10 Of Ariana Grande's Best Fashion Looks (And 10 Of Her Boldest Ones)

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At 24 years old, Ariana Grande is one of this decade’s greatest fashion icons. Since her debut in 2008 where she played 13-year-old cheerleader Charlotte in 13 The Musical, she has been making fashion history. She has charted in the top 10 in 25 countries. That’s a record-breaking number! Her very first album entered the Billboard 200 and every album after that has followed suit. All three of Grande's full-length albums have been certified platinum by the RIAA. With a four-octave soprano vocal range and the whistle register, she has done things that no one since Mariah Carey could ever dream of doing. But it isn’t just musical achievements that have got millions falling all over her. There’s another reason that Ariana will always be one of the most followed Instagram stars.

In her lifetime, she has raised millions upon millions for charity: $500,000 in 2007 alone, before she became famous. She is a wonderful role model with a killer style. About 90% of the time, Ariana Grande is seen with her signature high ponytail, but we’re going to point out a few different looks here.

We have found ten of her best looks that will never get old or fail to cause our hearts to flutter, which is easy considering Ariana Grande cannot look bad even if she tried. So we’ve also gathered ten of her wildest outfits that range from overly sultry to eye-popping. From her most amazing to her craziest and back again, we alternate between Ariana Grande’s best outfits with her wildest ones.

Best: Never-Fail Red Dress

Let’s start things off by giving you one of the most flawless outfits that Ariana has ever worn. Pretty much every single female celebrity has worn a long red evening gown, but we think that Grande tops them all. This red dress from the 2016 Grammy Awards will go down in history as one of the best outfits to ever grace the red carpet. The Romona Keveza gown must have cost an arm and a leg, but it was so worth it!

There are a few reasons that this dress stands shoulders above the rest. For one, the buttons up the front give the bodice a corset look that is really unique. Plus, the buttons go all the way down her back and accentuate the way that the dress hugs her hips before flowing down onto the carpet in a bright red pool.

Bold: Not The Best For A Ski Trip

Where did Ariana Grande spend the holidays in 2017? With her family inside of a huge Colorado home that rents for $10,000 a night. Her family must have been ecstatic to learn where they would spend Christmas. Airbnb offered her and her family and friends a seven-bedroom mansion to use, and she took it. The mansion has its own movie theater, bowling alley, and private chef who cooks gourmet meals three times a day.

Whenever Ariana Grande updated her Instagram, all we could see was this outfit. It did steal away from her announcement. I mean, she does know that no one is going skiing in that coat or those boots, right? She looks great, but it’s insane that she’d wear ski goggles with that outfit. Plus, who can wear mustard, anyway? It’s kind of like Cher Horowitz took a time machine to 2017 without updating her wardrobe.

Best: Party Like A Grande

When Ariana Grande decided to partner with Lipsy London, we were thrilled. Lipsy London is a women’s clothing brand established in London in 1988 that specializes in celebrity fashion. Out of all of the outfits she wore for the promotion, this one caught our eye like no other. When asked about the collection, Grande said, “It's so great getting to collaborate with Lipsy to do something special for my fans. The line is youthful, affordable and I know my fans will love it."

The dresses from the collection are affordable, just as Grande said. They start at $50. The shirts and skirts are even cheaper. That in itself is exciting, but unfortunately, her collection is out of season. Hopefully, it will be back this spring! If not, we’ll just have to save this photo on our phones and stare at it every day, wishing we looked half as good as she did.

Bold: Her “Wildest” Look

Before we get into her really crazy and sultry looks, let’s take a look at her “wildest” outfit ever – the teddy onesie that she holds close to her heart. Anyone who knows Ariana knows that she loves animals to a fault at times. To make things worse, she literally has more than one of these. She prefers to wear her pink bear onesie with heels, but it seems this one is her favorite. She wore it at the Honeymoon Tour Meet & Greet in San Jose where she took photos with fans. Funnily enough, you can buy an identical one at Kigurimi Shop for under $70, so she might have been advertising a bit. But what adult is brave enough to wear an animal onesie in public? Perhaps there will be a few more now that Ariana has proven that it doesn’t have to make you look like a 9-year-old.

Best: Jessica Rabbit Meets Barbie

She looks amazing! Seen at the 2016 MTV Movie Awards in Burbank, Ariana Grande stole the whole show (and there were tons of huge celebs there). Despite her being dark-haired, she kind of gives that whole Gentlemen Prefer Blondes vibe, doesn’t she? After all, she did perform "Dangerous Woman" that very night in this silky pink gown with a furry shawl. The song is not very Marilyn Monroe, but definitely sultry much like the icon herself. And you don’t notice at first, but that diamond necklace makes her stand out ten times more!

There isn’t a time this "Put Your Hearts Up" singer has looked classier or more mature. Most of her mature looks involve black leather or showing off that body that she is so proud of. But this time, she takes a refreshing route.

