Fashion is nothing but one big series of “Gotchas” just like that. By the time you’ve heard of it, the cool crowd already scorns it as passé.
A long-sleeve shirt with a short-sleeved band shirt over it.
With a pair of cutoff khaki’s and Airwalks.
I went for the grunge look for a while. Took a few years for me to get out of the (comfortable) habit of wearing baggy flannel over a t-shirt and whatnot. Here are some of my recollections from the various “scenes” I found myself enmeshed in during the 1990s…
Part of the grunge look was the explosion in combat boots of all sorts-- not just Docs, not just combats with dresses. Nike and Reebok came out with combat-styled shoes, Poleclimbers became popular, Altama speed-laces and paratroopers were big. Army/navy stuff of any sort was popular, really. Pea coats, jackets, whatever.
Hemp clothing. Hemp shirts, wallets, shoes. Many times worn with little Lennon-style sunglasses with lenses in funky primary colors.
Blue-collar fashion-- bowling shirts and shoes, gas station attendant shirts. Wearing a work shirt with an embroidered name patch that said something like “Bob” or “Fred.” Work clothes of any sort-- Dickies, work boots. Wallet chains-- started normal. Like, a security device. Became trip hazards pretty quickly.
Ironic/out of place t-shirts; thrift for the most inappropriate logos, because in Bizarro-land, they’re the most appropriate! Wear a Debbie Gibson concert tee to a punk show, or (if you’re an older guy) proudly sport your “Girl Scout Lock-In 1991” shirt.
“Hardcore”/gutter/crusty punk looks-- watching pre-90s punk show footage, I’m always struck by how normal everyone looks. Conservative hair (mostly), white shirts and jeans… The 90s was when the ultra-stylized leather/spikes/Misfits-skul-painted-somewhere/etc. look actually became much more commonplace.
Raver fashion-- neon, metallic, reflective, glowing materials. Plastic jeans, “stacked sole” sneakers, candy necklaces, pacifiers, filter masks, lanyards hanging out of the pockets of your giant Marc Ecko pants, Cat-in-the-Hat hats, Charlie-Brown-squiggle-stripe yellow shirts. Or, alternately, Mondo-futuristic looks-- same materials, but muted and technological-looking (think Matrix), with arm braces, head gear, gas masks. Or, alternately, happy hardcore with smiley faces… or candy ravers with kiddie toys and lunch boxes… or…
Stylized generic “retro” looks from an indeterminate 1930s-1950s look for the swing crowd-- pompadours on men and women, stiff skirts, zoot suits, Mary Janes.
Less scenester, but a look that seemed to take root overnight across all levels of society among women, was the purposeful exposure of bra straps under thin blouse straps/strapless tops. It happened right around the time that it apparently became mandatory to hike a man’s boxers up above the waist of their pants (as opposed to letting the pants sag below the waist, exposing non-hiked underwear).
Being “Krossed out.” Wearing your clothes backwards like Kris Kross
Does anybody else remember JNCO jeans in the late 90s? Like these - absolutely huge leg diameters, often with ridiculous things on the legs.
Ugh. I had an ex-boyfriend who liked them because he could stick a 2-liter of Mountain Dew in his back pocket.
Remember how at the beginning of 1998, suddenly ankle-length skirts were the big thing? Within about the space of one month, suddenly they were everywhere. That lasted for several years, until fairly recently (and I liked it).
I remember that, how they even made the straps with rhinestones to flaunt that the strap exposure was deliberate. <gagging>
As much as I hate to admit it, I had a pair. My mom couldn’t believe how outrageously expensive they were (almost $60 IIRC). And yes, a 2-liter bottle could easily fit in the “back pocket”, which actually ran down almost the entire back of the leg.
BOOYA! braided belt!!
The ubiquitous preppy outfit at my college consisted of:
-brown suede Buck shoes or Duck Boot for bad (fowl?) weather
-baggy jeans from Gap or some place
-the braided leather belt
-Plaid flannel J Crew, Eddie Bauer or Abercrombie & Fitch shirt over a T shirt (probably Dave Mathews Band, Rusted Root or some other jam band) with a long sleve waffle T underneath
-J. Crew barn jacket ( a 3/4 length light coat with a corduroy collar)
-destroyed baseball cap - usually fraternity or school related.
