I tried very hard to look like I came out of a Delia's catalog or like an extra from the movie 10 Things I Hate About You. Maxi skirts, tank tops with skinny straps, combat boots, chokers.
I wore the khaki colored duckcotten jeans, but I sincerely thought they looked rugged and a bit distinct, circa 1999 and 2000. I guess I was a bit ahead of the curve.
Early high school: Full on grunge. Thrift store everything. Men’s Levi jeans (my proudest thrift store score) or cords, docs or chucks, thrift store ringer T, Pendleton flannel I stole from my dad. Pink streaks in my hair.
Later high school: pretty much the same but went a bit hippie/raver. Huge purple overalls I would wear over a thermal. Baby barrettes. Chunky Ecuadorean sweater. Also went a little preppy senior year(getting ready for college? IDK it was New England). LL Bean fleece, Northface vest (also thrifted!).
1999 - Occasionally grunge, occasionally goth. Lots of jeans and t-shirts (usually bands, but some movies/tv), often with flannel overshirt. Sometimes donned the fishnet on either legs or arms. Lots of cheap rings and purple lipstick. Most of my experiments with hair dye was in college but I did have black hair for part of high school.
Rayann from "My So-called Life" is the closest example to how my friends and I dressed, we called ourselves "Pippy Hunk" (Hippy + punk). I had the skunk stripe too, thanks to Jolen's creme bleach. 5 years later we would probably be called Hipsters, but I don't think we had that term yet in 98?
I alternate between Docs, weird fucking shoes that were probably made for clubbing, and men's skate shoes. My favorite two were a pair of baby blue Vans and a black corduroy pair from Puma or Adidas. I would braid patterns into the laces and then just slip them on.
I still have my floral docs purchased in 95. Some of the painted design has worn off, but they hold up.
I was a trend setter. In 1996, I started rocking “charter boat chic”. I grew up on the water, worked boats, loved to fish, and loved Jimmy Buffett. I wore straight leg Levi’s, Sperry billfish, 🌈 flops, t-shirts from fishing tournaments, fishing brands, and Columbia shirts. Costa Del Mar’s wheni had to explain what they were. This was before every effing frat boy in America co-opted it for white boy summers. No one else I knew dressed like that at the time. It was my own thing. I hung out with the surfers at my school, as they appreciated the water as much as I did, and appreciated my unique take on it. I signed yearbook’s with my nick name that sticks to this day. Cap’n.
Graduated in 2002
Freshman and sophomore year - I wanted to be an NBA baller / athlete, wore a ton of Nike
Junior year - Thought i was goth because i listened to Deftones a lot, wore all black and band shirts
Senior year - Decided i needed to dress with stuff from Gap and Express to impress the ladies
Semi trendy I guess. Plaid flannels of course, baby doll t shirts, slip dresses, corduroys, overalls, lots of floral prints, striped shirts and sweaters (like union bay style) timberland boots, Birkenstocks (Payless knockoffs of course), chunky loafers.
Graduated 97. Grew up in the suburbs but right on the line where it becomes rural. So it was a mix of rich kids and farmer kids. I kinda straddled that. Carhartt jackets, back when they were for real work. Took weeks for them to wear in enough where you could comfortably put your arms down! Nu-metal T-shirts. Jeans, I wanna say boot cut but that might have been a few years later. Converse all-stars and a cheap pair of work boots for the winter.
Edit: huge baggy jeans! Not bootcut. Huge jeans. Totally forgot about that. A huge pair of jeans and Carhartt jackets. Ha!
Hilfiger, polo, Nike, Marc ecko. I did have the all leather zip up Iversons, white and black pair. I don't dress like that anymore. Once I graduated and started construction, it just wasn't practical to spend all that money on gear I was going to mess up. A nice pair of Levi, a crisp button up and tough boots these days
I wore a uniform to school. It was a navy blue kick pleat skirt, white oxford shirt (short or long sleeved), if it was cold out we could wear a white turtleneck. We had a choice of sweaters. We could wear a sweater vest with a logo on it that matched our year’s color (green for freshman, red for sophomore, blue for junior, yellow for senior), a cardigan, or a long sleeved sweater. We wore navy knee socks or pantyhose and navy blue and white saddle shoes. As the class of 1994 screwed us over, we had a summer uniform of navy blue culottes with a white polo shirt.