Bold: She Doesn’t Do Winter Well

While she still looks cute, we’d say that this crazy dress is her worst choice ever. We’re not dissing her style, but we do need to bring this wild choice to light. Not everything she wears is for the spotlight, but as a celeb, it kind of is. That said, windbreakers should be left in the past and should not be turned into dresses. That’s like trying to turn Cheetos into a gourmet meal. This dress does make her waist look super slim, but it also makes her shoulders look like a 1980s businesswoman. And again with the ski goggles? Stop trying to make ski goggles happen, they’re never going to happen.

All around, we are pretty sure this is not the ideal outfit for skiing. Her boots have heels, which makes little sense, but with that dress/coat, we can’t complain about inappropriate shoes, can we?

Best: Bringing Reebok Back

Hiring Ariana Grande to be their model/spokesperson is the best thing that Reebok has ever done (this is one of her many Reebok looks). They could have gotten some large athlete to make their sweatshirts look fairly average like every other similar brand, but nope. They got Grande who looks like an '80s pop star who teaches a workout routine for incredible legs in six weeks or less! We mean that in the best way possible, because sometimes throwbacks are awesome. The leg warmers, off the shoulder sweater, and high ponytail (her signature) create one of her best looks. It’s so relaxed yet so fine.

The leg warmers and baggy shirt look is making a comeback. Part of that is due to Ariana Grande showing us that we can still rock the look.

Bold: Not So Ugly Duckling

If anyone else wore this, they would be called the ugly duckling and would never hear the end of it from friends. Ariana looks good in anything, but this is definitely one of the wildest things she’s worn. There’s no doubt that she wouldn’t be caught dead in the dress today. But when she was 18, she wore it to the Project Angel Food's 2011 Divine Design Gala at the Beverly Hilton. We can definitely give her a break for being 18 when she wore it. Teenagers do the craziest things to stand out, and Ariana Grande is no exception. The cut of the dress is all wrong and the feathers are way too much. Like we said, she still looks great, but she would have looked 100 times better in something else.

Best: Her Greatest Moment

Ariana Grande’s greatest moments were no doubt during her benefit concert for Manchester. When a tragic event ended her concert early, she felt so bad about the damage that had been done that she decided to make up for it with another concert. She was so selfless in the act as she wore an outfit that wouldn’t draw attention to her body. Average jeans that didn’t hug her shape and an oversized Love for Manchester shirt covered her body. The look is one that you can chill in at home, and she wore it to a concert. There’s nothing bad we can say about Ariana on this day. She raised two million dollars for the cause and cried more tears than we did while watching Up for the first time. While this isn’t a standout outfit, everything it stands for makes it rank as one of the best.

Bold: The Old Outback

Never wear dungarees (or what we call overalls in the States) unless they are the absolute perfect pair. And when you do wear them, don’t just wear a bralet underneath. Again, she looks good, but the dungarees add about twenty pounds and the lack of a shirt is alarming. If you think it’s bad, you should see the view from the back. To be fair, she was showing off her '60s look for the Hairspray Live! premiere, so I guess it did fit the occasion. She was Penny Pingleton, after all.

She’s about ready to go capture a lion or croc right now, so we wouldn’t mess with her. Unless of course, you’re the fashion police like us, and she has worn much better overalls than that. If we were her, we’d check out Kylie and Kendall Jenner’s line of clothing which includes knockout dungarees you can be proud of.

Best: Finally Growing Up

We’d say this was one of Ariana’s first appearances in public where she looked like she had moved past adolescence. She didn’t look like some Miley spin-off or some Marilyn Monroe wannabe. She was herself, and it was the first glimpse at who that really was. The legendary day is not one that will be forgotten, and neither is that legendary dress.

The moment happened at the 2014 Teen Choice Awards where Ariana Grande won Choice Female Artist of the Year as well as the Choice Single for the song "Problem" with Iggy Azalea. In our opinion, the white dress was one of the best things that the singer has worn. It was appropriate, safe, yet unique. It wasn’t what she would have worn for the Kids Choice Awards and it wasn’t what she could shine in at the red carpet. But it was perfect for the Teen Choice Awards where she balanced maturity and youth.

Bold: She’s A Dangerous Woman

It’s easy to see what happened here. Ariana was performing "Dangerous Woman" which is quite provocative, to say the least. Ariana can often make herself look classy where others would look trashy. But in this case, she leans toward trashy and we aren’t having it. We can take it since she rarely does this, and we feel pretty shocked seeing her like this. But the bodysuit under the sheer top covered in jewels is just so wild for her! She has claimed that she has no problem with showing off her body, but we all know she's not normally like this, so for her to get wild for this make us gape even though we can’t help but stare. The boots that Ariana would normally wear with a hoodie or short shorts look much wilder with the risqué choice of attire.

Best: School Girl Blues

It seems that Ariana always changes up her style when traveling to Japan and this is no exception. In Japan, the schoolgirl look is all the rage. After all, nearly every school has a uniform and most of them include plaid skirts and white stockings for girls.

In this outfit, Ariana was promoting her new album My Everything at DiverCity Tokyo Plaza. She made the perfect schoolgirl with her ponytail, knee-high stockings, plaid skirt, and grey crop top. She really knows how to appeal to her audience without losing who she is. The last time she was in Japan, she wore that pink animal onesie which is popular in Japan. She also wore double buns which is a go-to anime girl style. Many favor this look and we can see why. It’s youthful and it brings out the kid in her without taking away from her newfound maturity.

