Celebrity Outfits That Made Us Cringe In The Past But We Love Now

Celebrities are just like us in that they have made many fashion mistakes, except the difference is that theirs live on forever in our minds and on the internet. The '90s and Y2K eras were full of cringe-worthy styles that our favorite stars embraced, but which had fans asking, "What were they thinking?" We can't forget the time Björk wore the infamous swan dress or when Lady Gaga had on actual meat at the 2010 VMAs. Fortunately, that never became a trend and we can lock up the meat dress in the vault forever.


For other celebs, their cringey 'fits actually have aged well and we're all for recreating their former fashion misses. Like with all trends, past looks have made their way around again, and this time, we aren't hating on them. In fact, we're digging the modern take on low-rise jeans and rave-style butterfly tie tops. If those past looks were wrong, we don't want to be right and we can admit that we've changed our minds on these celebrity outfits from yore.

The low-rise jeans that every celeb wore during Y2K

When it came to waistbands in the early aughts, the lower the better. Pop stars such as Britney Spears and Destiny's Child wore jeans with itty-bitty waistlines so minute that they might as well not even have existed. Back then, it was customary to let your thong peek out and flaunt your midriff with a belly chain. And forget about bending over — the act alone would cause a serious wardrobe malfunction.


When high-waisted jeans became trendy again, a lot of us exhaled in relief the long breath we'd been holding in order to suck in our stomachs. Finally, jeans became our friends again and provided millennials and Gen-Xers with a nice, sturdy girdle. However, low-rise jeans have made a comeback, and at first, we quivered in fear. But taking a second glance at the modern designers' fresh take on them has us giving low-rise jeans our stamp of approval. This time, they're not so snug around the waist that we'll flash everyone when we sit down. Plus, the baggier fit is a lot cooler this time around.

Kate Hudson's 2001 Oscar's dress

Kate Hudson could arguably wear anything and look good in it, but her 2001 Oscars dress was a miss at the time. The long sparkly silver Stella McCartney number was slinky and hit all her curves in the right way but the curious cape-like addition to her shoulders made the look odd. It featured a mock turtleneck with fringe dangling over her chest and upper arms, which had a lampshade effect. Hudson, who was up for an Oscar for "Almost Famous," told British Vogue 10 years later, "I woke up the next morning in my bed post-awards and without a little statuette on my bedside. I turned on the television to find out I was on every Worst Dressed list possible. So I called Stella and we just laughed our a**** off and she said to me, 'Look babe, it was the hair wasn't it?'"


The moment must have haunted Hudson for some time because in 2023, she took to TikTok to defend the dress. Looking at past photos, she stated, "We were way ahead of our time on this. I encourage any thoughts — maybe we should take it out again. Should I rewear this and restyle it?" We answer her question with a resounding yes! Looking at it now, the design was indeed ahead of its time and would still look stunning on her now. Although, we think the hair needs to go. Instead, Hudson should go for a sleeker 'do that won't fight with the intricate gown.

Britney Spears' denim maxi dress

Britney Spears and Justin Timberlake wowed at the 2001 American Music Awards, but not in a good way. They took dressing as a couple way too seriously and showed up in matching denim ensembles — Spears in a strapless denim maxi dress and her then-boyfriend in a jean tuxedo complete with a cowboy hat. The "Baby One More Time" singer styled her 'fit with a bejeweled choker, matching bracelet, and a silver belt slung low on her hips. It was like a fever dream we couldn't wake up from.


With double denim trending again, we think Spears' dress would do very nicely now. Accessorized without the tacky Y2K costume jewelry and the purse that looked like it came from Claire's Accessories, the patchwork-patterned maxi is pretty in-style. It's definitely not something we would wear on the red carpet but for a casual date or lunch with friends? Slip on some platform wedges or combat boots and this look is a winner.

Mariah Carey's Emanuel Ungaro butterfly top

In 1997, Mariah Carey came out with her hit song "Butterfly" and completely embraced the theme. She wore butterfly everything and even got a tattoo of one on her lower back. We were all for Carey embracing her spirit animal as she had just gotten out of a stifling marriage, but the glittery rainbow butterfly top she wore to the VH1 Divas 2000 took the motif a bit too far. Worn with low-rise jeans, it looked out of place during the tribute to Diana Ross. Soon, the tiny tie-tops were seen everywhere and while they had their moment, they made their way into the vaults of the aughts.


Over 20 years later, butterfly tops have fluttered back into style and are being worn by celebrities such as Dua Lipa and Olivia Rodrigo. Hailey Bieber even wore a sequined purple one with baggy jeans to show off her growing baby bump in an Instagram post. We're ready to welcome back this trend, and while we don't see ourselves donning butterfly tops for a supermarket run, we admit it's a cute festival look.

The Beckhams' all-leather look

We get it — the Beckhams are a power couple and they wanted to prove it to the world by wearing matching all-leather outfits to an event in 1999. The couple even had similar white tops underneath their jackets and completed the look with black boots. "It just seemed like a really good idea at the time, you know? It really did. I think it was a naivety then. We didn't know about fashion," Victoria Beckham stated on "The Tonight Show Starring Jimmy Fallon" in 2021. She added, "We didn't care. We just had fun and we were like, 'Hey, let's wear matching leather.'"


While we wouldn't go as far as matching our all-leather look with our partners, Victoria's 'fit has aged well and it could definitely be worn these days. Rihanna wore a similar black jacket and pants in 2022, while Megan Fox opted for a purple leather tube top and matching slim-fitting pants. We just recommend saving this look for the cooler months, as full-on leather gear will have you feeling overheated during summer.