The 90s supers

90s Fashion: The best fashion ads from the best fashion decade

In the 90s there were no smart phones, no social media, no 24 hour news cycle. If you wanted to know about something back then you had to do the work. In the case of Fashion, that meant going to the store and buying fashion magazines; or at least being willing to stand around for hours ‘just browsing’ until you were told to buy something or get out.

I think the decade you become a teenager is special and I consider my self lucky to have been around during the era of 90s fashion. The ads then were still, had no soundtrack or sound effects and you were never in a rush to skip them. I looked forward to seeing the ads often more than the content itself. They are captivating and made you dream. Here are some of the ones I’ll always remember.

Guess Jeans

Even before my obsession with Fashion glossies began , Guess Jeans was probably the first fashion thing I became aware of. I had just started grade school and knew little about clothes but I could sense that Guess Jeans were some form of status as all the older girls we were wearing them, and the older girls were always the cool girls. I remember seeing them in the bathroom, usually fluffing their bleachy blonde hair and putting shiny stuff on their lips. They wore them high and really tight tight like a second skin, and never with any kind of top that would cover the red Triangle logo on the back right pocket.

Getting them skin tight down the the calf was really important. There was a trick I’d see these girls use where they would pull them as tight as possible around the calf, then fold over the excess and roll them up at the bottom to keep them in place. I imagined it was necessary to do this in order to make sure your jeans didn’t cover your leg-warmer style slouch socks that became an extension of their high-top Reebok or LA Gears.

LA Gears

I remember Guess Jeans being the first fashion thing I really wanted fashion. I cared nothing for the socks and found the high-tops hideous but I really wanted the Jeans.

Fast forward to the 90s when Guess transcended 80s style to make it to a new decade. Claudia Schiffer was the first Guess girl I remember. I thought she was impossibly beautiful and it was Claudia in her Guess ads that started my bedroom wall postering obsession that lasted throughout most of high school. It was always exciting to open a new month of YM (I’ll admit it) to see a new one to add to my collection. You had to be extremely careful to press the spine of the magazine super flat so you could extract the ad, in tact, with no tears in order to get the most perfect wall collage.

At the time it seemed impossible that there could ever be someone more sexy and glamorous than Claudia, but then came along Anna Nicole Smith. Anna Nicole became insta-famous (which back then just meant instantly) when Guess campaign launched. The media loved her cinderella story, a poor single mom from Texas who at the urging of her then boyfriend, went to an open call for models, was ‘discovered’ and soon found herself on the cover of Playboy.

Cover Girl: Anna Nicole Smith has appeared on the cover of Playboy 47 times in 20 countries. 5x in the US.

Back then you couldn’t just look someone up on Snap or Insta and see pics of them IRL, sharing their struggle with acne or learning about their morning green-juice routine. All you had were the ads. Anna Nicole was total glamour, platinum blonde curls, smoky cat eyes, full-red lips, perfect teeth and cleavage that was risky but still sexy. I don’t think the term ‘plus size’ had even made its way into the mainstream yet and I remember them calling her voluptuous either, she transcended and was just Anna Nicole, superstar. She had a natural vulnerability which looking back, was probably added the je ne sais quoi.

If you don’t know the whole Anna Nicole story, it did not end particularly well. If she was here today perhaps the support millions of followers would have made a difference but we’ll never know. I will always remember lying on my bed, flipping through Guess Jeans ads, and wondering what it would feel like to be beautiful as she looked.

Anna Nicole Smith, Guess Jeans
Anna Nicole forever

Calvin Klein

In sharp contrast to the overt sexy of Guess jeans, there was a new kind of sexy that emerged in the 90s, almost a non-sexy sexy that started with one image.

This image started so much of what 90s fashion was. You may know Mark Wahlberg as the actor who made a whole series about being an actor, owns a chain of burger joints but back then he was Marky Mark of Marky Mark and the Funky Bunch and Good Vibrations was his biggest hit that could heard across high school gym dances.

The cover of Women’s Wear Daily, September 15, 1992 seems to attempt a play on ‘Marky Mark’ with ‘Calvy Cal’.

I think Kate Moss was maybe 18 and this shoot and these ads contributed to making her the defining figure for a decade. She had a raw, streetwear inspired aesthetic referred to back then as “heroin chic” and in an era of the “supermodel”, singlehandedly brought back the waif. 

