Ariana Grande's Killer Legs Couldn't Save These Awful Outfits

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Ariana Grande's net worth is much higher than you think, and her ever-evolving career path proves why. Since 2024, the "i wish i hated you" star has entered a major turning point. With her first major film role as Glinda in Jon M. Chu's "Wicked" and "Wicked: For Good," the pop star is proving she's much more than a Nickelodeon child star-turned-chart-topping musician. And while she was topping charts, touring the world, and winning countless awards, Grande's bold and often unconventional fashion choices also garnered significant attention. And, while it's mostly been positive, many of her looks have also sparked criticism and had people scratching their heads.

The artist has long been known to be fearless when it comes to experimenting with fashion. Although she has quite the petite figure, she's known for her striking proportions and long, lean legs. They're a feature of hers she likes to highlight by wearing fashion pieces that make them stand out best. But while some of the outfits that show off one of her best features have landed her on multiple best dressed lists, others have missed the mark entirely. 

In 2011, Ariana Grande attended the opening night of "Born Yesterday" on Broadway. While it's completely understandable that the occasion called for something elevated, this strapless midi dress did everything to work against her. The choppy hemline and heavy draping cut her petite frame at the most awkward points, and the style of the dress aged her. At the time, Grande was just 17 and her career revolved around projects for younger viewers, including Nickelodeon's "Victorious." Perhaps a cleaner cut outfit in a vibrant color would have better flattered her frame and felt more in step with her age and career at the time.

For a gala in 2011, Ariana Grande wore a dress that gave serious ostrich vibes thanks to the exaggerated feathered skirt. There's no denying the look was eye-catching, but the heavy volume of the skirt drowned her, and the fitted satin top didn't help her case much either. Not only did it fail to define her waist, but it also created a stiff, boxy shape that worked against her figure. Then, the contrast between the voluminous feather skirt and the heavily structured bodice made the outfit feel disharmonious, resulting in a costume-like outfit. 

For the 2016 Billboard Music Awards, Ariana Grande showed up in a heavily slit gown that felt so futuristic it was bordering on costume vibes. The electric blue graphic line detailing, sharp cutouts, and the bold blue velvety bungee cord-like lining gave the dress such a strong sci-fi feel that would've been perfect for the premiere night of a TRON franchise film. The busy design and the length worked against the "Wicked" star's petite figure. While the dress is bold in theory, we're not quite sure if even supermodels like Gigi Hadid could have pulled it off. 

Not only did Ariana Grande's LBD for Aretha Franklin's funeral feel a bit inappropriate for the solemn occasion, but the dress itself didn't do much for the pop star. The very short and slightly flared hemline hit at an awkward point of her legs and ended up visually shortening her best feature rather than elongating them. Honestly? This would've been the perfect LBD for the opening night of "Born Yesterday" in 2011. However, in a setting where understatement is paying respect, the silhouette was just too distracting. Perhaps a true fit and flare dress with a decent hemline would've been more ideal. 

For the Billboard's 13th Annual Women in Music Event, Ariana Grande wore a bubble dress by Christian Siriano and was styled by celebrity stylist, Law Roach. Roach selected a beautiful shade of lavender that complemented the singer's complexion perfectly. On the other hand, the exaggerated silhouette of the dress styled with thigh-high boots? Not so much. The two pieces may have worked independently in showing off Grande's killer legs, but together they overwhelmed her petite frame. The voluminous skirt detail adding unnecessary bulk and the addition of the tall boots created a bottom-heavy effect which is a big no-no for petite women.

For Ariana Grande's 2020 Grammys performance, she opted for a lingerie-inspired ensemble. While the concept fit the performance, the execution fell flat by doing too much. The corseted bodice, the feather trim detailing throughout, and the diamond-embellished emerald necklace and earrings were all vying for attention and created a cluttered look. It was another look that overwhelmed her petite figure and failed to bring out the best features of the singer. We would have loved to see Grande in a single, silk slip dress paired with studded diamond earrings, which would have allowed for the artist's performance to take the stage and not the costume-like outfit. 

It's admirable how much Ariana Grande, whose had a complete evolution, takes bold fashion risks. The Dior Haute Couture dress, or shall we say work of art, she wore to the 30th Critics Choice Awards certainly made a statement. The intricate structure, cascading fringe, and overall detailing are beyond impressive. With that said, this was one of those moments where the complexity of the design overshadowed the wearer. The "Wicked" star's presence isn't enhanced by the dress, and also blurred the clean leg line she's known for flaunting. Unfortunately, even her killer legs couldn't break through all of the visual noise of the haute couture art piece. 

If you've been a fan of Ariana Grande, you'd know she's a huge fan of bubble dresses. While some can look absolutely amazing on a petite figure like hers, her Givenchy dress for the 2025 VMAs leaned too far into volume. The exaggerated tulle skirt dominated her frame. It also evoked strikingly similar energy to the JW Anderson bubble-style dress she opted to wear during her October 2024 SNL appearance. On top of being often unflattering for her petite figure, bubble silhouettes, while fun and charming, can seem a bit too playful if revisited too often in your 30s and beyond. 

To promote "Wicked: For Good," Ariana Grande sat down for an interview with co-star Cynthia Erivo, who shares an emotional bond with the singer, for "The Oz Vlog" in November 2025. The pop star, who plays Glinda, wore a hot pink ensemble in a Pierre Cardin dress and Gianvito Rossi pumps. While the look photographed beautifully when she was sitting down, standing revealed a key issue: the dress was too long for the petite singer. The look would've felt much more intentional and flattering if her style team had the dress tailored to mirror where it landed on the runway model's legs.