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Last Updated on August 4, 2022
The 90s are often reviled for its music, fashion, and general style, but don’t be fooled by the naysayers – the 90s not only gave us some incredible fashion moments, but they also produced some of the world’s most well-known fashion icons.
Here are 15 of your faves, what they represented for the fashion world in the 90s, and what was their defining and most iconic fashion moment.
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#1 Courtney Love
There is no 90s fashion without Courtney Love, so there’s no other person who can open this list. Whether you remember her from her heyday or you’ve come to appreciate her in later years, you can’t deny that Courtney is THE poster child for grungy fashion.
Counterpart to none other than Kurt Cobain, Courtney had her own claim to fame by fronting her all-female grunge band, Hole, and by heavily influencing fashion and pop culture, as a w(Hole) – ha! – through her grunge fashion.
If you’ve never heard of Courtney, have never seen her, or haven’t been influenced by her in some way, girl – where have you been? She is the ultimate grunge babe that made trashy look chic. In contrast to all the perfectly poised Hollywood celebrities, she came in as a (really, really) imperfect rock goddess.
Checklist: All the Different Styles of 90s Dresses (And a Few Mistakes Along the Way)
#2 Winona Ryder
Other than her intense romance with Johnny Depp and the now infamous “Winona Forever” tattoo that has since been (sadly!) modified (“Wino Forever”, really, Johnny?), Winona was the darling of the 90s, the leading lady in cult classic films, and just generally a trend-setter.
The thing about Winona was that she was always so effortless. Nothing she ever wore felt like it was overly studied or perfected.
Sure, it helped that she was small and adorable (when does that not help?), but her “I just threw this on and I don’t care that much” tomboy-ish vibe was just the epitome of cool and had lots of us gals pinning up pictures of her on our mood boards.
If you’re too young to know what a mood board is, think of it as sort of like a real-life Pinterest board, only with magazines, scissors, and glue.
Read: What Was Life Really Like in the 90s?
#3 Alicia Silverstone
Ultimate teen icon, Alicia Silverstone’s claim to fame was most definitely her role as Cher in Clueless, which has transcended time and is one of those classics of world cinematography.
Yes, it’s not the most artistic film in the world, but it’s given us so much to be thankful for. These are our Absolute Favourite Clueless Outfits Details Decoded.
We have to talk about that one outfit – you KNOW the one – yellow blazer, with a matching yellow tartan skirt and knee socks. Nothing will ever be more 90s-preppy-teen-wannabe than that outfit, and it helped that whole plaid skirt revival thing that happened.
Of course, that was also aided by the punk movement, but – SPOILERS! – we’ll cover that in Gwen Stefani’s section.
Read: Celebrity Edition: What to Wear to a 90s Party
#4 Madonna
I mean…do we even need to talk about how much of a freaking icon Madonna is? Rivaling Cher in number of “eras” and reinventing herself throughout the decades, Madonna is just always relevant. The 90s were no different.
After a decade of big hair and fishnets, the 90s came with a lot of black for Madonna. Oh, and cone bras. That’s right, 1990 marked the birth of that particular garment that is now iconic in pop culture, and it was a creation by Jean Paul Gaultier, specifically for her and her Blonde Ambition tour.
A cone-breasted legend.
#5 Spice Girls
Okay, so we’re cheating a tiny little bit here, because this isn’t one icon, it’s five, but can you blame us?
The Spice Girls were I-C-O-N-I-C, and not just for the Brits.
Their appeal was huge, because there wasn’t just one of them, there were five, so every girl (or young gay boy) could find someone to identify with – I guess kids would call them “spirit animals” now? IDK.
Posh Spice, Baby Spice, Ginger Spice, Scary Spice and Sporty Spice, one for each taste, all had their own individual styles, according to their oh-so-cutesy nicknames, but they also had stuff in common that was so quintessentially 90s.
Their shtick was girl power, and the 90s were definitely all about it, including fashion choices. It was less about the male gaze, and more about the fashion, a fact which is made obvious by the sheer existence of platform shoes and the now immortal lyrics of their hit, Wannabe: “If you wanna be my lover, you gotta get with my friends/Make it last forever, friendship never ends”. You heard it here first, lads.
