Welcome back to *Cash Register Alert*, the newsletter about all things ‘90s and ‘00s nostalgia, named after the best sound on AOL Instant Messenger. It’s been a minute, but we are back with a fresh issue — and this time, we’re getting into the good, the bad, and the ugly of late ‘90s-early ‘00s fashion. And if you haven’t yet subscribed (it’s free!), hit the button below so you don’t miss a single trip down the ‘90s and ‘00s rabbit hole.
Okay, okay, it’s been a bit more than a minute. The last time I popped up in your inbox, it was Spooky Szn and we were talking all things Ouija Board. Now it’s the cold dead of winter, so clearly we’ve had a ~Time Jump~ here. But, to be fair, I have a pretty good excuse: I’ve been working on my first novel, which also happens to take place in the ‘90s, so it’s safe to say that my brain has perpetually been in 1999 — more than usual, even.
One particular thing I’ve been thinking about a lot while writing is late ‘90s fashion. The amount of times I’ve consulted back issues of dELiA*s catalogs (thanks to this glorious Tumblr) are endless, and I’ve googled “1999 men’s fashion” more than I can count.
To be sure, a lot of ‘90s and early aughts trends have made a comeback in the past few years: choker necklaces, cropped shirts, spaghetti strap dresses worn over Ts — the list goes on. (Hopefully we can all agree to keep low-rise jeans in the dusty history books, but I already see certain celebs who will not be named trying to revise that one. We can’t let it happen! We must take a stand!)
But there were also plenty of trends that I cannot imagine giving a healthy revival outside of themed parties...for one, those jeans without the back pockets? Why?
Women’s clothing already has fewer pockets than men’s (which is BS! I’d argue we need more pockets for all our stuff!) and then we really decided it would be okay to get rid of the back ones too? Quick question — if you were Alanis Morissette, where TF would you put your hands? Also, speaking of hands, wasn’t that the era of sliding your hand into bae’s back pocket when you strolled through the mall on a Friday night? I suppose when you think about it that way, it was a good deterrent if you didn’t want someone’s hand in your back pocket, but an-y-way I digress.
Another confusing trend I cannot wrap my mind around (and shoutout to my friend Kendra for reminding me of this one) is wearing SKIRTS over JEANS. Why did we do this to ourselves? Who told us it was a good idea? I feel like Marissa on The O.C. definitely wore this combo at a Bait Shop concert and then we were all like, “Oh that is fun, I will obviously look just like her if I dress like this.” But it was certainly A Thing that celebs did IRL too, probably on the glossy pages of Teen People.
Something else I’ve been thinking about is the fact that this was all pre-internet as we know it today — and pre-social media. We weren’t inundated by the algorithm feeding us pictures of whatever the ‘90s equivalent of the Nap Dress would have been, nor did we have immediate access to what celebs were wearing on any given day. Influencers weren’t even really a thing; sure, there were the cool LiveJournal accounts (long live Hot Fashion), but there wasn’t exactly a cohesive effort to get you to buy a $500 dress covered in strawberries.
To that end, I’d argue that we were the influencers for each other — in the sense that we saw what our friends (or the popular kids) were wearing at school, and then decided we should probably dress that way, too. That maybe if we wore the same shirt and carried the same bag as the coolest girl in class, we’d somehow be a little cooler ourselves.
Catalog Photo: deliascatalogs.tumblr.com
As it does now, fashion carried a significance that went beyond what we were literally wearing. Remember the feeling of putting away your new clothes after going back-to-school shopping and thinking of all the ways you were going to be ~*different*~ this year, just because you bought a couple new shirts at PacSun?
I asked a few friends if they had a go-to outfit that made them feel cool — AKA the ensemble they’d put on if they had to give a presentation in class, or they knew they’d see their crush the next day. We all had that outfit, right? Here’s what a few of them had to say:
“Bell bottoms and collared chenille babydoll tees from The Limited. I owned a million colors.” —Roberta
“In 2003, it was black lycra flare foldover pants with a pink rhinestone cap-sleeved Bebe top.” —Jen
“Anything with Chucks!” —Camille
“If I wore a navy t-shirt with a grey t-shirt over it and rolled the sleeves up, then paired it with blue jeans and fresh white Air Force Ones, I felt unstoppable.” —Mike
“Prob these exact jeans lol. I often tried to replicate Buffy’s outfits.” —Alicia (referring to the dreaded no-back-pocket jeans, ahhhh!)
Looking back now, the clothes are certainly a signifier of the time, but there’s also the feelings that went along with them. I don’t so much remember the wide-leg JNCOs as much as I remember wearing them because my best friend did, and I wanted to feel effortlessly cool like her. The outfits — the flared jeans, the choker necklaces, the Chucks — they were part of the set dressing for our formative years, the way we presented to ourselves to the world as we figured out our place inside it.
And it makes sense, because ‘90s nostalgia as a whole isn’t really about the material things; it’s about conjuring the emotions that can’t be felt in the exact same way again: the feeling of getting ready for a middle school dance; flipping through the yearbook to see what your crush wrote to you; turning on the radio at the exact time your favorite song comes on; laughing until your sides hurt at a sleepover with your best friends.
This is getting a little more ~philosophical~ than I intended (and maybe than you all anticipated!) but I also think it’s worth acknowledging that nostalgia feels especially good right now, during one of the most uncertain eras of our lives. So many of my friends are making playlists of the bands they listened to growing up, or are re-watching movies they loved during childhood. Returning to something known, something familiar, during a time that’s anything but that — well, that’s a better form of self-care than a bath bomb IMO.
So if nostalgia feels good, if dressing like your ~old self~ feels comforting, lean into it. Bust out those choker necklaces, the mood rings, the striped t-shirts. Just as long as we can all agree to leave those weird no-pocket jeans where they belong: frozen in time, next to Britney and Justin in all-denim, cans of Surge, and triangle-folded love letters we passed to each other in the halls.
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