Inappropriate Outfits We Can't Believe Selena Gomez Wore

Pop star and actress Selena Gomez has had quite the stunning transformation. From being a Disney Channel star to taking on edgier projects like "Spring Breakers," Gomez has learned to push limits and find her own sense of style. However, her fashion journey has certainly been full of ups and downs. No star from the 2000s was really able to escape the bad style trends, and Gomez is no exception. While finding her fashion footing, Gomez took some big swings — and not all of them paid off.

Gomez's red carpet debut was in 2007. At the time, the rising star was just 15, so it shouldn't come as a surprise that she had a bit of a fashion learning curve. That said, swinging for the fences can lead anyone to wear some inappropriate outfits. From being too casual at a film premiere to attempting to pull off a sultry Kim Kardashian look, here are some of the scandalous outfits Gomez has worn throughout the years.

Red carpet fashion can be hard to nail, especially when you're a teenager, and at age 15, Selena Gomez completely missed the mark. Seen here attending the premiere of "Pirates of the Caribbean: At World's End," Gomez was far too underdressed for the event. In Chuck Taylors and skinny jeans, the "Wizards of Waverly Place" actress also fell victim to some of the more pernicious fashion crimes of the mid-2000s. The layered tank that was way too long was paired with a tiny vest. It was certainly a look of the era, but let's be honest, this outfit should never have graced the world premiere of a blockbuster film.

Taking risks with fashion can be challenging, especially since trends are always changing. Starting her career at such a young age likely made it difficult to know what to wear to work events. Luckily, since then, Gomez has debuted a new look, fully embracing more appropriate attire for red carpets. However, it did take quite the journey to get there, and there were certainly more misfires along the way.

While sitting down for a personal fashion retrospective with Vogue, Selena Gomez was quick to find an outfit that was an all-out staple of 2000s sleazy chic. While attending the "ABC All Star" party in 2007, Gomez laced up her white stiletto boots, threw on an oversized graphic tee, and admitted to being her own personal stylist. "I thought I was so cool, you guys," she told the outlet. And to be completely fair, this look really was a hot commodity in the 00s. A reminder that some things have aged better than others.

Luckily for Gomez, she continued to find a sense of fashion that helped her grow into her own — and leave the tiny vests behind. "I remember for the first time feeling like a woman," Gomez continued while referring to the first Vera Wang she donned at the 2015 Met Gala. Going from peak child star to elegant celebrity icon can be a rough transition, even with Gomez's stunning new makeover to help her through it. Although it is clear that Gomez has often opted for a sense of fashion that helps her feel comfortable, it might just be a little bit too cozy for the red carpet.

While we would never begrudge someone for being excited to find a dress that has pockets, wearing one on the red carpet can make the entire outfit appear overly casual. Seen here attending the premiere of "Ramona and Beezus" in July 2010, Selena Gomez once again opts for a look that's closer to rest and relaxation than the glitz and glam of a red carpet. Wearing white shorts, a white tank, and a flowing short-sleeved cardigan belted on top makes Gomez look as if she's in her pajamas and ready for a nap. The fabric itself also appears to be a jersey blend, lowering the quality and feel of the entire image. It would be one thing to show up in silk, but it's another to arrive in a fabric billed as "comfy." 

Taking risks on the red carpet doesn't come naturally to everyone, and Gomez is no exception. It would still take the actress several more years before she would be willing to explore more avant-garde options. Even then, not all of them were bangers — especially the ones where Gomez was trying to break away from her overly wholesome image.

While attending the American Music Awards in 2015, Selena Gomez was clearly trying to come out of her shell. With her straightened hair and skin-hugging red sequined dress, it appeared as if Gomez was trying to channel Kim Kardashian less than a year after Kardashian "broke the internet" with her derrière-revealing Paper Magazine cover. Whereas it is incredibly refreshing to see Gomez try to break out of her Disney Star mold, this dress didn't quite do the trick.

From the front, this dress is a gorgeous slam dunk. It fits well, the coloring is absolutely perfect for Gomez, and the styling looks sleek and sophisticated. However, when Gomez turns to the side to reveal how deep the plunging backline goes, it ends up looking bulky and tacky. Instead of a seamless backing that hugs around the hips, the hem is almost a beaded rope, sticking out and looking clunky. Where the dress falls on her legs is also unfortunate — the midi length often makes Gomez appear shorter than she actually is. It's clear that Gomez should leave the provocative outfit choices to Kardashian and her questionable fame.

As refreshing as it is to see how far Selena Gomez has come with her fashion since starting out as a teen, there are still occasional misfires. One such divisive outfit was the wonky dress Gomez wore for the 2024 Golden Globes, making her one of the worst-dressed celebs of the event. As striking as the red Armani garment is, the asymmetrical hem had us craning our necks to make sense of it. That, combined with the mismatched and knotted bodice, the dress just felt too all over the place.

For her part, Gomez loved wearing the dress, telling People, "I love the asymmetrical hemline. Having a cutout in the dress really felt edgy and fun." The best way to sell a tricky fashion choice is to have confidence in it, and Gomez certainly seemed confident in this piece. So much so that she just might have been caught spreading some rumors about Kylie Jenner while in attendance. Here's hoping Gomez will continue to take chances with her outfits and not with loose lips.