Outside of school, I wore clothes from the Lerner Shoppe.
I went to private school and also wore a uniform, but it was more like a very strict dress code that changed a little bit every year if the student council complained enough. I wore Oxford shirts (blue, white, pink, or yellow) and twill pants (khaki, navy, olive or gray). We also had plaid skirts and we could wear a few colors of polo shirts and sweaters. I didn't mind the uniform, just went wild with my accessories and nails/hair. Glittery belts, chunky shoes, chokers, and butterfly hair clips.
I didn't really have a clothing style because it would have been taken away. I was expected to dress from a J. Crew catalog when in reality I was alternative. A lot of the cool shit I had "disappeared' in the laundry.
This was pretty typical for me in hs. C/O 2000. Except I actually cut the seatbelt out of my grandpas ‘56 ford pickup that was rusting in the backyard, and used a big safety pin to hold it together in back. Also, I wore a real condom on a chain. They now make charm that look like a condom to wear on a chain. lol
2002, I went through so many “phases” in high school, but the majors were goth, raver (candy kid, specifically 🫣🫣🫣), and then semi-grunge but also just tank tops, skinny jeans, and Chucks. Did a lot of shopping at Shirts n Things during high school and my main bands were Marilyn Manson, NIN, Skinny Puppy during goth and generally Incubus, Green Day, etc. during many of these phases.
C/O 96 and I remember wearing Silvertab Levi’s, baby tees, Skechers and Gazelles. Also had the standard issued Starter Colorado Rockies jacket in the winter, lol.
ETA: This was my senior year. I remember going through a hippie phase my sophomore year and wearing bell bottoms and peasant tops. Birkenstocks made an appearance too.
My HS clothing vibe was all over the place. -colorful silk button down from express with jeans
-men’s button down with ironic tie and jeans
-baggy t shirt with umbro shorts
unbuttoned flannel shirts with a white t-shirt underneath, Doc Martin boots, a choker length necklace with some beads and a whale tail charm on it, ripped jeans or sometimes a long gypsy style skirt with a white t-shirt minus the flannel (but with the Doc Martins) - yeah that was pretty much my high school attire and yes I graduated. I’m an early Xennial
Levi’s 501s, side zip military boots, Vans or Chucks, either a metal band shirt (Maiden, Metallica, Anthrax, etc) or a punk band shirt (Clash, Ramones, Dropkick) wallet chain, studded leather belt, leather jacket.
Honestly, not much has changed. Still wear 501s, still wear Vans or boots. Still wear metal and punk band shirts. Still wear a leather jacket.
98-02. It was all over the place. Lots of band tshirts (NOFX, blink 182, Nirvana shirts from middle school), wide leg jeans, skate shoes, and some baby tees and occasional long skirts, and then weird shit like these bright orange baggy pants from Hot Topic, with my smashing pumpkins tank top paired with a black mesh shirt to get around my school’s bullshit dress code for tank top straps. Worn with my black vans that I turned into checkerboard pattern with the help of a white out pen. Add lots of brightly colored plastic jewelry and some orange-tinted glasses belonging to my friend and crush who would turn out to be gay. What a time to be alive.
2000 - loose fitting shirt, baggy jeans, and comfortable shoes. I wanted all the cool band shirts, but I could only eesr what mom bought me. I've been making up for it ever since, lol. It was cathartic finally getting a Smashing Pumpkins shirt.
I wore mostly plain shirts (dickes or wranglers sleeves rolled up, with a T-shirt underneath) jeans and converse shoes. I basically dressed like a factory worker.
I worked before and after school, so my appearance was more for function. The cops also tended not to stereotype a kid who looked like a 60’s era auto assembly worker.
Backwards hat, jeans, and various t-shirts like Quick Silver and band t-shirts. Metal and classic rock shirts in the early years of high school. Oh, and my leather biker jacket.
