Missy Elliott is one of the best-selling female rappers in history with an illustrious decade-spanning career, but this summer, she’s doing something brand new: Embarking on her first-ever headline tour.

“I was so in my writing and producing bag, that I always put that first,” Elliott recently told Vanity Fair. “ I just woke up one day and I called Mona Scott-Young [Elliott’s manager] and said, I’m ready to go out!”

The Out of This World Tour, with its 30 dates across the country, reunites the Grammy Award winner with her longtime peers and collaborators, Busta Rhymes and Ciara, with special guest Timbaland. Ironically, the tour coincides with the 25th anniversary of Elliott’s sophomore album, Da Real World, which included hit singles “She’s a Bitch”, “All n My Grill”, and “Hot Boyz.”

Released on June 22, 1999, Da Real World solidified her place in music history, a continuation of Elliott’s brand of Afrofuturistic music. “I had my mother playing church music and my daddy playing Marvin Gaye at the same time. So vocally wise it was a blend of both that I ended up having. Then, when I got with [Timbaland], he didn’t really realize the gift that he had, but I always just thought he was a genius. We were in high school, I met him through Magoo, and I went over to his house and just started singing over stuff that he had and his little Casio keyboard. But it wasn’t just the regular sound, the fact that he was taking animal sounds and making music out of sounds, I think that contributed to a whole other thing for us. So we ended up just doing our own style of music, and that’s how you got the different cadence sound. I wasn’t a singer able to sing a bunch of runs, so I was doing a lot of rap-singing, which people weren’t really into then. So all of that came from that period of when I was in high school, of us having a different sound. But we didn’t know it at the time,” Elliott reflected.

For the tour, Elliott also collaborated with creative director and stylist June Ambrose, who famously outfitted the artist with the unforgettable inflatable suit she wore in “The Rain (Supa Dupa Fly)” music video in 1997.

“When I first met June, she said, ‘darling, no one’s ironing their pants anymore.’ Because I came from Virginia and I wanted everything creased and T-shirts starched. She said, ‘darling, no one’s doing that anymore. You want to be matchy-matchy?’ June taught me about fashion very early on,” Elliott said.

The duo has worked together for the majority of Elliott’s music videos, creating looks inspired by the musician's thought-provoking lyrics. “The lyrical content is so provocative, but the images that we created were such a dichotomy for what women in hip-hop, at the time, was delivering. So Missy didn’t feel the need to match that with overtly provocative clothing. Because all of the sex was really, if not in the lyrics, it was also in her body movements and her dance and the fact that we didn’t lean into that and we were disruptive in the conversation where I was, like, we’re redefining sexuality and how we’re perceived as women.

Culturally, I think that is really liberating. There were tons of artists that came before us that stood on their center, like Queen Latifah and MC Lyte and those girls who didn’t feel the need to necessarily play into that narrative, but Missy specifically, because her lyrical content was so sexual and…about the things that you would always speak about privately or behind closed doors. And then you look at her and she’s, like, this super sporty, fun, superhero, tomboy. To me, that’s really where I think we carved out our own space, and I’m always going to say ‘we’ because everything is mute without a muse like Missy. And no matter what, whether it was the director or choreographer or the costume design, Missy really brought it all to life—she's what made it so believable. She’s so authentically magnetic and connects with the looks,” Ambrose said.

When preparing for the Out of This World Tour, Ambrose’s process began with storyboarding and “then going into the technical aspects of what is needed for performance, and then going into lighting, and then going into what those screens are looking at, and then thinking about what it’s going to look like up in the nosebleed sections,” she said.

Elliott takes a moment to point out that Ambrose’s thoughtful approach sets her apart from other creatives in her field. “It just shows you that she’s not just thinking about some fly clothes, like, just hearing her say, ‘I’m thinking about the people in the nosebleed.’”

Ambrose began doing costume design for Elliott and many other artists at a time in the ’90s when major fashion houses weren’t opening the “floodgates” and loaning clothes to hip-hop artists. From there, Ambrose tapped into her own creativity and looked to the message within Elliott’s lyrics to put together looks that would serve as an indelible image and style that defined a generation.

For the final looks, Ambrose didn’t stray away from Elliott’s signature style of mixing sportswear and luxury. “It’s like this June-iverse-meets-Missy’s-world kind of energy. We’re redefining like we did back then, 20 something years ago, athletic wear, sportswear silhouettes, and reimagining it in this world that feels very tangible, but it still makes you imagine enough with whether it’s the color play or the textures and all of the beautiful, cinematic artwork that’s being done to immerse the audience into this world,” Ambrose shared. “I think the combination of all of it is going to be really magical. It doesn’t happen in one singular person. I think collectively from the technical team to choreography and Missy leading the charge and being very clear about what she would like to see. We’re able to deliver based on that.”

As they enter the next phase of their partnership with this summer’s tour, Elliott and Ambrose reflect on their past work together: They both agree that their favorite project thus far is the 1999 music video for “She’s a Bitch.” “I look back at that video and, even to this day, it’s still so far ahead, it’s still nothing like it. It’s so rock and roll, it’s so everything. We always had a [sense of] fearlessness,” Missy said.