Close your eyes and remember a time before Twitter, when The O.C. was on the air, and when you thought all college dorms resembled Elle Woods’ sorority house. You might have had a Xanga blog or a Myspace page, and you definitely had an AIM screen name. Learn ahead how 2000s high school fashion were and how to rock it now.
Let’s go back to the 2000s, and those nostalgic years of middle school and high school.
Like everyone else’s teenage years, my sweet triumphs were peppered with plenty of awkward and silly moments.
There was the time that my date asked me to homecoming by having the waiter slip a message in a fortune cookie. I was stoked for two weeks until that same date dumped me the day before the dance.
During senior year, my English teacher was less than enthused about a school-wide book project my entire class was required to participate in. I forgot about it until the day it was due, so I spent my lunch hour quickly writing a poem to turn in – and later won $1,500 in that very contest.
And I never scored or placed in any of my cross country races – but dang, the initiation sleepover was always a freakin’ blast.
However, one of my favorite things about taking this trip down memory lane is the ’90s and ‘2000s fashion.
Whether you just finished high school or you graduated several years ago, we can all relate to cringe-worthy wardrobe moments of our past.
Below, I’ve listed twenty items you were sure to have in your closet and a few reasons why I loved them.
After you finish reading, be sure to leave us a comment and tell us what closet staples you miss from your high school years as well.
Table of Contents
1. Distressed Flared Jeans
Product Information (From the left):
2000s high school fashion before there were skinny jeans before it was socially acceptable (and chic) to rock baggy, cuffed boyfriend jeans with a sassy pair of heels, man-made flared jeans, and the world was happy.
Plus, Kristin and LC on Laguna Beach wore them, which pretty much made them the coolest things ever.
Not just any old pair of flared jeans made the cut, though.
The perfect pair of high school jeans included strategic fading, manufactured (therefore, uniform and regulated) scuffs and distressed patches, and – of course – the signature back pocket embroidery, boldly announcing to the world exactly which brand your snazzy pants originated from.
Back then, I personally had a penchant for American Eagle jeans, and, well, I still sort of do.
Of course, these bad boys came with a price.
The number of detentions I was assigned as a result of wearing “holey” denim is completely astounding and borderline comical.
Ladies, let’s have an honest chat: growing up, my curfew was 11:45 sharp and my favorite extracurricular activity was show choir. I drank half of a beer freshman year of high school and felt so guilty about it that I tattled on myself the very next day.
Yes, being a badass wasn’t my forte, so instead of doing anything actually crazy (like skipping school or sneaking out), I rebelled in much more subtle ways – you know, like wearing ripped jeans to school, playing the snake game on my Nokia during class, and being tardy for an average of one class per day.
You know you’re doing something awesomely wrong (or terribly right!) when you set the school’s record number of misdemeanor detentions accumulated within one semester.
2. Birkenstock Boston Slip-Ons
About the same time that the first Now! CD was released, and there was one other thing I was in hot pursuit of – a soft suede pair of slip-on Birkenstocks.
They peeked out perfectly from under a (#1) pair of distressed flared jeans, and all of the coolest girls in middle school wore them with bright, patterned toe socks.
Of course, my parents weren’t exactly on board with getting me a pair of name-brand shoes which were sure to be ruined the first time I wore them on a rainy day or across a muddy patch of grass. Instead, I got the off-brand version, which my dad deemed “the Fakenstocks.”
Nowadays, I think I’d rather go barefoot than be seen in a pair of flat slip-on clogs whose body design was surely the inspiration for Crocs. People were rocking this during 2000s high school fashion.
But still, for a glimmering two years in middle school, my Fakenstocks traveled with me to eighth-grade football games, All American Rejects concerts, laser tag games, and countless group hangouts at the local movie theater.
Rest in peace, my dearly beloved mud-colored and clunky old friends.
3. North Face Fanny Packs
This happened well into the ’00s, not in ’93. Every single outdoor specialty shop in 2004 was suddenly inundated with young teen girls clamoring for a North Face…wait for it…fanny pack!