We know now that this shoot was so traumatizing that it sent her into a depression. She told Vanity Fair, “it didn’t feel like me at all. I felt really bad about straddling this buff guy. I didn’t like it. I couldn’t get out of bed for two weeks. I thought I was going to die” Wahlberg had also said some less favourable things about her to the press, in Nuts magazine he is quoted as saying “I wasn’t into the waif thing. She kind of looked like my nephew…she’s a very pretty nephew”. Today their publicists would probably get them to hug it out on Twitter, the brand eating up the hype.

But even if I’d known back then that they had zero chemistry it wouldn’t have mattered because for me this picture had nothing to do with him and everything to do with Kate. I was in love with everything about her. And clearly it was not just me because this campaign revived Calvin Klein’s fortunes and cemented Kate Moss the next big thing for decades to come.

Donna Karan

“In Women We Trust”, Rosemary McGrotha as the American President. Peter Lindbergh, 1992.

Donna Karan ads were never the I put on my wall but I always remember finding them sophisticated and cool, never old. Perhaps a big more ‘business’ than i was looking for back then but nonetheless I would always say to myself, ‘yes, you’re going to wear a lot of Donna Karan one day’. (and years later I learned I was right but realized I could have more DKNY than Donna Karan but basically the same thing right?)

In 1992 this editorial-like campaign was the first to really show a woman on the Presidential campaign trail. It was a story over several pages, in black and white with the slogan “in women we trust” which always felt like a powerful statement. And at the time while I was only a teenager and owned no Donna Karan, I remember thinking that Donna Karan would be perfect presidential wear, fancy enough for meeting world leaders comfortable enough for all the traveling a President must have to do. I realized only year later how progressive and ahead of her time Donna Karan really was.

At the time, Karan told New York magazine that it wasn’t a “real feminist statement” at all—it was more of a commentary on the screwed-up state of U.S. politics. “It’s simply a statement that when times are bad—and this country is in trouble—you turn to the motherer, the nurturer,” she said. Karan said she wanted “In Women We Trust” to be timeless, not recognizable as any particular moment in time, since women don’t like to change clothes every season.

Forever timeless (and very presidential)

Tommy Hilfiger

Aaliyah 1997

Tommy Hilfiger in the 90s was really a pivotal moment in culture. In the 90s fashion started to make a mainstream crossover into music, starting with hip hop.

Tommy Hilfiger and with Destiny’s Child, when they were still four, at the Billboard Music Awards 1996

Somewhat ironic considering Tommy Hilfiger back then was probably like the essence of white-boy preppy America wear.

Tommy Hilfiger in the late 80s.

Today fashion and music exist as one and it would be hard to see one existing without the other. Could you imagine seeing Billie EiIlish or Cardi B without noticing their clothes? For the latter perhaps but it just makes total sense that Rihanna has Savage Fenty, Jay-Z Rocawear and that everyone on the billboard top 10 have a fashion collaboration at some point in their career not matter how short lived.

It seems like moment that really kicked it all off for Tommy Hilfiger was in 1992 when Mary J. Blige released What’s the 411? featuring Grand Pupa, who mentions Tommy in the song (watch on MTV Raps)

Well, I be Puba on this here
The n**** from last year
Girbaud's hanging baggy
Tommy Hilfiger top gear

It’s also interesting to note here the reference to Girbaud, (of Marithé + François Girbaud) and early sign of the not-yet-mainstream relationship between hip hop and fashion. Pupa says “I wrote What’s the 411? ‘cause that’s what I was wearing. Tommy was my new wears. In the industry, we always shout-out whatever’s fresh or whatever’s dope. At that time, I came up on Tommy Hilfiger, and I was rocking that for a little minute.”

And in 1994 Snoop Dogg performed on SNL wearing a rugby shirt, with a massive “TOMMY” across the chest. Almost overnight ‘street style’ was born and and Tommy Jeans blew up. I think this must have been the birth of the big-ass logo.

Aaliyah was probably one of Tommy Hilfiger’s biggest supporters. She was in the ads campaigns and did red carpets and music videos clad in the label’s jeans, boxers, and bandeaus. While a lot of what she wore was actually from the men’s line, she became an inspiration for the brand’s women’s collection. She was unique and her style is still referenced today.

