A Look Back At The Good, The Bad And The Ugly -- The First Day Of School Outfit

The planning of these outfits was critical in this young girl’s life.

It’s back to school time ― even if you don’t have kids surely you know this based on a few things:

  • The back to school aisle has been up at Target since 4th of July.

  • End cap placement in grocery store of juice boxes.

  • Bombardment of “First Day!” photos in your Facebook feed.

Growing up I was always so excited for the first day of school – I planned for it like a bride in preparation of her big day.

I loved getting new things to start the school year off right: a new Trapper Keeper, a big three-ring denim binder, new pee-chee folders, the perfect lunch box and most importantly ― new clothes.

I loved art and reading, I wasn’t so interested in science or math. I was also interested in knee socks, barrettes and shiny brand new Mary-Jane’s.

A few first day of school outfits are permanently burned into my memory. I can still smell the leather of the shoes and feel the way the brass button slipped into the clasp on my jumper.

Painstakingly laid out in the shape of a dead body on the pink carpet of my childhood bedroom on first-day-of-school-eve, the planning of these outfits was critical in this young girl’s life.


Holy hell, every little girl had a little sailor dress in 1976. I felt very sassy in this number. But what I remember the most about this day was the shoes. Brand new from Buster Brown, navy and mud brown sturdy-as-hell little lace up shoes. A precursor to my ‘90s obsession with Doc Martens.



This outfit ruled! I had dreams about buying it and then after I got it I counted down the days on a calendar until I got to put it on. Why? THE SHIRT HAD MATCHING KNEE SOCKS.



Oh look, I am mature now. White blouse with puffy sleeves, one of those tiered prairie skirts in a lovely shade of pink, cute open toed sandals and... socks. Crayola book bag. And my cat Marshmallow who I tried to take on the bus.



Oh shit, this isn’t good. We had just moved to Florida from New York. My mom and I picked out this plaid monstrosity at Beall’s Department Store in Northdale Plaza. This is not cute. I remember being pretty excited about this outfit and thinking I looked really good. I also remember wearing pantyhose with Keds sneakers that day. In the Florida heat. Really not good.



Things are not improving. Mouth full of braces, way too much make up, cheap, white blouse with elephant-gray not flattering old lady skirt. PERFECT! I like how my parents thought “the gutter” was the perfect place to snap a first day pic. At least I didn’t have to wear a tie, like my brother. We are absolutely thrilled.



Here I go, car keys in hand, highly annoyed that my picture is being taken and dressed very business-like to go to high school. I’m all St. Elmo’s Fire-d out, too cool for school, ready to drive my big brown bitchin’ Camaro off into the sunset. A senior ― ready to rule the school. 

It’s a damn good thing there was no social media/Facebook back in the day. I would have posted outfit after outfit – annoying everyone with the endless possibilities that were available to create the perfect look.

The only upside would have been that someone could have possibly intervened and tried to talk me out of the pantyhose with Keds.

Lori’s website, Drawn to the ‘80s, is where her five year old drew the hit songs of the 1980’s. Her blog, Once Upon a Product, is where she writes about important things like beauty products, food and her Mick Jagger obsession.



First Day of School Pictures