2002
Went in Freshman year with jnco/wide leg jeans, graduated wearing low rise/butt crack jeans. Basic tee shirts, long sleeves and sweatshirts, usually referencing a band, movie or tv show. Wore Chucks pretty much the whole time.
I was a rave kid. But back then we were undercover. Didnt want to stand out. I wore Semore Solo baggy pants, Adidas Superstars, or Vans. Basic Tshirts and hoodies. Yes, I had a wallet chain. I was also almost always in a fitted ball cap. Everywhere I went, I had my teal Jansport backpack, and Walkman with large headphones.
2001 - NIN, Type O Negative, Marilyn Manson, White Zombie for majority of my high school years
Ripped jeans/cutoff black jeans and we're set for senior year.
Throw in some JNCO's and we have ourselves and outfit.
98-02
Hardcore band t shirts and other skateboard stoner attire
This was a pretty standard outfit for me, in 1997.
https://preview.redd.it/m3ojt0ryz07g1.jpeg?width=1000&format=pjpg&auto=webp&s=40370464661adcba0cf46734692c7bff0c166559
This is also a pretty standard outfit for both my teenage daughters in 2025
Yeah, at Thanksgiving this year, a 16 year old family member walked in in a pair of Jncos and a hoodie. Messed my 41 yr old head up pretty bad.
This was me. Add in baby tees, wide leg pants, frosted eyeshadow.
Who was wearing Carhartt jeans in 1996 except oilfield roughnecks?
I was. Got so much shit for it but my family was working class and didn’t have much money. Now it’s hip fashion.
Cholos
I dunno, 17 year old girls?
Dickies was the thing around here.
I wore the khaki colored duckcotten jeans, but I sincerely thought they looked rugged and a bit distinct, circa 1999 and 2000. I guess I was a bit ahead of the curve.
https://preview.redd.it/o7rrsrv4617g1.png?width=1200&format=png&auto=webp&s=e9d1f8a3a4a14f92849314066385daec4ce3417d
Excellent.
Graduated in 1996.
Early high school: Full on grunge. Thrift store everything. Men’s Levi jeans (my proudest thrift store score) or cords, docs or chucks, thrift store ringer T, Pendleton flannel I stole from my dad. Pink streaks in my hair.
Later high school: pretty much the same but went a bit hippie/raver. Huge purple overalls I would wear over a thermal. Baby barrettes. Chunky Ecuadorean sweater. Also went a little preppy senior year(getting ready for college? IDK it was New England). LL Bean fleece, Northface vest (also thrifted!).
I was cool, so I had knock off Birkenstocks from Payless with socks.
Moment of silence for 90s payless
1999 - Lisa Bonet was my style icon. My friends called it "hobo chic," I called it goth-flowerchild.
Goth, rocky Horror Picture Show, corsets, pleather pants, trenchcoats.
2001, cheap army surplus from salvation army near fort drum and a trenchcoat. Did not listen to music or see much tv. Was a social outcast.
(1997) I used to dress like a nerd. I still do, but I used to, too.
I was a nerd, wide striped shirt and khakis.
My wife still has one of mine in her closet.
https://preview.redd.it/ksrfsjxk617g1.jpeg?width=6144&format=pjpg&auto=webp&s=69ab17f136c0ed3daf96824528b56423ba629b1a
I still wear a rugby from high school.
1998 grad. Sum 41 wasn’t my favorite but this is exactly what my friends and I were going for fashion-wise
https://preview.redd.it/gu4wgzf9d17g1.jpeg?width=1000&format=pjpg&auto=webp&s=0c532320f15264db237c152f2a74f000c34fd577
I was a very complicated mix of gangster/preppy/skater/hippie and I won’t be taking further questions. But I had excellent style back in the day.
1999 - Occasionally grunge, occasionally goth. Lots of jeans and t-shirts (usually bands, but some movies/tv), often with flannel overshirt. Sometimes donned the fishnet on either legs or arms. Lots of cheap rings and purple lipstick. Most of my experiments with hair dye was in college but I did have black hair for part of high school.
