Favourite Outfits of My Teen Years

It’s no secret I love clothes and fashion, and I always have. Every day is an opportunity to play dress-up, in my opinion, or at least to wear something pretty. Some of you may remember when I Kondo’d my house (and life), I discovered something important about myself: clothing sparks joy for me. I love my entire wardrobe; I love every last one of my twenty-plus black sweaters, my dozens of black tops, my twelve black bikinis, and my two shelves full of tightly rolled up yoga clothing, in varying hues. My friend Lyndsey (HI LYNDSEY) is a professional organizer, and I’m pretty sure she would faint if she saw my stuffed-to-the-brim closet. BUT I LOVE AND WEAR THEM ALL, LYNDSEY.

I’m at the point in my life where I am very comfortable with my own sense of style. True, I do like to keep up with current fashions, but I don’t feel the need to adopt them unconditionally. For example, I’m not a person who is flattered by peasant blouses or white jeans, and I’m literally too cold to wear the cold shoulder look. I’ve already done my time in pleated shorts and cut-off jeans, and so I shall leave the youth fashion to the youth for whom it is intended.

And yet, it is very fun to look back at the fashion I adopted when I myself was a youth. Last week, my friend Swistle (HI SWISTLE) wrote about favourite outfits in high school, and I have been thinking about it almost non-stop since then. I’ve been riding a wave of nostalgia for the late 80s/ early 90s, and the accompanying terrible fashions. I was at my parents’ place on the weekend and I thumbed quickly through a few photo albums. HOO BOY. Those were the days, my friends.

My own personal style really changed a lot from junior high to senior high, and it also changed a lot from year to year. I feel that the summers were a time of renewal and reflection about our own personal fashion, and that September was a time of new beginnings, clothing-wise. It was the time where we all decided what we wanted our look to be, for better or worse.

Grade Seven, 1987-88

My very favourite outfit was one that I have photographic evidence of, since I wore it on the first day of school. It was a long, full skirt that was meant to look like denim but was actually cotton. I paired it with knockoff white Keds, a white tank top, and a blue-and-white striped blouse that I tied in front.

I also had a denim slouch bag! And, if you look closely, light-blue nylons. I wore a lot of skirts in the beginning of grade seven; notably a light-blue bubble skirt, a beige ruffled skirt that I paired with an enormous white t-shirt, tucked in, and a pale pink skirt that I wore with a pale pink sweater and pale pink ankle boots. I was a sight in pastel, apparently. I wore skirts until I figured out that junior high boys were terrible and that they always tried to look up skirts when walking up the stairs, or flip them up when you were innocently standing at your locker.

Grade Eight – 1988-89

Once I figured out the terrible truth, I lived in jeans and gigantic sweaters. I had a few cable-knit sweaters that I begged for – and received – at Christmas. They were ENORMOUS. I wore acid-wash and other light-wash jeans, Levi’s with the red tab, rolled up at the ankles. Nothing is so terribly unflattering as baggy, high-waist jeans rolled at the ankles with a gigantically baggy, tucked-in t-shirt. But such was the fashion back then. I found this gem at my parents’ house and it cracks me up uncontrollably.

Ah, nothing says excitement like being fourteen years old and getting your photo taken for the no-cavity club at the dentist. Just look at the size of the t-shirt, with polka dots, no less. Look at the knockoff Swatch watch. LOOK AT MY HAIR.

A store had just recently opened up, in the spring of 1989, a store that was, to me, life-changing. It was called Freedom, and it sold many items like jeans and t-shirts embellished with peace signs. Oh, how I loved that store.

Grade Nine – 1989-90

Grade Nine was my year of predominantly black sweaters – a trend I have kept for a lifetime since – a ton of jewelry – ditto – and ripped jeans or long, multicoloured broom skirts. I also embraced band t-shirts from long-since-unbanded-and-usually-dead musical acts, such as The Doors.

Another dentist photo! I guess I’ve always been good at brushing my teeth. It is very hard to tell in this photo, but I have – in addition to a LOT of necklaces and my dad’s old watch, a long fake-silk scarf used as a belt in my jeans. My jeans would have, of course, been Levi’s 501s, and they would have been frayed at the bottom and, rather than rolled, pinned tightly at the ankles.

Grade Ten – 1990-91

Grade Ten was the year I fully embraced the dichotomous look of either ripped jeans or dresses. There was no in-between. I loved babydoll dresses, particularly crushed velvet ones, worn with tights, army-style boots, and a trench coat. It was the look of the early nineties, along with long, permed hair. Sadly, I have no photographic evidence of this in my possession, but I do have this lovely one with a classic Sulky Teen look.

Long, silver chains with crosses were my jam, along with silver hoop earrings and a mood ring. My mood ring was stuck on black, however, because even then I had terrible circulation and my hands and feet were always freezing. In fact, I remember a boyfriend I had around age 16, who looked at my bare feet and asked, alarmed, how I bruised them so completely. They were just purple from my lack of circulation, and were totally normal for me.

Grade Eleven – 1991-92

My very favourite outfit I remember so well, but I cannot find a photo of it. I wore it on my first day at my new high school, and it was red plaid HOT PANTS paired with thick black tights, a black mock turtleneck, and a black blazer. I also wore black loafers. God, I loved that outfit. Jeans, loafers, and blazers were very stylish at my school at the time, and I wore them all the time. Jeans were, thankfully, no longer pinned or rolled, but they were high-waisted and straight-legged, and t-shirts were oversized and tucked in. I found this treasure from my high school Europe trip, in which I’m wearing one of my favourite outfits, complete with Revlon’s Love That Red lipstick.

Also from that trip: my beloved leather bomber jacket, which I bought in a Florence market, paired with pink striped shorts and gladiator sandals.

Vogueing was popular back then.

I also had this outfit, which I absolutely loved and I would still probably wear today, mutton dressed as lamb be damned. I bought it at Le Chateau, and it was a short black skirt embellished with fabric daisies, and a swingy matching top. Oh, how I loved it. Note also my exclusive use of Love That Red.

Grade Twelve – 1992-93

Sadly, I cannot find ANY of my casual photos from grade twelve. I’m sure there are some in existence, but I cannot locate them at this time. Suffice it to say that by Grade Twelve, I had gone full-on Princess in my clothing choices. Kilts and turtleneck sweaters were my signature look, with my long, hot-rollered hair and Love That Red lipstick. I also seemed to have a lot of coloured jeans – high waisted and belted, naturally – and silk blouses. SILK BLOUSES, PEOPLE. It goes without saying that those blouses were also ridiculously oversized, as was everything back then. Although I don’t have any photos of these terrific outfits, I do have one on my graduation day of my hot-rollered hair:

That took SOME effort, let me tell you.

So now it is your turn – what were your favourite outfits in your teen years? Were your favourite clothes a sign of the times?

Small side note: I just realized that the song, Sign of the Times, is by Harry Styles. Guys, I like something by Harry Styles! I’m a modern girl! Proof positive that my husband is WRONG when he says I’m stuck in the past, in terms of music. Although it is true that my favourite genres are Motown, 70s soft rock, and “Fat” Elvis. Is that a genre? I don’t really know, but Kentucky Rain is my jam. xoxo