Of course, these fanny packs were not your mother’s fanny packs. Rather than being worn around the waist tourist-style, these puppies were made to be worn across your shoulders (like a bow and arrow quill) and made to function as a purse.
The anthropological side of your brain might find itself wondering, “What did a 15-year-old in the mid ‘aughts’ carry in her purse?”
Well, I’ll tell you – mine contained a tube of roll-on glitter (perfect for one’s eyelids), that fancy mascara that came with a white primer on one end, bronzer, and an extra bra strap choker, just in case the one I was wearing mysteriously snapped. Sometimes, I’d throw in a Dr Pepper-flavored Lip Smacker for good measure.
I blame my current obsession with cross-body bags on my North Face fanny pack.
Whether you’re at a punk rock concert or doing the cha-cha slide on the dance floor, there’s still something so freeing about having full range use of both of your arms.
4. Graphic Tees
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If someone were to study my closet circa 2006, they would probably assume that I went to a lot of classic rock concerts and worked at a surf shop in Marina del Rey.
As we all know, I actually just spent a lot – and I mean a lot – of my allowance money in the t-shirt sections at Urban Outfitters, Delia’s, Paul Frank, and good ol’ mall staples like Hollister, Fossil, Hot Topic, and Abercrombie and Fitch.
I remember being about fourteen and getting into embarrassing, public pout-fests with my mom at Abercrombie because she never let me buy any of their tees emblazoned with (not-so) subtle sexual innuendos.
Gee thanks, mom! How else was I supposed to let the eighth-grade quarterback know that I wanted him to ask me to the Snow Ball?
Obviously, stopping by his locker after lunch to talk about The Fast and the Furious while wearing an extra small t-shirt advertising the fictional “Pucker Up’s Lemonade Stand” was my plan A.
It seemed like such an efficient method – I mean, if CosmoGIRL! magazine suggested it, it had to have some merit.
If that failed, I’d try leaving a cryptic subtext on my AIM away message. One complete with Ashanti lyrics and a few oF ~*thEsE*~ tHinGieS would certainly win him over.
A fool-proof plan, you guys. This is why I had so many boyfriends in middle school.
These days, I still love t-shirts, but now instead of the super tight and wordy variety, I now prefer my tees to be loose cut and plain. Seriously. My white v-neck collection is so vast, that even Simon Cowell would be jealous.
However, I’m not ashamed to admit that I sometimes whip out my lucky Good Charlotte t-shirt to sleep in. After all, it was the shirt I was wearing when the eighth-grade quarterback told me my checkered Vans were “dope.” He SO had a secret crush on me.
5. Hoop Earrings
Before I had my pearl studs, Michael Kors watch, or lucky Eye of Providence ring, I had my trusty pair of silver hoop earrings, and they’re present in approximately 85% of all portraits of me taken between 2002 and 2007.
Sure, I had a healthy assortment of flashy chandelier earrings from Charlotte Russe, but those always seemed to tangle in my hair or irritate my delicate ear lobes.
I owned both shark tooth and puka shell necklaces, but those seemed to only work with pastel-colored Bermuda shorts.
And yes, I was not a stranger to rubber bracelets or studded leather cuffs procured from Hot Topic, but there are only so many days in a row that a girl can wear thick black eyeliner before it starts to take a physical toll.
But, my friends, the hoops were the perfect combination of sexy and cute. They worked with everything, from Roxy sundresses to (#1) distressed flared jeans and a (#4) graphic tee.
Remember the John Mayer song “83” when he wonders what happened to his lunchbox and why no one consulted him before throwing it in the trash? That kind of 2000s high school fashion perfectly describes how I feel about hoop earrings. Suddenly and overnight, these things just fell off a sartorial cliff.
I’m so happy to see the return of these in the 2020s — it’s about freakin time!
6. Pullover Hoodies
My pullover hoodies pretty much vanished into oblivion the day I started college, along with Total Request Live, my youthful metabolism, and the fortitude required to wear two polos at the same time.
But for a hot minute (or okay, the first eighteen years of my life), I rocked one of these at least once a week.