2000-2004. Lots of band shirts and lots and lots of corduroy pants. I called my look and vibe "cynical hippie".
https://preview.redd.it/zj9h0oj9t17g1.jpeg?width=240&format=pjpg&auto=webp&s=14a4bd96ba5b2534dcc7eceb9aa6f79e31af5d2d
Rayann from "My So-called Life" is the closest example to how my friends and I dressed, we called ourselves "Pippy Hunk" (Hippy + punk). I had the skunk stripe too, thanks to Jolen's creme bleach. 5 years later we would probably be called Hipsters, but I don't think we had that term yet in 98?
I forgot about the chunky bleached hair stripe omg 😭
1997:
https://preview.redd.it/op3oww1t417g1.jpeg?width=474&format=pjpg&auto=webp&s=0477c5bc18f0080e56196d4badcfda7eaeb26d2a
My alt were Puma
I alternate between Docs, weird fucking shoes that were probably made for clubbing, and men's skate shoes. My favorite two were a pair of baby blue Vans and a black corduroy pair from Puma or Adidas. I would braid patterns into the laces and then just slip them on.
I still have my floral docs purchased in 95. Some of the painted design has worn off, but they hold up.
https://preview.redd.it/7rqj8k09a17g1.jpeg?width=960&format=pjpg&auto=webp&s=c0114bdd6e0aa98a51adffda2de0f59a0835795d
Me & some friends! Graduated 95
I was a trend setter. In 1996, I started rocking “charter boat chic”. I grew up on the water, worked boats, loved to fish, and loved Jimmy Buffett. I wore straight leg Levi’s, Sperry billfish, 🌈 flops, t-shirts from fishing tournaments, fishing brands, and Columbia shirts. Costa Del Mar’s wheni had to explain what they were. This was before every effing frat boy in America co-opted it for white boy summers. No one else I knew dressed like that at the time. It was my own thing. I hung out with the surfers at my school, as they appreciated the water as much as I did, and appreciated my unique take on it. I signed yearbook’s with my nick name that sticks to this day. Cap’n.
snowboarder/rollerblader/grunge boy that played soccer so also umbryo/addidas boy.. haha
also.. parted in the middle, bleached orange (trying to blonde as an asian, yup.. )
https://preview.redd.it/izpd5j6mi17g1.jpeg?width=5776&format=pjpg&auto=webp&s=b4c3ad3ec77dbd3261f33fa86e2c2a659b90f8ff
Baby poop brown leather peacoat, a charlie brown shirt, green courodoroys, and blue Adidas Gazelles.
I was super stylish in 98/99.
Graduated in 2002
Freshman and sophomore year - I wanted to be an NBA baller / athlete, wore a ton of Nike
Junior year - Thought i was goth because i listened to Deftones a lot, wore all black and band shirts
Senior year - Decided i needed to dress with stuff from Gap and Express to impress the ladies
Tiedye, corduroy pants, simple shoes. Graduated 1997.
Oh my God, the simple shoes.
Simpler times!
School 1997. College 1999. School it was uniform, College it was full on early nu metal in my group. Baggy jeans, chains and black shirts.
97'
Jeans, tshirt, plaid flannel tied around waist, brown doc martin boots and a hemp necklace
Graduated 97. Grew up in the suburbs but right on the line where it becomes rural. So it was a mix of rich kids and farmer kids. I kinda straddled that. Carhartt jackets, back when they were for real work. Took weeks for them to wear in enough where you could comfortably put your arms down! Nu-metal T-shirts. Jeans, I wanna say boot cut but that might have been a few years later. Converse all-stars and a cheap pair of work boots for the winter.
Edit: huge baggy jeans! Not bootcut. Huge jeans. Totally forgot about that. A huge pair of jeans and Carhartt jackets. Ha!
Outside of school, I wore clothes from the Lerner Shoppe.
I went to private school and also wore a uniform, but it was more like a very strict dress code that changed a little bit every year if the student council complained enough. I wore Oxford shirts (blue, white, pink, or yellow) and twill pants (khaki, navy, olive or gray). We also had plaid skirts and we could wear a few colors of polo shirts and sweaters. I didn't mind the uniform, just went wild with my accessories and nails/hair. Glittery belts, chunky shoes, chokers, and butterfly hair clips.
