In 2017, J. Cole opened his 4 Your Eyez Only tour by wading through a sea of fans in a full orange prison jumpsuit with “Property of” scribed on the back. It was one of the most memorable aspects of the tour that fit perfectly with his prison courtyard stage design, reflecting powerful themes throughout the album about incarceration. 

The mind behind this unforgettable moment and several others was designer Raeana Anaïs. The Brooklyn-born multi-hyphenate started working with Dreamville in 2017 after Felton Brown—the label’s VP of Creative Services and her longtime friend—reached out to Raeana to help design Cole’s stage outfit for the tour. While talking on the phone with Complex, Anaïs revealed that the rapper’s memorable prison jumpsuit was her first idea. Cole loved it, and she had to complete it in a week.

“I had this whole concept of maybe starting the tour with one type of jumpsuit, and then by the end of the tour maybe he’s in maximum security, maybe he’s in a straitjacket,” Anaïs explained. “It got super conceptual, and Cole was so receptive to it all. I didn’t think it was going to go anywhere. Then Felton hit me like, ‘He loves these. Can you fly to Los Angeles tomorrow?’ I wasn’t prepared for that at all, so I got prepared very quickly.”

raeana anais j cole's stylist profile
Image via Raeshon Roberson | Branded By Rae Productions

Raeana is Cole’s personal stylist and the Director of Design for Dreamville, responsible for not only styling him for tours, music videos, and other major events, but also leading the charge for the label’s apparel as it begins to incorporate premium pieces into its collection. The look would end up being a centerpiece of the tour that added a new layer of storytelling to Cole’s performance. From there, Anaïs officially joined the team and began working on the relaunch and rebrand of Dreamville apparel, focusing on trying to elevate the brand so that it is able to create bridges with consumers who may not even be familiar with the music label.

As for her approach to styling the multi-platinum artist, Anaïs understands that it’s all about balancing what Cole likes with new things she thinks he’d be willing to try. The key to J. Cole’s personal style is subtlty. He presents himself in a way that feels accessible while still being stylish. His looks resonate with his fanbase because they never feel too glamorous or out of reach, and as he rapped on a recent guest verse, “Please don’t get it fucked up from this homeless aesthetic.” Cole is still real-life wealthy and can throw in a sneaky flex whenever he wants, like when he wore sweatpants and Crocs to perform at the 2021 iHeartRadio Music Awards, but had on Gallery Dept. socks that retail for nearly $100. Anaïs explained how that look in particular was all Cole’s idea, and that she loves how he is already deeply rooted in his own established sense of style. 

“What’s so cool about him is that he has his own very defined personal style,” she said. “That’s very clear and concise, and to me, there’s a formula. So when I’m looking, I’m thinking about that formula, but I pretty much just look for things all the time.”

With Dreamville apparel’s Spring/Summer collection set to debut at the label’s second annual Dreamville Festival in Raleigh, North Carolina on April 2 and 3, Complex talked to Anaïs about expanding the brand beyond merch, how she solved the almost impossible task of making small jerseys fit Cole, and more stories behind some of J. Cole’s memorable fashion moments.