Aaliyah for Tommy Hilfiger, 1997

Miu Miu

Into the early 90s, fashion ad campaigns featured exclusively models, supermodels if they could afford it. This is just how it was, models were models and actors acted, there was a dividing line and people stayed in their lanes. So when Drew Barrymore turned up in a Miu Miu campaign in 1994 no one really knew how to take it. “She’s not a model!?” But for us on the verge of being actual teenagers this was monumental. We all knew Drew Barrymore because she was in E.T., and everyone saw ET so we all kind of had this connection to her.

She was like the cool girl two grades ahead who you knew, but you know she had no idea you existed. She was cool, and she smoked, had funky hairstyles, and used actual swear words in interviews.

Most of all, she had the impossibly thin Marlene Deitrich skinny eyebrows every girl wanted in the 90s. She ticked all the boxes and up she went on my bedroom wall next to Anna Nicole.


Gianni Versace, Sprint Summer 1993 by Richard Avedon.

The Versace ads were the ones I looked forward to the most. The most fantastical creations in prints and colors that somehow all came together so magically. It was ‘sooo Italian!’ which I had no really idea what it meant back then, I just know that I wanted it. The medusa head was so cool and Versace campaigns always featured all my favorites – Linda, Christy, Naomi, Claudia, Yasmin and Helena.

In the 90s wearing Versace had the power to launch careers, and many he did, many with just a single dress. It’s impossible to pick a single year that stood out, high fashion in the 90s really belonged to Versace.

Versace 1993, Richard Avedon
Yasmeen Ghauri, Versace


Gucci fall 1995, Amber Valletta shot by Mario Testino. The one I’ll never forget – I’d wear this today in a second.

Today when people talk about Gucci they talk bout Alessandro Michele, they talk about sneakers, they talk about NFT wearable collaborations with The North Face. But back in the early 1990s, not one was talking about Gucci, in a good way anyways. Gucci was known mostly for their leather accessories, and over-expansion combined with internal family feuding that almost tanked everything. Enough drama it seems that they could make a movie about it. Of course I knew little about the history of the house of Gucci but Tom Ford changed all that.

The 1995 Fall campaign ads were unforgettable. Sexy, sophisticated and so modern – it was everything people didn’t know they wanted.

Madonna in the exact look from the ad. 1995 MTV Music Awards.

I don’t think anyone could have predicted fashion’s almost overnight transformation from grunge and toward glamour. But this is what happened when Tom Ford took over at Gucci.

Today none of what you see here would get likes or reposts but in the 90s, Gucci felt so new, glamours and exuded well, sex. Tom Ford’s years at Gucci were strongly associated with provocation that had never really been seen before. 

The Gucci Thong, 1996 – so wrong but just so right.

Unsurprisingly, Kim has one.

Fern Mallis (who basically started New York Fashion week), has said that “He [Tom Ford] understood more than anyone else that sex sells.”

Amber Valletta has said similar, “Tom did something that nobody had done. He brought back an era of sex and glamour that hadn’t been around in a while; he brought back sex and and, I don’t know, like luxe gorgeousness.”

Looking back on these to they don’t seem incredibly risqué but back then these ads were basically porn, alluding to the voyeur, a new concept given mobile video was still a long way away – people ate it up.


Seeing as though the 90s were the height of the supermodel, it made sense that make up companies would want to get on board. When the first Viva Glam campaign launched, I had no idea what a drag queen was but I knew I loved RuPaul. Supermodel is still on my top 10 party songs playlist.

RuPaul was the very first MAC Viva Glam ambassador in 1994 and made Viva Glam an integral part of the brand’s identity. The campaign made him the first drag queen to secure a major beauty contract and the initiative it launched was unprecedented, with the entirety of proceeds from sales going to the MAC AIDS fund (which, since its inception, has raised more than $500 million dollars)

There was also some variations on the original that followed, this one featuring KD Lang alongside Ru. I believe the other guys is actually MAC co-founder Frank Toskan making a cameo.

The original Viva Glam: RuPaul + KD Lang

For its 25th anniversary (OMG really!?), MAC took some inspo from its archives and recreated the first Viva Glam campaign from 1994 with Winnie Harlow as Ru. Actually she apparently dressed up as RuPaul for Halloween and recreated the ad herself.

Hope you enjoyed this trip down the memory runway, would love to hear about your favorites.







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