I recall in the late 90s, going out with some friends and noticing how every college-age kid now looked like Eminem or circa “Oops I Did it Again” Britney Spears
WhyNot, I think we’re about the same age. Not only did we roll up our jeans to taper them, we’d pull our socks up over the cuffs. Extra points went to those who had two colors of socks coordinating with their shirt(s) – I remember the layered shirt look, too. I tried the extra socks routine, but my mother insisted that my shoes actually fit, so I couldn’t get all the extra bulk in there. Really, I can’t think of the things that I wore in middle school without blushing.
Early college years was black stretch pants, a turtleneck, a HUGE flannel shirt over top, and hiking boots with big thick socks. Hey, my boyfriend at the time thought it was really cute.
I do remember when women’s t-shirts had sleeves that didn’t expose your armpits. Actually, that’s one I kind of miss.
Seinfeld is a really good museum for nineties fashion. I mostly notice the gigantic eyeglass frames in the beginning of the decade (George) that got smaller and smaller.
BTW, I notice that frames are getting bigger again.
That’s right! I’d forgotten about that. It was like we didn’t quite have the balls to wear leg warmers, but “scrunch socks” were the next best thing! 
I just remembered something: babydoll tops.
They were for “hippie” chicks, especially the ones with floral print. They made you look pregnant. They reached their pinnicle in 1993-1994.
Chinese-style Mary Janes slippers were also the shiznat back in the 90s. Whenever I had to dress up, I’d try to get away with wearing my slippers–to my mother’s chagrine.
I loved those! I still am a sucker for the Mary Jane look in shoes. Several of my stelletto heel shoes have the Mary Jane look of round toe and the strap across the foot.
Also, platform shoes. And I don’t mean platform, I mean platform.
I used to love my Chinese Mary Jane shoes. It helped that my college was near Chinatown, so I could always go buy another pair easily. I had them in black, blue and red at one point.
I started college dressed in black from head to toe. Then I had a jeans and tank top phase, a babydoll dress phase, a grunge phase (which was mostly due to my hanging out with a group of flannel-and-Converse-wearing guys - I was the Elaine of that bunch), a Stevie Nicks phase, and, once I began temping, a slutty secretary phase. Of course, I toned it down on days when I was actually called to work, making sure to keep a jacket handy. I think the Ally McBeal tight suits were all the rage by then.
I love that look, but it works better on slim women. I could never pull it off without looking frumpy.
But I came back into this thread because I just want to clarify that my statement about the platform shoes refers to the fact that they were big in the 90s. I didn’t mention them to imply that I like them. I don’t like them at all!
Ok, I did have a pair, but that is before you could find a sexy pair of stiletto heels in upstate NY!
Hillary hair became quite popular.
I seem to remember in high school, in the late 90s, was tight CK or Gap jeans, cut to accomodated boots, and timberlands. Maybe this was just my school, though.
Gestalt
I recall jeans being more on the baggy side.
In college in the early 90s, our most chic “going out” outfits usually involved palazzo pants and bolero jackets cropped just above the waist. By the mid-90s, the palazzo pants had shifted to flairs.
Lots of black tights instead of hose, and prints and textured tights became more upscale and appropriate for the office (in the 80s, the wild pattern tights were more of a teen/club look).
I also remember lots of fleece – especially the lower quality fleece that turned into a mess of pills after one washing.
Swing dresses and coats in addition to the babydoll dresses.
Heh… I still have my old circa-1992-93 glasses. I only wear them around the house after I’ve taken my contacts out, but early one New Year’s day, the party guests that crashed on the floor took to calling me “Sally Jessy” after I wore the big-ass glasses downstairs.
Hell, my fiance calls me that when I wear them now.
As for clothing… I recall bright colors being more acceptable than today. I had shirts in a variety of rather bright, but not neon colors that would look kind of odd today.
I recall that in the first half of the decade, conservatively dressed women had these dresses with absolutely HUGE collars or something like that on them.
Mostly, when I was in college, (1991-1996), people wore a lot of t-shirts and jeans.