Every now and then, you’ll see a photo of a fashion moment from years gone by so disastrous that you physically cringe. Of course trends come and go, but there are some looks that should really have never seen the light of day. And no one is ever immune to wearing a dodgy outfit – not even stars on the red carpet. Here are the most embarrassing celebrity fashion moments from the 1990s.

10. Pamela Anderson, 1999

Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

First up is Pamela Anderson at the 16th Annual MTV Video Music Awards, sporting 1. a pink fluffy cowboy hat, 2. a corset, and 3. bejewelled trousers.

There’s a lot going on here. It’s not so much that the individual items of clothing are bad – it’s more that they don’t work together. This outfit is overkill. Still, it’s weirdly comforting to think that even the Pamela Anderson doesn’t look flawless 100% of the time.


9. Kim Basinger, 1990

Credit: Vinnie Zuffante/Michael Ochs Archives/Getty Images

Kim Basinger attended the 62nd Academy Awards with her brother Mick back in March 1990. Interestingly, Basinger decided to design her own dress for the occasion.

The result was a white satin gown, which doesn’t sound too bad, only Basinger decided to get creative and make half of the dress in the style of a blazer. The design was universally panned and has since been remembered as one of the worst Oscars looks in history.


8. Christina Aguilera, 1999

Credit: Brenda Chase/Online USA/Newsmakers

Christina Aguilera attended the American Teacher Awards in Los Angeles in November 1999 wearing this blue satin monstrosity.

It’s an interesting style choice – the excess of fabric, the dull grey-blue colour, the crease-prone satin. Even the tube top and low-waisted skirt combination is questionable. At least we can say that this outfit is quintessentially 90s, if nothing else. (Even if it represents all the worst aspects of 90s fashion).


7. Meg Ryan, 1999

Credit: Brenda Chase

Back in January 1999, Meg Ryan attended the Golden Globe Awards wearing this unorthodox ensemble.

There’s a lot that’s not great about this look: the colours are pretty bad for starters – khaki and pastel yellow is not a winning combo, it seems. The fit also isn’t great, and somehow manages to make Ryan look frumpy. It takes a lot to make Meg Ryan look bad, but it’s fair to say this outfit does the job. At least her makeup looks good, right?


6. Reese Witherspoon, 1999

Credit: Brenda Chase/Stringer

Pictured above is Reese Witherspoon at the premiere of Cruel Intentions in 1999. While Witherspoon still looks cute, this outfit doesn’t exactly scream ‘red carpet glamour.’

From the ill-fitting top to the (frankly) ugly skirt, this is definitely one of Witherspoon’s worst looks – if not one of the worst looks of the 90s.


5. Susan Sarandon, 1996

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Susan Sarandon wowed crowds at the 1996 Academy Awards – and for all the wrong reasons. Her dress – a Dolce & Gabbana copper ballgown – wasn’t the most flattering fit or colour. The dress was eventually acquired by the Costume Institute at New York City’s Metropolitan Museum of Art.

At least Sarandon did actually walk away with the award for Best Actress for her role in Dead Man Walking, which hopefully softened the blow of her outfit tanking.


4. Melissa Joan Hart, 1997

Credit: Brenda Chase

Melissa Joan Hart (of Sabrina the Teenage Witch fame) wore this little number to the premiere of Rodgers and Hammerstein’s Cinderella in 1997. There’s not a lot of good things to say about this dress – the pattern is too ‘busy,’ the fabric looks like it came from a granny’s sofa, and the green fur trim is questionable to say the least.

We’re sorry Melissa, but this isn’t your best look.


3. The Spice Girls, 1997

Credit: Vinnie Zuffante/Michael Ochs Archives/Getty Images

The Spice Girls hugely influenced 90s fashion – usually for the better – but occasionally even they got it wrong. Pictured here at the Billboard Music Awards in 1997, it’s fair to say that Posh is the only one who looks passable.

While the group often took risks with their outfits and managed to pull many of them off (see: Geri’s Union Jack dress, Mel C’s leopard-print jumpsuit), there were occasions where the girls went a bit too far. From Emma’s overly-sparkly blazer to Geri’s all-white get up here, it’s fair to say that the Spice Girls usually look a lot better than this.


2. Gwyneth Paltrow, 1999

Credit: Newsmakers

Gwyneth Paltrow is another star who usually makes admirable fashion choices – but even she’s made the occasional faux pas in her time.

Her outfit at the 1999 Golden Globes was arguably one of her worst looks. The black top and cardigan paired with the iridescent satin skirt was an entirely underwhelming ensemble. Paltrow went on to win the Golden Globe for Best Performance in a Musical or Comedy for her performance in Shakespeare in Love, but she was arguably the worst dressed in attendance that night.


1. Lil Kim, 1999

Credit: Brenda Chase/Online USA

Here’s rapper Lil Kim attending the 1999 Source Hip-Hop Awards in Hollywood, wearing a sparkly, sheer brown bodysuit with fur embellishments, paired with a white-blonde wig.

Lil Kim is still renowned for her daring fashion, but this is definitely one of her most ‘out there’ looks. It’s so iconic that it’s since been recreated by none other than Beyoncé herself. This ensemble might be remembered for all the wrong reasons – but at least it’s remembered, right?