In college, I turned to yoga pants, North Face pullovers, and Nike Dunks for my lazy days. Before that, though, nothing said “I’m not trying too hard today” like a pullover hoodie, (#1) distressed flared jeans, and a full face of iridescent make-up.
Back then, you could up your cool points by scoring one from your brother or boyfriend – it was very Serena van der Woodsen-chic, but the book version of Serena, not Blake Lively.
Hoodies have actually stood the test of time, although the Aeropostale graphics are not the hit on campus that they once were.
Don’t be too hasty throwing these babies away, though – just as denim vests and leggings have both made comebacks, I have a feeling that logoed hoodies and windbreakers are bound to make a mainstream appearance any season now.
7. Ugg Boots
Out of all of my high school staples, Ugg boots seem to be the only item on this list that made frequent cameos on my college campus.
Actually, “cameo” isn’t a strong enough word. If my college life was a movie, Uggs would win a Razzie for Worst Supporting Role.
But, I digress. This is a list about high school, and when it came to that period of my life, a standard-issue pair of Uggs was better than Christmas, Homecoming, Valentine’s Day, and the last day of school combined! A must have on your 2000s high school fashion.
In high school, I was the proud owner of three pairs of Uggs. I wore them both over and under my (#1) distressed flared jeans from September to April. Back then I even bought a special spray from Saks that made them somewhat water-resistant.
I had knee-length ones and a calf-length pair and even had a hard leather pair, which proved to be extremely useful in the ice and snow.
Now, I’m definitely not a bonafide Ugg hater or anything. There are definitely worse footwear choices, like platform flip-flops.
There are a few occasions when Uggs are perfect, like a late-night study session in a creaky old library or if you happen to be surfing on a cold beach (you know, what Uggs were originally intended for). And you know what? Uggs are back in 2022!
The only time I’m against the Ugg movement is when they’re worn at a ridiculously inappropriate time. For instance, with a dress. Or with Nike shorts. Or in temperatures above 45 degrees. Worst of all, when they’re worn with the next thing on the list…
8. Denim Skirts
Senior year of high school, I begged my mom for months to buy me a Rock and Republic denim mini skirt.
I told her that I would wear it for years, that it was an investment piece. Finally, as a graduation present, my mom bought me the most perfect dark-washed mini, complete with the signature “R” back pocket design and the perfect amount of fraying at the hem.
Did I ever wear it again past that summer? Of course not. But in high school, it was at the top of my wish list. You can’t rock your 2000s high school fashion with out this.
I was a sophomore when my crush Seth, who was a really popular senior and a teacher’s aid in my drama class, told me that he thought it was adorable when girls wore denim skirts with (#7) Ugg boots.
From that point on, it was over.
I might not have had a designer denim skirt yet, but I rocked my Aeropostale one with Uggs to every single football game, pep rally, or even if I just happened to be within a 3-miles radius of his house.
Sure, my feet felt like stuffy and clunky hot messes, but how could I risk bumping into him when I wasn’t dressed my best?
A few months later, he kissed me in the costume closet during after-school rehearsals for the school play, Shakespeare’s As You Like It. Later, I wrote on my Xanga page that it was the best day of my life.
Yeah, I guess I wasn’t one for subtlety back then.
9. Goody Cloth Headbands
Maybe I liked the pretty color assortment. Perhaps it was because you could pick up a 5-pack for $3 at any Walmart or CVS. Probably it was because I ran cross country, and my oh-so-chic (yet oh-so annoying) cheekbone-length bangs were constantly slipping out of my ponytail and onto my face.
Whatever the reason, I rarely left home without one of these suckers affixed to the crown of my head.
Nowadays, I’ve graduated to fancier hair accessories, like leopard print knot headbands, throwback scrunchies, blingy hair clips, and even the occasional tape-in hair extension. A huge style factor during 2000s high school fashion.
However, I’d be lying if I didn’t admit to missing the good ol’ days of butterfly clips, teethed headbands, and ‘do-rags. There’s just nothing in the world that feels quite like being immaculately accessorized, you know?