I didn't really have a clothing style because it would have been taken away. I was expected to dress from a J. Crew catalog when in reality I was alternative. A lot of the cool shit I had "disappeared' in the laundry.
https://preview.redd.it/14pw02hlb17g1.jpeg?width=2048&format=pjpg&auto=webp&s=5b1b7c2f00ee3a3ac61253bece41e3c9b2d99daf
This was pretty typical for me in hs. C/O 2000. Except I actually cut the seatbelt out of my grandpas ‘56 ford pickup that was rusting in the backyard, and used a big safety pin to hold it together in back. Also, I wore a real condom on a chain. They now make charm that look like a condom to wear on a chain. lol
Black chucks, 501 levis cuffed, punk band t-shirt of sorts, black hoodie... in 2000.
I still dress the same except new balance instead of chucks.
1992
Depeche Mode wannabe Dave Gahan , white Jeans Motorcycle Leather Jacket, U.S. Marines haircut
96/97: manic panic hair, latex and leather, hippie clothes, fake doc m, black dresses, Lolita style dress
97/98: secondhand sports wear from the 70s, baggy clothes, military boots, afro perm like hair, hippie clothes
98/99: orange hair, black clothes a la goth, 70s sports wear, military boots, very modest clothes every Sunday as I was in the church choir.
I was experimenting a lot 😆
2002, I went through so many “phases” in high school, but the majors were goth, raver (candy kid, specifically 🫣🫣🫣), and then semi-grunge but also just tank tops, skinny jeans, and Chucks. Did a lot of shopping at Shirts n Things during high school and my main bands were Marilyn Manson, NIN, Skinny Puppy during goth and generally Incubus, Green Day, etc. during many of these phases.
Class of 99. My wardrobe was anything from Structure.
Chucks, jeans, t-shirt. 24 years later; chucks, jeans, t-shirt.
1996 - Champion hoodie, camo pants or comically baggy jeans, Vans, close-cropped hair bleached blonde. Accessorize with an X Swatch and/or “Krishna beads” necklace
1999
Jeans, cute tops, floral skirts, platform shoes, slip dresses, sweaters, and flannels. My wardrobe was mainly from:
-Learner's -Express -Esprit -Bongo
A pair of Levi’s Silvertab Baggy Pleateds and a t-shirt or chamois cloth shirt. In summer board shorts and a t-shirt.
96
Low chucks
70s Levi’s from thrift store
Heavy metal t-shirt
Flannel tied around my waist
I still wear this
C/O 96 and I remember wearing Silvertab Levi’s, baby tees, Skechers and Gazelles. Also had the standard issued Starter Colorado Rockies jacket in the winter, lol.
ETA: This was my senior year. I remember going through a hippie phase my sophomore year and wearing bell bottoms and peasant tops. Birkenstocks made an appearance too.
My HS clothing vibe was all over the place. -colorful silk button down from express with jeans -men’s button down with ironic tie and jeans -baggy t shirt with umbro shorts
Shoes: converse, tevas, brown monk strap shoes
Graduated 94
Relaxed jeans and flannels over a tank top. And wide stripe long sleeve shirts and sweaters. I graduated in 1996.
2000 - loose but not huge cargo pants or cords, skate shoes, I had a sublime shirt that wore the absolute fuck out of.
This except poorer
2000 - Eddie Vedder grunge minus the appeal of being the vocalist for a huge band. So, slovenly dressed.
Gap sweaters, delia's, flannel shirts, overalls, plaid skirts, those pullover dresses that you wear with a turtleneck, dad's sweaters (1998)
All grunge with a Les Claypool from the 90s mop head undercut
Hat, flannel, hoodie, baggy jeans, skate shoes (Simples), discman and headphones. ‘98
Jnco, 26 Red, Stussy
Catholic School Uniform. Class of 2000.
2002.
Cargo pants and low top boots, or AE jeans and Sambas. Polo shirt or long sleeve graphic tee. Probably a wooden beaded necklace.
