Undoubtedly, 2024 has been a pivotal year for Doechii, the Florida-based rapper who has captured the public's attention with her unique blend of talent and style. With a mixtape endorsed by none other than Kendrick Lamar, titled "Alligator Bites Never Heal," Doechii has made waves in the music industry. Her collaborations with Tyler, the Creator and Katy Perry have further amplified her presence, and her performances have become the talk of the town. However, Doechii's influence extends beyond music, as her fashion choices have become an integral part of her identity. From her solo tours to appearances at Tyler, the Creator's Camp Flognaw festival, and her viral performances on "The Late Show with Stephen Colbert" and NPR's Tiny Desk concert series, her style has consistently been a focal point. Over recent months, Doechii has taken her fashion game to new heights, working closely with stylist Sam Woolf to craft a preppy, androgynous look that features vintage Saint Laurent suits, Miu Miu miniskirts, and a plethora of Thom Browne pieces. David Jaelin captures Doechii's on-stage presence in Miu Miu.

"Doechii is incredibly creative," Woolf shares with Harper's Bazaar. "She has a clear vision and knows exactly what she wants, but she's always open to collaboration. I'll present an idea, and she'll let me know if it aligns with her vision. Over the past few months, we've developed this aesthetic and mood board, constantly exchanging ideas to create this preppy office siren world."

Woolf delves into the inspiration and intentions behind some of Doechii's most iconic looks of the year. Much of Doechii's current momentum can be traced back to the release of her mixtape, "Alligator Bites Never Heal." Woolf explains how they conceptualized the look to complement the music: "It wasn't about specific people for us. It was more about seeing a shoe and her saying, 'I want to do something with this,' or it being a silhouette or an A-line skirt. It's very basic elements. It's a lot about textures, patterns, and colors. For her mixtape shoot, she told me she wanted the colors to be incredibly rich yet still hip-hop. The background on her album cover is this deep forest green that gives off a really rich, warm feeling, and she'd say, 'My clothes need to reflect that.'" David Jaelin captures Doechii in Gucci and Adidas for her appearance on "The Late Show with Stephen Colbert."

One of Doechii's most memorable looks this year was her performance on "The Late Show with Stephen Colbert." Woolf shares the story behind that look: "She came to me and said, 'I want to create three Doechiis and have us all look alike, linking our hair with our braids.' It all stems from within her, and she mentioned how she wanted to interpret hip-hop in her own way. She wanted that '90s nostalgia feel, but also incorporating preppy elements and wanting it to be refined. She choreographed the entire performance herself. The braids were her idea, and she and her hair artist executed that. We didn't specifically discuss brands when planning the look; it's always more about the feeling with her. That's the big consistent element for her: She wants to consider how her work will impact someone."

It's interesting to note the absence of specific brand mentions, as the final look, featuring Gucci prints and Adidas sneakers, screams hip-hop. Woolf recalls, "We tried so many different shoes! We tried heels, we tried loafers, we tried other sneakers, but it was just cooler to do the Adidas. If you know the history behind things, Adidas and Gucci have had collaborations in the past and also individually had such a '90s presence. People who understand that can pick up on those things, and that's what made that moment so cool." David Jaelin captures Doechii in Willy Chavarria for NPR's Tiny Desk.

Another standout look was the Willy Chavarria ensemble for her NPR Tiny Desk performance. Woolf explains why this look was perfect for Tiny Desk, which is always a significant moment for any musician: "We attended the fashion show in September in New York for Willy, and she wore a completely out-of-the-box Willy look—it was underwear with no shoes and socks. I was sitting next to her at the show, and throughout the event, she would say, 'I would wear that, I would wear that, I love that.' And that's rare because she's hard to predict! After that, I was trying to find the right moment for her to wear Willy. For Tiny Desk, she said it needed to look stylish but also needed to be somewhat sophisticated, relaxed, and preppy, and that's what the look encapsulated."

The idea of prep is a true constant throughout everything Doechii and Woolf do together, which is not something you often see from many women in music, hip-hop or otherwise. Woolf notes, "I think it's interesting as well for a rap girl to be doing that because you don't often see that—it's unexpected. You often expect a rap girl to be super sexy and overtly out there, and don't get me wrong, we've done many sexy looks! But she's also down to lean into the masculine energy. She's not afraid to show skin, and she's also not afraid to be covered up. The preppy thing was something that no other female was really doing. It also matched the mixtape's vibe—that was such a thought-out project and it didn't make sense to be so sexy for it." David Jaelin captures Doechii in Thom Browne.

Thom Browne has been a mainstay in Doechii's wardrobe, from Camp Flognaw to the recent VMAs. Woolf explains why they have returned to Thom Browne time and time again: "The preppy nature of it all, of course, brings us back to Thom Browne, but it's also the beautiful tailoring, the silhouettes, the colors, the fact that it can be feminine, it can be masculine. Also, it's really great to work with someone who has supported you from early on, who doesn't just come on board when you have a moment. I think it was at the CFDA ribbon cutting where she told me, 'This is me. This is what I want to do.'"

One of their next big moments is the 2025 Grammys. While Woolf can't share many details, he hints at what they have been planning: "I have a few houses sketching for us, and we're waiting to see the sketches. A lot of people want to dress her, especially after Colbert and Tiny Desk. I love it because she really is it. She can sing, she can rap, she can dance, she can act, she can be in fashion—she is so talented. The Grammys for her will be a big moment, and all we can say is we're not doing it over the top." David Jaelin captures Sam Woolf and Doechii together outside the Willy Chavarria show at New York Fashion Week.

Looking ahead to 2025, Woolf reflects on how he and Doechii want to evolve in terms of fashion: "I think it's always just about interpreting it in a way that no one else would do. Doechii pushes me. She'll say, 'Well, everyone would do that, so what else can we do?' We're always looking at runway looks that can inspire larger ideas, whether it's a photoshoot or a whole rollout. No matter what, we're going to keep pushing the envelope." This interview has been edited and condensed for clarity.