Also Read: Our Favorite Preppy Headbands
10. Velour Sweatsuits
You know you secretly sang Avril Lavigne’s “Things I’ll Never Say” at the top of your lungs in your bedroom into a hairbrush microphone. You know you teared up when you heard Bennifer broke up. And you know you rocked a velour sweatsuit with (#5) hoop earrings and (#7) Ugg boots on more than one occasion.
This particular trend took my little suburb by storm. Everyone from soccer moms to teeny boppers had a set!
These sweatsuits, however, were not made for exercise. Trip to the mall? Yes. A study date? Sure. To meet grandma for brunch? No, my dad made me change into something less skin-tight.
With a pair of (#5) hoop earrings? 100% absolutely. But for anything that required physical exertion? No sir, that’s what Soffe “CHEER” shorts and (#4) graphic tees were for.
Much like what happened with my designer (#8) denim skirt, by the time my mom caved and bought me a Juicy Couture tracksuit, I went off to college and this baby, along with my StuCo t-shirts and track spikes, vanished into the oblivion of my high school closet.
Still, you can’t help but appreciate the novelty of this item. My Juicy suit is practically in mint condition – I know it’s going to come in handy one day for a “Jenny From The Block” Halloween costume, or even several years down the road as an authentic vintage ensemble!
11. Tattoo Chokers
Does anyone else remember buying stretchy chokers with the tickets they earned at the arcade?
At arcades (or you know, movie theaters with large lobbies) I was always partial to playing Skee Ball. Unlike regular video games, they were easy to figure out, and unlike the game where you slam gophers in the head with a puffy bat, you didn’t look completely ridiculous playing it.
Plus, hello – the ticket payout dividend was always substantial, comparative to the number of coins required to play. Who knew that at the age of 13 I’d already be thinking like an economics major?
Stretchy tattoo jewelry came in black and rainbow designs, beaded or plain, for both your neck and for your arm.
Of course, I was 4’8″ until ninth grade, so the chic ones that were made to go around your wrist only fit my ankles. Stupid #latebloomer problems!
Now, I’m not going to say that this was the most awful accessory I’ve ever owned. (Just a few years ago in my freshman year of college, I did once wear a plastic baby barrette in my hair.)
But why we were all so obsessed with stretchy necklaces that resembled tacky drawn-on tattoos (and why they are coming back) is completely beyond me.
12. Wrist Sweatbands
Confession: in 8th grade, I went through a bit of a punk-rock phase.
Avril Lavigne had just been introduced to the world, I adored watching Sum 41 and Simple Plan on TRL, and the only boys who paid attention to me all wore those weird pants with straps criss-crossing loosely along the back of them. (Sidenote: how is it that I never saw any awesome accidents resulting from carelessly wearing those?)
I experimented with black eyeliner. I used “pieces of flair” I bought at Hot Topic to cover up the Abercrombie logo on my jean jacket. Begged my mom for a pair of chunky skateboard shoes and could never really remember the difference between The Hives, The Vines, or The Strokes.
I knew that people would see my studded belt and black fingernails, and automatically assume I was a badass.
My parent’s wouldn’t let me wear a tie to school (à la Avril Lavigne), so instead I completed my look with a sweatband on both of my wrists. I had one pink Hello Kitty design, and the other was blue and white striped.
Now, I have no idea what I did that could possibly work up enough physical exertion to require a sweatband, but nonetheless I was more than prepared for the occasion.
Oh yeah, I decorated said wristbands with a couple of extra-large safety pins. I was hxc.
13. Surfer Chic Attire
After 8th grade, I wasn’t nearly as angsty and soon decided that if I wanted to get a boyfriend I could take home to my parents, I had better start dressing like a girl you could take home to your parents.
Not wanting to totally give up my non-mainstream style, I settled in on punk’s sweet and friendly cousin – surfer chick chic.
Now, I grew up in Oklahoma. I was completely landlocked, but you would have no idea by the way I dressed.
