hunchback of Notre Dame. I think at the time, I thought it made me look like Esmeralda. –Blythe

Yo Quiero Smaller Shirt
The only first day of school outfit I have any recollection of is the one I wore on my first day of seventh grade, and only because it involves the Taco Bell Chihuahua.

In the late ’90s, Taco Bell made a string of TV commercials starring a talking Chihuahua. This dog had become enough of a part of the cultural landscape by my seventh grade year that they were selling T-shirts with the Chihuahua’s likeness on it at my local Mervyn’s. I made my mom buy me one. I don’t know why.

It was bad enough that I wore a T-shirt with the Taco Bell Chihuahua on it to my first day of seventh grade, but it was from the men’s department, so it was about two sizes too big. But I didn’t stop there: I wore it with a pair of jeans that were embroidered with two big butterflies on one thigh, because nothing says femininity like a T-shirt that fits you like a pillowcase. I believe my purple bucket hat was also involved, and since this was 1998, I’m going to bet my platform Skechers rounded out the ensemble.

Long story short, I’m really glad my parents had tired of taking first day of school pictures of me by then. –Jody

On the first day of seventh grade, I wore skorts. I regret my decision ever since. The only reason I wore them was because all of sixth grade, I wore long pants and I wanted to wear a skirt on the first day of class. –Andrea

The No-Regrets Outfit
So this was a first-day outfit to end all first-day outfits, and trust, I’ve had some good ones over the years. For my first day of third grade, I wore a black and white houndstooth suit (i.e. matching trousers and jacket) and wore a sunshine yellow shirt underneath. I wore a matching sunshine yellow headband, and matching sunshine yellow socks, too. And then, of course, classic white Keds on my feet. I would totally wear that exact same outfit today. –Carlee

Beware the Flimsy Sandwich
My outfit earned me a nickname on my first day of seventh grade: “Foods Levine.” There wasn’t anything inherently wrong with what I was wearing at the time; it’s just that a flimsy cafeteria sandwich managed to disassemble itself all over the front of my new polo shirt—mustard, mayonnaise, tomato and all. A foreign exchange student who witnessed this gave me the nickname because of the “great many foods” that seemed to have found their way onto my shirt.

He ended up nicknaming another kid “Crouton,” because this guy would bring literal bags of croutons from home and eat them for lunch. By day’s end, he’d be covered in crumbs. I still maintained the dubious honor of being called Foods because, as my foreign exchange friend put it, “Crouton just has crumbs. But Levine, your shirt had so many food kinds!” –Mack

Gems From the Closet
In high school I used to borrow a lot of things from my dad and older cousin’s closets. I remember one Back to School outfit with a pair of jeans, a button up Oxford, a really wide tie, a suit vest, and a fedora. I also lived through the Michael Jackson era, so there were a lot of us in first grade running around in pleather zipper pants. My only comfort is that I never wore the single glove that went with it. –Danielle

Kindergarten, Day 1. I wore a dress. White cotton, trimmed with lace and soft pink floral print. It was my favorite dress at the time. In fact I think I wore it at Christmas, too. So, in my favorite, “fancy” pink and white dress, I had a great time digging in the sand, crawling through play equipment, sitting on the rug and listening to my teacher.

But the star of my first-day-of-school outfit (and when I say outfit I mean “gear”) was my lunch box. Square and plastic and orange, emblazoned with my favorite character, it was the pièce de résistance. I’d picked it out for myself. There for all the world to see was my hero: Mr. T.  I watched both of the cartoons he was in. I loved the The A-Team; it was one of the only things I could watch with my brother where he didn’t ruin it rooting for the bad guys.

As I looked around at my classmates it hit me: Every single girl’s lunch box was pink or purple, maybe red. None of their lunch boxes resembled mine at all. And all the boys had G.I. Joe, monster trucks and “boy” cartoons, in colors more like my lunch box. I was flooded with self-consciousness. No one said anything to me that I can remember, or looked at me askance. I tried with my small hands to cup both sides of my thermos, which was covered all the way around with Mr. T’s likeness, so that no one could see what was on it and make fun of me.

I didn’t say anything to my mom about it, and I don’t remember what became of that lunch box. I wish I still had it. I do know that sometime afterward I picked a purple, less gender-charged Fraggle Rock lunch box and disliked it so much that I stuffed it in a kitchen cabinet. –Candice

It Was a Sign
On the first day of my junior year of high school, I decided to rock these unbelievably atrocious vintage ’70s square-toed ankle boots. They were one size too small, and as a result I was forced to shuffle from class to class with an awkward gait that my friends found deliriously funny. I convinced myself that the pain was worth it. However, by lunchtime my feet were killing me.

Looking back, it’s almost as if my feet were crying out it vain, trying to tell me what a horrible fashion blunder I was committing by trapping them in these monstrosities. When I finally removed the hideous things I was writhing in pain because of the giant blisters that had blossomed all over my feet. Needless to say, I never wore those boots again. –Katherine

Walking Advertisement
I wore a T-shirt with the logo for Zildjian, a company that makes cymbals, on the first day of eighth grade. I wanted people to know I played drums. My tastes have since changed. When I see someone wearing something like that, I think, “He better be getting paid to wear that.” –David

Never Out of Style
Heading into sixth grade, I had no grasp on the concept of looking cool. I knew the fashion basics: dresses were pretty and tights were invented to punish little girls who allowed themselves to be dressed by their mothers. But, the more sophisticated clothing design releases of 1994, such as the revival of bell-bottoms and the low-slung backpack, escaped my purview. So, when the first day of middle school rolled around and I donned a pair of green jeans, a button-down white shirt, and paisley vest, I was completely unaware.

At lunch I approached a large table of girls, all of whom had their attention tuned to one unifying force: a girl I knew by name only. She seemed fine, but what I was to learn in the days ahead was that she had all the fixings of a cool girl—satin scrunchies, No Fear T-shirts, and a little baggie full of different flavored Lip Smackers.

She called out to me, “Hey Hanna, when’s the flood coming?” I looked down and noticed my beloved green jeans ended a full inch before my socks. The concept of cool and uncool struck me like a rubber slammer on a stack of Pogs. At that moment, I had just one choice. “You guys didn’t hear about that? Yeah, the Springfield Dam is about to blow!” Hilarious, but it worked. They laughed, and it upset the balance between cool and uncool enough for me to hang out and become BFFs. I learned an important lesson that day: funny is cool, and it never goes out of style. –Johanna

What was your most memorable first day of school outfit?

2 Responses to “First Day of School Outfits: Our Highlights and Lowlights”

  1. Cynthia James Says:

    Thank you. Just what I needed.

  2. Anonymous Says:

    I agree that wear what you want.

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