#6 Naomi Campbell
You didn’t think we’d leave some of the incredible 90s supermodels off this list, did you?
Naomi Campbell is about more than just clothes and style, she’s got a presence and a magnetism about her that are striking. Not to mention that the woman still looks exactly like she did 30 years ago, there’s some Dorian Gray shiz happening there.
She is the quintessential effortless supermodel, as she looked like a bombshell in anything she wore (and still does): jeans and a t-shirt, fur coats, tight dresses, leather pants, plaid, printed leggings, sunglasses perfectly perched on her head – she did them all, and she did them flawlessly. Your fave could never.
Read:
#7 Sarah Jessica Parker
Name a more fashionable 90s icon than SJP – I’ll wait. No, but seriously, Sarah Jessica Parker was THE icon to look up to, when it came to the latest and boldest fashion. No one made more daring choices on the red carpet. Well, aside from Bjork and that swan dress.
Of course, A LOT of SJP’s fashion notoriety comes via her character in Sex And The City, Carrie Bradshaw, our most beloved fictional fashionista. But SJP herself rocked some excellent frocks, not to mention her natural curls.
Stop whatever you’re doing and go watch SATC to get some inspo on how to wear a tutu as a grown woman and make it look high fashion, too. None of that Toddlers And Tiaras stuff.
Caution: It is known to produce a furious need to shop and may severely impact your purse strings.
#8 Jennifer Aniston
Is there anyone in the world who is not familiar with “The Rachel”? Sure, it looks a tad ridiculous now, among chic French bobs and balayage, but back then, her haircut was THE one to get.
With no Instagram to reference at the hairdresser’s, you either took a magazine cut-out or just said the code-word: The Rachel. Worked every time.
But that wasn’t the only thing enticing about Miss Aniston – her wardrobe was an object (or I guess several objects) of envy as well. Specifically, her Friends wardrobe.
Is it the most 90s thing you’ve ever seen? Yeah. But in the best way possible.
Jennifer Aniston manages to still look cute, rich, and polished in those choices, while looking at some of our photos from the same era just evoke cringe and the obvious fact that we did NOT pull off some of these trends.
Read:
We Binge Watched all 10 Seasons of Friends: Here’s Our Favourite Outfits for Each Cast Member
1995 Fashion Trends That Defined the Middle of the Era
25 Photos of ’90s Hairstyles You Secretly Still Love
#9 Elizabeth Hurley
Liz Hurley is known for two things: her romance with Hugh Grant, and being able to wear a tight dress like no other. Every appearance with Elizabeth Hurley meant a new mini dress to parade around, always flawless, always stylish, and always the reason of envy for all of us mere mortals.
We’re not saying we took magazine cut-outs of her dresses to seamstresses trying to recreate her style…but wouldn’t you? White was her color – and a super popular color, in general, in the 90s, along with pastels – light pink, light blue, lavender, they were essential to any stylish wardrobe.
Unfortunately, that also included frosty eyeshadow in those exact colors. We sure remember THAT, and if we didn’t, there are plenty of photos to bare witness.
Read: 41 Looks for That Upcoming 90s Party (Time to Relive Your Youth!)
#10 Kate Moss
The ONLY 90s supermodel, according to some (not trying to throw shade at Naomi, I promise), Kate Moss is another one of those divas that is just timelessly, incredibly cool. Sure, having that face, that body, and that IT factor is a huge part of it, but her fashion sense is impeccable, too.
If you see Kate Moss in a slip dress, you may be tempted to just give up, because no one’s ever worn one as well as she did.
Of course, we can say the exact same thing about mini skirts, and fur coats, and jeans with white t-shirts, and…and…and…you get the picture.
It turns out the waif look hasn’t quite fallen off-trend, so any choices she may have made 20 to 30 years ago (YIKES!) are still completely relevant today. Her impact is not to be messed with.
When she wasn’t gracing the world’s runways, looking perfect, she was busy looking perfect in her everyday life, along with her equally gorgeous boyfriends (I mean, have you seen her wearing matching oversized leather jackets with Johnny Depp? Yes, him again – Kate may have been the most glamorous rebound EVER).