I wasn't trying to fit in or stand out. Just average.
https://preview.redd.it/4oupxioit17g1.jpeg?width=780&format=pjpg&auto=webp&s=bc17dec7634071a73f16b4805830d73c54a4ae22
99! That’s me on the right more or less
unbuttoned flannel shirts with a white t-shirt underneath, Doc Martin boots, a choker length necklace with some beads and a whale tail charm on it, ripped jeans or sometimes a long gypsy style skirt with a white t-shirt minus the flannel (but with the Doc Martins) - yeah that was pretty much my high school attire and yes I graduated. I’m an early Xennial
Honestly, not much has changed. Still wear 501s, still wear Vans or boots. Still wear metal and punk band shirts. Still wear a leather jacket.
Plain tees and sagging pants or shorts. When I lived up north I added jackets and boots. That’s it. All four years.
2003 - Oxblood Dr. Martens, Levi’s jeans, Misfits or Black Flag Tshirt, OD green bomber jacket.
JNCO’s (mainly Twin Cannons) and a band shirt ( The Misfits, The Deftones, Wu-tang, & Depeche Mode mainly) and Adidas shoes.
https://preview.redd.it/ulpail5p027g1.jpeg?width=1080&format=pjpg&auto=webp&s=8ec415c453965712d1e4f70826059223ce45c5fb
2002
https://preview.redd.it/7a3lcdsl027g1.jpeg?width=909&format=pjpg&auto=webp&s=d1f2ac7249f8ddc58dcf25669ecd42124a0863e9
The girl in the middle was a model. AP Spanish.
Carhart wasn’t a thing until the 2010
I guess I was early....
Jeans, sneakers and an NBA jersey. Either AI or the black 91 Rodman jersey.
2001= School uniform. Outside of school i was a nerd who did not follow fashion trends at all. Still am.
White T, blue jean shorts, and hightops... Every single day.
Grunge.
97 I wore like Structure jeans and long sleeve surf shirts
I was a mix of grunge and thrift store finds. And odd shoes like glittery white platform boots. Graduated 99.
I attended a very preppy school. I did not fit in.
‘95. Black coat, white shoes, black hat, Cadillac.
98-02. It was all over the place. Lots of band tshirts (NOFX, blink 182, Nirvana shirts from middle school), wide leg jeans, skate shoes, and some baby tees and occasional long skirts, and then weird shit like these bright orange baggy pants from Hot Topic, with my smashing pumpkins tank top paired with a black mesh shirt to get around my school’s bullshit dress code for tank top straps. Worn with my black vans that I turned into checkerboard pattern with the help of a white out pen. Add lots of brightly colored plastic jewelry and some orange-tinted glasses belonging to my friend and crush who would turn out to be gay. What a time to be alive.
Pseudo skater sparkle pink prep. I liked all things and did whatever I wanted. Graduated in 2002.
Ripped blue jeans, cobain t shirt, sambas
2000 - loose fitting shirt, baggy jeans, and comfortable shoes. I wanted all the cool band shirts, but I could only eesr what mom bought me. I've been making up for it ever since, lol. It was cathartic finally getting a Smashing Pumpkins shirt.
‘98 - skate company logo or band shirts, khakis or cargo pants or dickies, skate shoes
Hoodie
I wore mostly plain shirts (dickes or wranglers sleeves rolled up, with a T-shirt underneath) jeans and converse shoes. I basically dressed like a factory worker.
I worked before and after school, so my appearance was more for function. The cops also tended not to stereotype a kid who looked like a 60’s era auto assembly worker.
2002 Went in Freshman year with jnco/wide leg jeans, graduated wearing low rise/butt crack jeans. Basic tee shirts, long sleeves and sweatshirts, usually referencing a band, movie or tv show. Wore Chucks pretty much the whole time.
94-98. I had teal and purple jorts. What was I thinking?
94-98
I was a rave kid. But back then we were undercover. Didnt want to stand out. I wore Semore Solo baggy pants, Adidas Superstars, or Vans. Basic Tshirts and hoodies. Yes, I had a wallet chain. I was also almost always in a fitted ball cap. Everywhere I went, I had my teal Jansport backpack, and Walkman with large headphones.