Paris Hilton Will Never Live Down These Inappropriate Outfits

Paris Hilton's impact on fashion has been undeniable. In fact, with the current resurgence of aughts fashion, plenty of the best Y2K outfits Paris Hilton rocked in the 2000s serve as inspiration. Speaking of her style, Hilton told Hello! Fashion in 2026 that it was always about authenticity for her. "People didn't like the fashion I wore, but now it's everywhere. But people back then didn't even understand it," she said. "People said 'Oh, that's too much pink, too many sparkles' and now I love that fashion has caught up with me and people can have fun with fashion," the reality star said. "I've been someone who's always just been myself and I've never followed trends. I loved creating my own looks and back then I didn't even have a stylist, no agent, no publicist, nothing."

Now, while plenty of Hilton's looks have been iconic, the heiress has also worn a plethora of inappropriate outfits over the years. In particular, the star's clothing choices in the 2000s have left plenty speechless. And while she is one of the celebs who admitted they regret one of their red carpet outfits, we think she has plenty more looks to add to that list.

Paris Hilton attended a Gen Art: Fresh Faces in Fashion event in Los Angeles, California, in 2001, and the socialite arrived in a pair of blue sweatpants. She paired them with a simple navy tee, black socks, and platform sandals. Now, it was the 2000s, and fashion was rather wild, but showing up at any industry event in a pair of sweats seemed rather disrespectful. While Hilton was undeniably comfortable, a simple pair of jeans would have worked way better.

Paris Hilton's Y2K fashion was all about wild silhouettes and fun colors, and when she showed up to the Maxim Magazine Hot 100 Party in Hollywood, California in 2003, her satin pink matching set looked adorable. Sure, the skirt was short, and the top was cropped, but the look was a fun choice for the occasion. Until Hilton sat down on a motorcycle in her teeny-tiny miniskirt — needless to say, wearing a different outfit would have been much more appropriate.

In 2002, Paris Hilton attended an event hosted by Teen People, and for the occasion, she decided to wear a piece she was known for: an ultra-short mini skirt. Depending on the event, a barely-there skirt is totally fine, but as this was hosted by a teen magazine, a few more inches would have been more appropriate. The mesh top wasn't helping either, as it didn't cover much of the socialite's upper half.

There have been plenty of iconic celebrity naked dress moments over the years, and the truth is that a lot of them happened at inappropriate occasions. One of them was Paris Hilton's look for the 2025 pre-Grammy Gala. While the event isn't the show's official red carpet, glamorous fashion is expected, and Hilton's sparkly and sheer gown showed a tad too much. Still, as inappropriate as it may have been, there is no denying that Hilton pulled off the eye-catching piece.

Paris Hilton arrived at the Kerrang Awards in 2003 in a look that definitely didn't seem award show-appropriate. The reality star-turned-DJ wore a black lace bralette top and ultra-mini skirt, for a look that might have worked for clubbing in a warm destination, but not really a star-studded event. However, we have to give it to her, Hilton rocked bralettes as outerwear way before the trend kicked off in the 2010s

The noughties are known for their low-waist fashion, and Paris Hilton was always at the forefront of that trend. However, when she showed up at the 2003 MTV Movie Awards in an aqua blue matching set that was certainly more beach-appropriate, and the low waistline of her skirt was a risky move. In fact, it certainly seemed as if it fell lower and lower with every move Hilton made.