Ariana Grande Outfits That Totally Missed The Mark

The truth is, when it comes to her outfits, Ariana Grande often gets it right. In fact, we'd go as far as to say that she's a star who defined a generation when it came to her iconic look, as she was arguably one of the main driving forces behind the super oversized trend we saw everywhere thanks to her super baggy sweatshirts, which resulted in oversized sweaters becoming massive (literally). But even as one of the most stylish stars on the planet, she's not immune to the odd fashion faux pas or two, and she does have a handful of outfits over the years that have missed the mark.

In fact, Grande — who penned a very important message about comments on her body — has admitted that she sometimes struggles to look back on her older looks because her style has changed so drastically since then. "My style has changed so much over time for the better. I look at old pictures even from a few months ago and I get sick to my stomach, it's just so embarrassing," she admitted to Cosmopolitan (via Female First) in 2014. The star didn't explicitly confirm which outfits she regretted, though we can certainly vouch for her changing her style.

Today, Ariana Grande is known for having a lot of fun with her fashion, but back in 2010, she attended the premiere of the movie "Shrek Forever After" in an outfit that really missed the mark. A premiere of a children's film is a time to have fun with fashion and maybe even bring some bright colors or embellishments to the red carpet. But Grande went the opposite way with her look and dressed more like she was heading to a sleek, evening event than a fun night with a green ogre.

The star was only 16 years old at the time, but her slinky all-black mini dress looked like it was designed for someone much older. She paired the bodycon look with purple and black stilettos, which, again, looked as though they were made for someone much older than the teen. Not only that, but the former "Victorious" star even painted her nails black to match. While black nails can look totally chic when done right, this whole super dark look just didn't work in the context of the event.

In 2011, Ariana Grande made an appearance at the iconic Planet Hollywood in Times Square, New York, where she left a lasting legacy by creating a handprint for display. But we were more distracted by her odd choice of tights. The star, who was just 18 years old at the time, opted for thick nude tights (or pantyhose, if you will) with chunky light brown pumps. We get that maybe she wasn't all that comfortable showing off her legs, which, of course, is her prerogative. The only issue here is that the super thick hosiery with a slight sheen really aged the teen and made the whole look a little dowdy. The hosiery didn't suit the open-toed shoes either, as the best way to do an open-toe with tights is to rock a bright color rather than something too similar to your skin tone.

This one's a real shame seeing as her cute white dress and the platform heels would've looked totally adorable without the stockings, as both were appropriate for the event and on-trend for the time. What we will say though is that we know Grande was still trying to find her style around this time (heck, who isn't at 18?) and it's missteps like this that help us to find out what looks good and what works for us.

Now, don't get us wrong, the lace crop top and high-waisted baggy pants Ariana Grande wore on the red carpet at the 2016 MTV Video Music Awards didn't make for a horrendous outfit. The look itself was very in, keeping with Grande's style and the matching two-piece look was pretty chic as a whole. Our issue falls with the length and bagginess of the pants, which just didn't work. At all.

We know, Grande was the queen of everything baggy around this time, but her super loose-fitting bottoms, even though we're sure they're supposed to be that way, actually look more like she fell victim to poor tailoring. The ill-fitting pants swallowed up her bottom half and looked a little messy at the ends as they covered her shoes, which is a major shame as we usually love to see the stylish footwear the "Into You" hitmaker is rocking. The pants were so long on her 5-foot frame that they literally reached the floor, causing a serious tripping hazard (which isn't great when you've got to walk down a red carpet with plenty of paps snapping your every move).

For similar reasons to her MTV VMA look above, we weren't really feeling Ariana Grande's overalls, which she sported to attend the premiere of "Hairspray Live" in 2016. Of course, Grande can pull off pretty much anything, so we're not surprised she gave the denim overalls a go. Only, they'd have been more appropriate at something like a soundcheck or even a daytime talk show appearance. The dark denim look was super baggy too, which overwhelmed her petite frame. And, once again, the bottom of the outfit was left super long and skimmed the carpet, giving this star another chance to fall over in front of the world. Thankfully, she didn't (as far as we know).

Another reason we think this black bra top and slouchy overalls missed the mark is because it was such a missed opportunity. Grande's look gave the vibe that she didn't want to overshadow anyone with her star power on the red carpet, but she was one of the stars of the show. She appeared as Penny Pingleton in the live televised production, so she had every reason to dress up for the occasion and make her mark on the red carpet. One thing that did still look great though was her classic voluminous ponytail, and we have a few tips on how you can do it at home.

Ariana Grande is almost as famous for her chic, feminine performance outfits as she is for her incredible voice, which is why her super casual, oversized on-stage look from 2018 surprised us. Grande sported this super baggy sweatshirt and jeans ensemble during her "The Sweetener Sessions" gig in Chicago. The look was a far cry from the more fitted, glamorous, and glittery ensembles we saw from her "Sweetener" era, and even though the event was supposed to be more intimate for her biggest fans, it wasn't exactly the kind of Grande-esque ensemble we're guessing fans were expecting. After all, if you were heading to an Ariana Grande gig, wouldn't you be expecting more of a statement outfit than a baggy sweatshirt, jeans, and boots?

At least this time though, Grande's long pants weren't an issue. She was ahead of her time with turned-up jeans, as cuffed jeans saw a massive resurgence in popularity in 2024. So, even though she doesn't always get it right, we can't say she's not still a trendsetter.