I owned slip-on Vans and board shorts. Back then I thought lounging on piers in your swimsuit while snacking on popsicles and checking out a bleach-blonde guy’s surfboard was a completely normal activity.
My new wardrobe was pretty convenient, because it gave me an awesome excuse to proudly rock distressed (#1) denim flared jeans from a “preppy” store with (#12) wrist sweatbands acquired at Hot Topic.
I worked at PacSun the summer between my sophomore and junior year of high school, but rarely took home an actual paycheck on account of taking such advantage of my employee discount. Puka shell necklaces? Check.
I also unsuccessfully tried to salt spray scrunch and Sun-In my hair on multiple occasions.
This is pretty embarrassing too, but my very first AIM screename was some derivative of the phrase “FoxyRoxy.”
Whether you preferred Roxy or Hurley, Hollister or Paul Frank, you know you were just drawn to the bright colors and breezy feel of surf-style clothes at some point in your teen years.
14. Tiny Purses
In high school, I didn’t even realize that this was a fashion trend. I just thought all purses were teensy and made to wear over your shoulder, right under your armpit.
Now, I realize that these purses became popular because they were the most inexpensive model that designers offered, therefore the only ones your parents were willing to pay for.
Nowadays, while I love my mini bags, I have branched out in the bag department. I have all sizes of purses now, and I love switching it up.
How did I possibly survive with only such a minuscule purse?
I mean, iPhones weren’t even invented yet, so you had to somehow fit a digital camera in there too! Plus a brick-like cell phone…keys with several large keychains attached…and a full make up case (you know, just in case of emergency). Craziness.
15. Colorful Polos
There were three things that I took very, very seriously in high school:
- Getting the newest Gossip Girl and A-List books the day they came out
- Attending varsity basketball games early enough to get a seat close to the bench
- Making sure I had a polo representing every single color of the rainbow
Perhaps it was my obsession with Gossip Girl that made me so interested in obtaining a polo shirt from either Ralph Lauren and Lacoste.
Sure, I had your run-of-the-mill American Eagle and Abercrombie brands, but to me, that tiny little embroidery was more like a mighty badge of honor.
I remember going to Saks 5th Avenue after school, praying that an Easter egg-colored polo in my size would end up on the sales rack. Sadly, my prayers went unanswered.
In college, I feel like most girls either LOVE polos – frequently accessorized with pearls and a preppy color scheme – or completely hate them. I was in the latter camp – I guess my Lacoste lust in high school wore me out!
16. Tacky Underwear
This is awkward, I know…but my mom refused to buy me thongs growing up (this was right at the peak of the thong trend – thanks Sisqo!), so I used to buy the 10 for $25 thongs from Charlotte Russe, stash them under my bed, and hand wash them in my sink.
No one but me and the girls in my gym class knew I had them, but I felt so cool just knowing I had them on.
Man, I was freakin’ rebellious back then.
It didn’t stop at thongs, though – if it was lacy, neon, sequined, or made from polyester and could be called underwear, I was in. Same story when it came to bras and camisoles.
Nowadays, you couldn’t pay me to wear anything besides cotton down there. Thongs, though sometimes necessary, in my heart of hearts have never, ever been something that I’ve enjoyed wearing.
The only tub full of underwear you’ll ever see me dig through now is the bikini-cut pile at Victoria’s Secret‘s semi-annual sale.
Years before Air Force 1s got their second fashion wind, I was wild and crazy about my Sketchers.
Sure, they were too clunky to actually run or do anything athletic in. I mean, just look at them – they look more like rubber hiking boots than they do running shoes.
This was especially true when it came to the slip-on athletic and canvas styles. Slip-on tennis shoes? Those were little more than comfortable fashion statements. But, a fashion statement they were.
Most people had the standard baby blue pair, but I bought mine while on a family trip to Dallas, so my Sketchers were pink and navy. And let me tell you, I cherished the heck out of those puppies.
Somehow in 8th grade gym class, I got away with wearing my slip-on sneakers every day. It was middle school gym class, so we pretty much stuck to playing kickball or watching the boys play touch football.
