Why Real 90s Fashion Still Feels So Good

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There’s something radically freeing about looking back at old photos and realizing how much fun we had—even when our bangs were growing out or our sandals were a knockoff rather than designer. I remember, like Jenna, going to concerts in slightly-too-big striped shirts, grass-stained Bermuda shorts, and yes, Payless “Doc” sandals. I had a Lisa Frank notebook in one hand and a half-shiny, half-chipped mocha lip gloss in the other. Looking back, I see so much confidence—even through the braces and bad haircuts.

Here’s how you can bring that real late-90s magic into your own closet—awkward, brave, and beautiful.

Stripes: The Ubiquitous 90s Pattern

Jenna nails it: stripes were everywhere. Shorts, shirts, sweaters, and even sandals. The more colorful or wide-striped, the better. My own closet was filled with rainbow and navy stripe tees, a Union Bay sweater almost identical to Jenna’s, and random secondhand finds covered in every stripe variation you could imagine.

  • Styling tip: Try oversized striped tees with cargo shorts or denim Bermuda shorts (extra points if the shirt is a little too big).
  • Layering: Wear your striped shirt under a flannel or starter jacket for the ultimate throwback.
  • Fabric note: Most of my old striped shirts were cotton blends—easy to wash, soft, and forgiving (important when you’re living on after-school snacks).

Check out some trending 90s-inspired basics for modern takes on this classic.

The Glory of Bermuda Shorts and Chunky Sandals

Let’s talk about those infamous long denim shorts. Bermuda shorts were basically the uniform for anyone who didn’t want to deal with skirts or bike shorts every day. Loose fits, frayed edges, and a mid-thigh to knee length that suited everyone, regardless of body shape.

Pair these with Payless “Doc” knockoffs or platform sandals—ideally worn with socks if you want full-on authenticity. My first pair of chunky sandals weren’t real Doc Martens, but I loved them just the same. And yes, socks and sandals is one of those divisive 90s moves that’s come full circle (and is oddly comforting).

Style tips for today:

  • Don’t be afraid to size up in Bermuda shorts for the slouchy look.
  • Platform sandals with or without socks—go with your comfort zone!
  • Sports or trending collections often have updated versions if you’re ready for a fresh take.

Starter Jackets and Statement Outerwear

A true 90s time capsule wouldn’t be complete without the windbreaker or Starter jacket. Bold team logos, slightly too-big fit, loud color blocking—these jackets were worn over everything. Clip-on Beanie Babies or enamel pins added even more personality. My favorite was a blue and white Yankees Starter jacket, its zipper always jingling with some Happy Meal freebie.

Iconic 90s Accessories: Beanie Babies, Hemp Necklaces, and More

Beanie Babies as zipper pulls. Clay bead hemp chokers. Angel pendants and slap bracelets. These weren’t just accessories—they were a rite of passage. I still have my first hemp necklace, beads worn smooth by days at summer camp.

For some real 90s flavor, layer your necklaces, mix in charity wristbands or handmade friendship bracelets, and reach for that tinted lip balm or (yes) mocha lip gloss.

  • Style hack: Don’t be afraid to stack accessories. Eclectic and “too much” is pure 90s.
  • Mother/grandmother collections are a goldmine for vintage finds.

Baby Tees, Cloud Backdrops, and Embracing the Awkward

Who can forget the iconic baby tee? Slightly cropped, fitted, and emblazoned with cartoon angels, brand names, or cheeky slogans. That, plus a pair of jeans and a cloud backdrop (extra points if you had braces or butterfly clips in your hair)—and you’re straight out of a 90s yearbook.

Personal tip: If you want a nod to this look now, pair a fitted baby tee with high-waist jeans and go for minimal makeup with a swipe of tinted gloss.

Inspired by TV, music, and pop culture? Explore all things 90s here.

Conclusion: Say Yes to Real 90s Fashion—Awkwardness and All

So, what makes real 90s fashion so special? It’s the honesty. The homemade vibe. The permission to be imperfect—a time when comfort, color, and self-expression mattered more than “rules.” My advice: Don’t wait for the perfect “aesthetic.” Wear the stripes, clip that Beanie Baby to your zipper, layer on the weird jewelry, and embrace a little awkwardness. After all, that’s what growing up—and great style—is all about.

Need some inspiration to start your 90s comeback? Check out more authentic, trending, and pop culture-approved pieces here. You might just fall back in love with your inner 90s kid.

@jennaabarclay The late ‘90s were all about stripes and starter jackets for me (and mocha lipgloss) #90s #90sfashion #90saesthetic #y2kfashion ♬ original sound – Jenna Barclay

The late ‘90s were all about stripes and starter jackets for me (and mocha lipgloss) #90s #90sfashion #90saesthetic #y2kfashion

“The 90s nostalgia trends are so cute,
but let’s look at some real 90s fashion
because not everything was that cute.
Let’s just for a second,
ignore the growing out perm that I have going on here
and talk about this outfit.
First of all, everything was striped in the late 90s.
Everything, like 95% of my clothes had some form of stripe.
Even my sandals.
And what are these over. What are these,
like, denim Bermuda shorts?
Here I am at the Backstreet Boys Millennium concert,
1999, with growing out bangs, glasses,
braces, mocha lip gloss, and an Lei T-shirt.
Another glimpse at this outfit.
So you can see that I am in fact
wearing the payless knockoff version
of those DOC Marten chunky sandals
with socks. With this outfit.
This is actually kinda cute.
This is probably like 1995,
maybe 1996.
I’m pretty sure this shirt had some sort of, like, genie lamp on it.
It is definitely too big for me.
The bangs are not really good,
but, you know, kinda cute.
Definitely very 90s.
I’m kinda rocking that haircut, though,
I’m not gonna lie.
You really wanna bring back the 90s,
get a starter jacket
and clip a McDonald’s Happy Meal Beanie Baby on the zipper.
What is this?
This Union Bay sweater with the neon green stripe on the arm.
This is like the most 1997 thing that’s ever 1997.
And here we have my school picture from I think, sixth grade.
The Baby T This is Angel on the cloud background. And, oh,
my god, this necklace,
these hemp necklaces with these little clay beads.
Oh, my god,
this is the real nineties.”