14 Things We Thought Were Super Uncool In The '90s

It feels weird to me to think about all of the things we thought were uncool in the ‘90s — especially because so much of the stuff that we did think was cool back then now seems unbelievably lame. I mean, how on Earth could we have been so judgmental about someone wearing a backpack on both shoulders, when we all honestly believed that T-shirts with Looney Tunes characters in hip-hop clothing were the height of covetable fashion? How did we collectively decide that certain brands and styles were uncool, when random, ridiculous things like Crystal Pepsi, collecting Beanie Babies, giant Doc Marten sandals, and wearing your jeans backwards (à la Kris Kross) all managed to fall on the “cool” list? Friends, it was a weird time.

Making this list has reminded me of how arbitrary the lines between “cool” and “not cool” are. As an adolescent and teenager in the ‘90s, I worried constantly about avoiding things that were “uncool,” lest I be labeled as uncool myself. It seems preposterous now, but I suppose that’s just a marker of being young and insecure. I have a newfound respect for my parents, who must have found themselves struggling not to roll their eyes constantly as my sisters and I obsessed over labels and trends. Silly though it may have been, here are a few things that would have landed on our “not cool” list in the ‘90s:

1. Carrying your backpack on both shoulders.

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Back in the day, it was considered completely uncool to wear a backpack on both shoulders, regardless of how many textbooks you were lugging around. My mom would always see me struggling to schlep around my own weight in three-ring binders, and tell me to wear my backpack the way it was designed to be worn, but I steadfastly refused to use both shoulder straps, because that would be, like, so lame, Mom. I’m sure I’m not the only ‘90s kid who now has terrible posture. Blame the backpacks (and our own adolescent stubbornness).

2. Homemade lunches.

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One’s coolness in the cafeteria depended on how much prepackaged food you brought with you to lunch. If you had a pizza Lunchable, you were ruler of the school (never mind the fact that pizza Lunchables are objectively awful). If you had a yummy, healthy homemade sandwich with a sweet note from Mom? LOSER.

3. A cap facing front.

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Every ‘90s kid knew that baseball caps may only be worn backwards or to the side. Wearing one facing front — so that it could actually shield your face from the sun, ugh — meant that you would never, ever be as cool as Will Smith.

4. Skinny jeans.

In the ‘90s, pants were large and often pleated. Many a fly young woman owned light blue, tapered jeans that were always sort of puffy up top and tight at the ankles. It was way sexy. Dudes were usually either clad in pleated khakis or wide-legged jeans hung so low that they had to belt them around their thighs to keep them from falling off completely.

5. Things that were not name brand.

People in the ‘90s were obsessed with labels, and adolescents and teens were no exceptions. In my middle school, one of the coolest garments you could own was a CK1 t-shirt — not the actual perfume, mind you (because none of us could afford it), but just a t-shirt with the brand label printed on the front. When I think about it now, all I can say is, “Why? Why were a bunch of middle schoolers obsessed with a logo for an emo unisex perfume?”

Especially among adolescents, who are never the most practical when it comes to … anything, really, brands were a really big deal. In my middle school, having a generic version of something rather than the fancy label was considered completely uncool. I was outraged when my mom tried to get me the L.L. Bean version of Tevas instead of actual Tevas. A generic polo style shirt was awful if it didn’t have a Ralph Lauren or Tommy Hilfiger label. I think about that stuff now and amazed that my mother didn’t hate me and all other label-obsessed preteens. We must have been insufferable.

6. Nerds.

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Nerds are pretty mainstream now, and a lot of people use the word “nerd” as a term of affection and even pride (and, sure, some people still use it derogatorily, but it has a lot less venom attached to it than it once did). But, if ‘90s TV shows and movies are anything to go by, nerds were still firmly entrenched as social outcasts back in the day. Shows like Saved By the Bell and Family Matters, for example, featured nerd characters as essentially clowns, awkward idiots there purely for comic relief. (One awesome, early character whose nerdy qualities meant that she was smart and capable was the incomparable Willow Rosenberg.)

7. T-shirts with the sleeves unrolled.

For girls, the only acceptable way to wear a t-shirt in the ‘90s was to roll the sleeves (See the CK1 shirt, above). Girls who failed to comply were driven into the desert and left to fend for themselves.

8. Minivans and all other cars that were not SUVs.

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In the ‘90s, SUVs became the coolest cars on the road. This may be specific to wear I grew up (Texas), but teenagers’ dream cars were not Corvettes, Mustangs, or other fast sports cars. Instead, the most coveted rides were SUVs like the Explorer or Cher’s Jeep in Clueless (despite the fact that those early SUVs, as my dad ALWAYS liked to point out, had an unfortunate tendency to roll). And minivans? Absolutely nope.

9. Non-processed food.

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Now a lot of food brands are going out of their way to hop on the local-organic-fresh-healthy food train, by marketing products as organic, “all natural” (whatever that means), healthy, and unprocessed (even when they totally are). But back in the ‘90s, people loved packaged and processed foods, especially kids. A ‘90s child would take a pack of Gushers over real fruit, or a Lunchable over a fresh meal, any day of the week.

10. Girls who wear glasses, apparently.

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In She’s All That, the main thing that seems to be standing between Laney, the film’s heroine, and popularity is her pair of glasses. She takes them off, and — Wow! — this former troll looks like Rachael Leigh Cook. Who would have guessed?

11. The soothing sounds of adult contemporary.

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Musicians like Michael Bolton, Kenny G, and Céline Dion were certainly popular in the ‘90s, but cool? Not so much. That’s not to say that teens and adolescents didn’t listen to their music — my sisters and I spent the entire summer of 1996 listening to Dion’s Falling Into You album — but they weren’t the artists showing up on MTV. (Remember when MTV seemed like the arbiter of cool? And the channel actually played music? I feel old.)

12. Barney & Friends.

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If you were over the age of 8 in the ‘90s, you probably, like me, thought Barney was the absolute worst. My little sister (who was in the age bracket for the show) loved it, but I hated it with a fiery passion. It just seemed so lame compared to the kids’ shows I watched as a little kid in the ‘80s. She-Ra: Princess of Power! Jem ! Who cares about a bumbling, singing purple dinosaur when you could have a literal superhero with a magical flying horse or a rock star with magic earrings? I don’t get it.

13. Old tech.

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Technology changed quickly in the ‘90s, and the new gadget that was all the rage one day was seen as totally lame the next. For example, we all thought Zack’s giant cell phone in Saved By The Bell was so cool in the early ‘90s, but by the end of the decade, we all wanted Nokia phones (because you could change the cover, which at the time seemed AMAZING), and the old Zack phone was in the reject pile. The same the happened with tapes when they were replaced by CDs, and floppy discs when they were… also replaced by CDs. Even VHS — which seemed cool to me in 1991 — was on its way out by the time Y2K came around.

14. Unironic enthusiasm.

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I think this is less a ‘90s thing than a “disaffected teenager” thing. In the ‘90s, Daria was my role model, and honest enthusiasm was out — but, in all honesty, that’s probably true of anyone who’s 16, regardless of what era they happen to be living in. Of course, though the ‘90s didn’t invent teen angst, it certainly had some of the best angry, alienated music and characters of all time. Who wants to key up their Nirvana tapes and watch Reality Bites with me? If we add in the clothes from Empire Records, we’ll create an inescapable vortex of cool.

Images: Miramax Films; Giphy (11); Paramount Pictures