One fateful day though, I left gym class, stashed my shoes safely in my trusty Gap drawstring backpack, and promptly left them laying on my lunch table on my way to choir class.
To this day, I’m still a little heartbroken over it – and well, I think my mom is still ticked.
18. Capri Pants
For those days when it was too unbearably hot for pants but too frigid inside of your classroom, you had one awesome alternative to turn to…the capri pant.
These came in an assortment of styles, most classically a skinny denim pair, or a loose-cut khaki cargo pair. (P.S., just typing that sentence made me cringe!)
Another awesome option – you know, just in case you wanted to be fancy – was the flowing, bell-shaped Palazzo style, best worn with a pair of heels and a wooly turtleneck sweater. Wait, that was just me? Dangit!
We also shouldn’t forget about the capri’s not-so-distant relative, Bermuda shorts. If your school had an iron-clad shorts inseam policy, you probably loved them as much as I did.
Marissa Cooper made plaid Bermuda shorts look so breezy and (#13) Surfer Girl Chic when she paired them with a (#15) polo and a sporty pair of slip-on Vans.
In college, you still see the occasional capri pant – but of course, only in the form of Lulumon yoga tights.
I can’t say this trend is one that I really miss. I had huge calves when I was young from ballet, and rather than being proud of my strong legs, I was weirdly ashamed of my presumed “cankles.” Yeah, I was an odd kid.
19. Puckered Shirts
There’s no cutesy way of framing this 2000s high school fashion one. I have no funny anecdotes connected to it. When I think back and remember puckered shirts from Limited Too, all I wonder is why the heck my mother let me buy one!
Of all the fashion faux pas from my past, this is the one I’ll look back on with the most awkward sense of shame and regret.
Its odd, shapeless construction was hardly flattering, and seemed to only highlight the fact that I didn’t start puberty until I was 15. The ombre design (before ombre was cool) looked like a bad tie-dying job. Plus, people would constantly come up to you and want to rub your sleeves or pull at your collar.
There is literally nothing redeeming about these shirts that I can think of.
This, my friends, just might be the silliest thing our generation brought to the masses.
20. Peasant Tops
Around the time we were in middle school and early high school, ’60s and ’70s fashion had a bit of a Renaissance. Bell-bottoms were everywhere, platform shoes were super hot, and any shirt with puffy sleeves and made from gauze-like material became the coolest thing on the block since Even Stevens.
Speaking of the Disney Channel, it was none other than Hillary Duff herself rocking 2000s high school fashion peasant tops on Lizzie McGuire that made me beg my parents to take me to Old Navy to snag one for myself.
She always wore them with a perfect pair of foamy platform sandals, a (#11) tattoo choker, a knee-length skirt, and her bangs pulled out of her face in a perfect single braid along the side of her face.
Kudos to the Duffster – out of all of my childhood icons, it kind of seems like she was the only one to grow into a mature, functioning adult without getting into too much trouble along the way. Plus, her husband and kids are completely adorable. What a class act!
So, they might be a little too flower-child-esque to pull off at the moment, but I’ll give credit where credit is due. These shirts could be pretty flattering if you had the right style!
They looked awesome with a (#18) pair of capri pants, and helped give off a cool, Californian (#13) surfer girl vibe.
Did you own these pieces? Or did we leave off one of your faves? Tell us about it!
I just shared my high school and middle school closet staples, but now I want to hear all about yours!
What was your favorite outfit in HS? What was the most cringeworthy thing you loved as a teen?
If you’re currently in high school, what are the big trends you’ve noticed? Did you have a North Face fanny pack, or a Juicy sweatsuit? What about a pair of Birkenstocks? Are you ready for flared and boot cut jeans to come back in style?
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- The Ultimate Guide to Y2K Fashion
- 2000s Fashion Icons: Beyoncé
- Five 2000s Fashion Trends That Are Ripe for a Comeback
- How to Wear 2000s Fashion Trends Today
Leave us a comment and share some of your funny, awesome, or embarrassing fashion stories from your teenage years. We can’t wait to hear you spill!