5 Ariana Grande Outfits That Completely Missed The Mark

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As a former child star, Ariana Grande got an early start to being in the public eye. With this constant attention, the singer and actor quickly learned to adapt and become a major player in the fashion game. From her iconic long ponytail and oversized sweatshirt look to her all-out transformative makeover for her role in "Wicked," Grande has a way of keeping fans happy with her styling choices. However, the "Eternal Sunshine" singer has had her fair share of outfits that missed the mark.

Granted, the early 2010s were not an ideal time to be a famous young person exploring fashion choices. In the era of jeggings, ballet flats, and low-rise denim, Grande did her best to defy the odds and wow us with her choices. But even thinking outside the box can come with its own limitations. The petite powerhouse has fumbled the fashion bag a handful of times during her rise to fame. From embellished babydoll dresses to a prom-style mishap to overalls that should have remained in the 20th century, here are some of Grande's worst looks through the years.

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While stepping out on the orange carpet for Nickelodeon's 23rd Annual Kids' Choice Awards in 2010, Ariana Grande accidentally committed several fashion crimes. First, the shoes in the above outfit simply don't match her dress, which is a mistake almost any teenager might make. However, the tan tone of the platform heels also doesn't match Grande's skin tone, making them really stand out for all the wrong reasons. Then, there's the questionable dress the "Sam & Cat" star is wearing.

One of the unfortunate trends of the 2010s was chunky, metal embellishments on almost every piece of clothing. Notably, this style was overly adopted by older women and several "Real Housewives" stars during this time, which might mean Grande was attempting to appear more mature by wearing this, but the plan backfired. The studs on the top of her dress don't fit the ethereal vibe of the rest of it, plus the bottom half of the dress appears just a bit see-through. Considering the Kids' Choice Awards coincided with the premiere of "Victorious" in 2010 and the debut of Grande's character Cat Valentine — and some of the sketchier things about Grande's time on Nickelodeon — it has us wondering who let the teenaged singer step out in this outfit.

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For those who remember it, the 2013 MTV Video Music Awards were an all-around hot mess express. There was Miley Cyrus's life-changing performance alongside Robin Thicke that had the internet in a tizzy for weeks. Justin Timberlake also performed a medley of songs for an extended performance before winning several awards. With all the chaos that occurred onstage, it would have been easy to forget almost anything else that happened at that year's show. Ariana Grande also wasn't nominated for any awards and didn't actually perform on the main stage for the tumultuous event, so many viewers probably missed her purple 1980s prom dress flop.

However, Grande did a pre-show red carpet serenade while other stars were arriving for the ceremony. Looking at the outfit she chose to wear, we would have wanted to hide on the sidelines as well. While performing "Baby I" on the red carpet, Grande sported a sparkling lilac dress with a drop waist and a shiny, satin-like skirt. Again, the color is not the best for Grande's skin tone, but the most egregious faux pas is the era the dress is reminiscent of. Bulky, flashy, and slightly frumpy, the outfit felt like a bad prom dress Josie Geller from "Never Been Kissed" would have worn unironically. Not Grande's most sleek and up-to-date fashion moment by far.

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During a press tour for "Hairspray Live!" Ariana Grande stepped out in quite the mishap of an ensemble. In yet another 'fit that's a throwback to an unfortunate era, the pair of billowing black overalls above is reminiscent of when JNCO jeans reigned supreme on the playground. This style of oversized, triangular denim was pervasive throughout not just the '90s but was also a main staple of hip-hop culture. So, it makes sense that the singer adopted such a wild style during the portion of Grande's dating history where she was bouncing from rapper to rapper.

After Grande and rising rap star Mac Miller collaborated on her single "The Way" in 2013, the two became a couple in 2016 — the year that Grande donned this outfit. Perhaps it was Miller's influence that led to Grande making such a bold fashion mistake. Even if his musical prowess helped her climb up the charts, the same can't be said for the late performer's sense of fashion. The two eventually split in 2018 but remained close friends, with Grande even paying tribute to Miller after his death.

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Before the world shut down due to the COVID-19 pandemic in 2020, Ariana Grande was able to perform at the Grammy Awards. Unfortunately, the outfit she chose to dazzle the audience ended up being more of a dud. Grande was one of the main performers of the evening, singing several songs from her "Thank U, Next" album and a cover of "My Favorite Things." However, one of our least favorite things from this performance was the outfit the star chose to wear.

Starting the performance in a gorgeous black gown, Grande did a quick costume change to segue into "7 Rings," and the look was a snooze. Attempting to match her backup dancers in cream-colored lingerie, Grande ended up donning something that was more "Christmas sleepover" and less "sultry single lady." Plus, the knee pads ended up looking more like bandages than part of a cohesive outfit. Considering how Grande loves to spend her millions by treating her friends, hopefully one of her pals will be able to pay it forward and give her some fashion advice next time she's invited to entertain the Grammys crowd.

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After a few years of crushing it fashion-wise, Ariana Grande once again slipped up while attending the 82nd Annual Golden Globe Awards in 2025. Wearing a vintage Givenchy dress that had never been worn before, Grande displayed why it should have stayed in storage. Making the list of the absolutely worst dressed celebrities for the awards ceremony, Grande kept posing with her gloved hands drawing attention to her stomach. This displayed what was inherently wrong with the dress: a waistline that did not compliment Grande's notoriously tiny frame and that created the illusion of a baby bump. Once again, she also opted for a color that washed out her complexion.

What's surprising about this unfortunate choice is that for the entire press tour for "Wicked," the film Grande was attending the awards to represent, she played with wonderful outfits that embodied her character, Glinda. After seeing the star in puffy pink princessy dresses, having her arrive on the red carpet looking like a sad extra from "Pride and Prejudice" had many people scratching their heads. Luckily, there will be plenty more awards ceremonies to attend where Grande can once again claim her spot as a leading lady with impeccable fashion sense.