#11 Princess Diana
One of the few elegant and understated icons on this list, Princess Diana was an all-around class act and an example of incredible poise, and not just because she was a princess.
In fact, it wasn’t necessarily the “princess-y” fashion appearances that made people go wild (although there is something to say about that incredible wedding dress, that train, and those sleeves…girl), but her casual, everyday wardrobe that truly made her the (fashionable) princess of the people.
She basically perfected the art of smart casual including jeans + casual blazer combo, aka the preppy look, not to mention her fab button-down shirts her incredible colors choices. Pinks, reds, purples, and cobalt blues, oh my!
There was no blending in or fading into the background with Lady Di. She wore her fashion proudly and boldly, and that’s why she remains an indisputable icon, so many decades later.
Read: 24 Preppy Clothing Brands that Will Turn You Seriously Ivy League
#12 TLC
If there’s one thing we can say about the TLC girls, it’s that they don’t want no scrubs, a scrub is a guy who can’t get no love from them…and also that they had incredible style that was extremely influential, especially on the RnB scene.
Like Spice Girls, there isn’t one girl, there’s three of them, but together, they represent iconic fashion. Their complementary outfits with unique, individually personalized details were all the rage and you’ll surely remember this type of mix-and-match look from other girl groups as well – Destiny’s Child comes to mind.
Like other girl groups, a big part of the appeal is that each member had a distinct personality, so everyone could relate to someone, whether you were ALL about T-Boz’s bowl cut, or Left Eye’s pigtails.
#13 Drew Barrymore
A very young Drew was just getting her taste of fame back in the 90s, but her fashion was fierce AF.
Her long, flowing hair (or short and curly), dark lipstick, and a fresh face paired with a grungy, almost tomboy-ish wardrobe of high-waisted light-wash mom jeans, white t-shirts and leather jackets made her the coolest kid around.
There are also some incredible pics going around of her in floral shirts with a headband on and big hold hoops, which I’m sure you can agree is A Look. You know the trend of the button-down shirt tied at the waist? That was everything in the 90s and she did THAT and very well, might we add.
And we haven’t even gotten to the fancy red carpet looks and the slip dresses that Drew wore, paired with mary-janes, because comfort is always cooler than stilettos. We’ll pretend we can’t see the cigarette she’s sporting in all the pics, the 90s were a different time.
Style Tips: A Throwback to Our Experimental Jeans Wearing Days
#14 Gwen Stefani
If we’re talking about female representation of 90s punk, it doesn’t get better than Gwen Stefani.
Still a part of No Doubt at the time, you know her from timeless classics such as “Don’t Speak” and “Just A Girl”. In terms of style, we saw her range from polka-dot tea dresses to crop tops and fishnets with micro mini skirts, not to mention the neon colors.
Let’s just say her style was the kind that got you major side-eye from grandma, teachers, and more conservative parents. But the pink hair is not a phase, MOM! It’s who I am! Well, it was who Gwen was for a while there, when she wasn’t sporting her famous white-blonde bob with her dark lipstick.
The only thing is that we were not all blessed with Gwen’s impressive physique, so the crop top + low-rise mini skirt combo rarely made the same impact as it did on her.
#15 Tyra Banks
Sworn enemy of Naomi Campbell and host of 406464875352 seasons of America’s Next Top Model, Tyra Banks is yet another super fab supermodel that shot to stardom in the 1990s and she hasn’t come down ever since.
If you want to feel bad about yourself, look at Tyra Banks wearing…well, anything. She could pull off any garment, any hairstyle, and any makeup. Including that pink dress when she played a life-size Barbie doll.
Otherwise, Tyra could be seen rocking the model-off-duty uniform: jeans, white t-shirts, button-down shirts tied at the waist, and even backwards baseball hats. And they all looked amazing, damn it!
Iconic fashion choices: white t-shirts, mini dresses, lots of denim and chambray, button-down shirts, hats
Let’s Pay our Respects: All Tribute to All Those Hats We Can’t Forget
Of course, the 90s gave us more than just 15 style icons, but these are the most representative, most fab, most iconic gals that made our childhood, adolescence, and adulthood SO much more glam.
Now, over to you … let us know who you rate as the top female fashion icon of the 90s …
