Tyra Banks' 2000 Oscars Dress Is One Of Her Personal Worst-Dressed Moments

Some people watch award shows for the competition. Other people watch them for the live performances. But for us, the biggest draw is always the fashion. Nowhere do stars turn up the sartorial volume more than when they're arriving to paparazzi-packed crowds at the Oscars, or the Golden Globes, or the holy grail of fashion, the Met Gala. And often, we're delighted with the designs on offer. But some red carpet outfits, celebs admit they regret — such as the infamous Academy Awards look bemoaned by supermodel and TV host Tyra Banks.

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"What is my biggest fashion regret? The list is long," Banks joked in a 2024 interview with Harper's Bazaar. But one particular ensemble seemed to be top of mind — in her very next breath, she took aim at the Barbie-worthy Vera Wang gown she wore to the 2000 Academy Awards. While we think Banks should worry more about her part in the worst-dressed red carpet trend of the '90s, the supermodel honed in on her unusually femme Oscars 'fit not only for its divisive girliness, but for the poor decision-making that led to the faux pas.

When you have the chance to work with an iconic designer for an award show look, it seems wise to heed their opinion. Unfortunately, Tyra Banks missed this memo back in 2000. "I went to Vera Wang for her to dress me, and she suggested this really beautiful, deep blue, beautiful dress," Banks recalled to Harper's Bazaar. But, perhaps caught up in the poppy tides of Y2K fashion, Banks vetoed the elegant gown for a bigger, brighter option. "I was like, Vera Wang, I don't want to blend in, I want to stand out! And so I chose purple. Lavender. And ... I saw her face, but she was like, 'Okay, you're the supermodel.'"

So Banks went full princess mode, donning a full-skirted satin-and-tulle silhouette that looked like something from "Sofia the First." Then she matched the look with long, loose mermaid hair, a sparkling necklace, and the most ethereal purple highlighter the era had to offer. Sadly, this fairy-tale aesthetic didn't land with the critics. Entertainment Weekly likened the dress to a costume from "Gone with the Wind," calling it "the night's biggest dud." And Entertainment Tonight declared that the Wang design "screamed bad prom dress."

Whether or not she agreed at the time, Banks has also come to rue her choice in the years since. "Vera Wang, you were right," she admitted. "That 'Little Bo Peep Has Lost Her Sheep' dress that I wore to the Academy Awards was a hot mess, and to this day, I apologize and bow down to you. It should have been navy." Alas, we'll never know if the blue gown would truly have been a better fit. But in Banks' defense, many armchair fashionistas actually enjoyed her hyper-feminine lavender dress.

We've all made style missteps in our time, some of which make us cringe to this day. So we can't help but respect Tyra Banks for owning her fashion regrets with humor. But did her pastel Oscars look really deserve all its harsh critiques? Modern-day fans aren't so sure. After her interview with Harper's Bazaar, Banks revived the dress discourse on her own Instagram account, writing, "The year was 2000. ... People had some opinions about this dress back then. It kinda feels like @arianagrande would wear it in pink today. What do you think?"

"I remember watching this live and thought that you were so beautiful!" replied one user. Another added, "I think they were just hating on a real-life princess doll." And one fan succinctly cheered Banks on, writing, "People will always have opinions. Do you. You look fantastic." Looking back, we can't help but agree. Did the model's girly Vera Wang gown break new ground in couture? Maybe not. But in our opinion, it was perfectly pretty, charmingly styled, and looked gorgeous against Banks' skin tone — in other words, what should have been a safe red carpet selection.

Of course, fashion is in the eye of the beholder, and this is hardly the first time our opinion has diverged from more outspoken critics. For instance, there have been several Meghan Markle outfits that didn't deserve all the hate they got from onlookers. When it comes to fashion, just like anything else, you simply can't please everyone.