Bold: Is That Foil?

Our favorite thing about this is the hair. Do you know how hard it is to get white/silver hair without $500? Trust us, it’s nearly impossible. On Ariana, we don’t care how much she spent on it, it looks awesome on her and we are jealous. But we’re not here to talk about her hair, nor those pompom earrings. Okay, maybe the earrings – they are pretty insane.

It literally looks like Ariana Grande is wearing either aluminum foil or that glittery Christmas wrapping paper here. It is crazy, and not done very well. Remember when kids would dress up like aliens or robots in the '90s and early 2000a? That’s pretty much what this wild look seems to be. It is some childhood fantasy that Ariana is trying to fulfill where she becomes a futuristic space warrior princess from another planet.

Best: How To Wear Grommets

If you’ll look at women like Selena Gomez, Kendall Jenner, and Ariana Grande, you’ll realize that grommets are making a comeback. For a 2017 interview with Cosmopolitan, Ariana sported this leather two piece that screams confidence. The stars somehow work with the circles, and we want that skirt! If you want to add a feeling to the photo, just wait until you hear what she said during this interview. She wants us to feel strong, valued, and like we hold the world in our hands:

“A lot of times, women are labeled as a [jerk] or a diva for having a vision and being strong and using their voice, and it’s just not the case,” she says. “You can be strong and be friendly. [We] don’t have to be just one thing, you know?"

Bold: Stars In A Different Light

While the stars in the white leather gave us nothing to complain about, these stars are a little different. This was one of her many looks in her "Focus" video. While other looks in the video were good, this one is often made fun of for being too much, and that’s not hard to understand. While we don’t believe in bullying, there’s a reason that this look was turned into countless memes. There’s nothing wrong with it, but we didn’t say there was anything wrong with the other outfits in this list either. It’s just that the glow in the dark stars look like a 12-year-old boy’s bedroom. The boots are by far the best part, but the rest is just as wild as Madonna rampaging through a 2009 Lady Gaga concert. We don’t know if that ever happened, but we know that people would flock if it did. And we love both of those girls!

Best: Moschino

This full-on Moschino look could kill with one glance. Moschino is an Italian luxury fashion brand that has been one of the top designer brands for a long time. While this looks like a dress, it’s actually a top and skirt that Ariana wore at MTV VMAs in 2014. If you’re going to wear leather, you might as well do it right. This one is just on the edge of wild, but since it’s Moschino (who does leather with such passion) we couldn’t do it. It’s a bit wild, but not that wild. And it’s one of the best outfits she’s ever worn, so, we’re rolling with it. There are so many details that our heads might explode, but our love for it makes up for it. Where the amazing white leather outfit would be likened to your ideal chicken sandwich, this one is like a juicy steak that is cooked to perfection.

Bold: Wild Bunny On The Loose

This has become Ariana’s most iconic outfit of all time and is in the running for the most iconic outfit any celeb has ever worn. If you don’t believe us, show the silhouette to anyone and see if they can guess who it is. They surely won’t guess Justin Bieber.

Complete with fluffy tail, lace leggings, and heels, Ariana became a bunny for this Dangerous Woman photoshoot. She explains that this look is a lot more than some silly mask and women’s rights movement. It’s really her alter ego. "[The Super Bunny] is my superhero, or supervillain – whatever I’m feeling on the day," she explains. "Whenever I doubt myself or question choices I know in my gut are right – because other people are telling me other things – I’m like, ‘What would that bad Super Bunny do?’ She helps me call the shots."

Best: Back To Basics

We love how she channels her inner nature-loving Shaman/Druid hybrid here. The outfit was worn during her On Air with Ryan Seacrest interview talking about her Dangerous Woman album. She spoke about where the ideas came from and what the album means to her. At 22, she believed that she had recently become an adult and had made tons of changes in her life.

"The album is definitely the next step for me," she revealed during her appearance. "It still sounds like me, but it feels like a more mature, evolved version. There's a nice blend of the R&B vibes and a nice blend of pop vibes. The whole body of work is a little darker and sexier and more mature." Little did she know that her concerts would sell out and the album would top charts so quickly. And little did she know how adorable she looked that day!

Bold: Back To Middle School

Although the look was complete satire, we can’t leave it out. It is 100% the wildest that she’s ever gotten. We’re talking bubble gum, flamingos, and rainbow headbands on her Tonight Show skit known as Ew! In this skit, she plays Sara’s (Jimmy Fallon’s) best friend Alexa Armstrong. The skit is one of the show’s most popular and we can’t stop watching it. But that look, complete with unicorn purse, is the wildest thing that any 21-year-old has ever put on their body.

We applaud everything that Ariana has ever done on The Tonight Show with Jimmy Fallon as she really is a star. And those impressions were some of the greatest things our ears have ever heard. But this outfit takes things to a completely new level. Anyone can do sultry, but only Ariana could do a teen girl with a pound of gum in her mouth.