Five Fits With: Rapper, Producer, and Incredibly Cool Dresser Oddisee

Listen: I love rap music in all its forms, and especially some of its most mindless and violent offerings by way of the mumble and trap varieties, but I also love what people call “conscious” hip-hop when it’s done right. Sometimes, it can be preachy and boring, but in the case of Oddisee’s music, it is anything but. I would resist giving Oddisee—or any artist, for that matter—a genre label, as he is a true lyricist and songwriter, striving for economy and utility in tandem with artistry, rather than creating within the confines of a specific genre’s tropes. His live music on tour is just that: an actual show that doesn’t repeat nightly. He’s currently on his North American tour through December 18, and his new album, “To What End” is available January 20, 2023. (Tickets and pre-order are available here.)

Naturally, as an artist, he also happens to have fresh style to match. Below, Oddisee and I get into making music for over 20 years, the enduring influence of Marvin Gaye, the synchronicity between music style and fashion sense, shopping in Scandinavia for clothing that fits tall folks, how success brought him to buy less and more expensively, his formula for a properly entertaining live show, and plenty of other topics.

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

You’ve been making music for 20 plus years, right? I’m not a fan of genre tags and boiling music down to phrases, but your music is certainly more conscious and philosophical than a lot of rap on the top charts currently. How have you stayed prolific and inspired through all these phases of your life?

Just by living. Every day you have new experiences, and even older experiences, you perceive them differently. Being objective and stepping outside of myself and looking at my own existence gives me so much subject matter. It makes me want to try something new every day just because I’m alive. I have four walls and I make music here, but I made music here as a single man, and I made music here as a married man, and I made music here as a father of one and now a father of two. It’s the same room but multiple experiences, and those every day present new challenges and new forms of inspiration. So I think just leaving myself available to experience and always consciously looking to reinterpret that experience.

What do you appreciate in a good hip hop track that isn’t made by you?

I appreciate attention to detail the most, from the mix to the word play to the drum pattern. I like when there’s subtle details that it takes you some time to really capture, and every time you listen to it, you feel like you hear something new. A lot of rap tends to focus on beats and rhymes as separate entities, and once you go down that lane… You can really love a rapper and really love a producer, but the combination doesn’t necessarily make the greatest song.

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

I’d imagine your taste in style might be linked to some of your musical influences. What are some of your stylistic influences musically, or in terms of fashion?

Funny enough, my influences in music and in fashion both stem from the same thing—an appreciation for design, specifically. I love furniture design. I like the idea of things being aesthetically pleasing to the eye, yet highly functional. I want my music to be both entertaining and educational. With clothing, I like it to be aesthetically pleasing, but practical, so I’m big on dressing for the temperature and dressing for the weather. I never sacrifice in the name of fashion. I follow that same ethos in my music. I don’t like to add a lot of unnecessary things to my records like features for of some famous person just to get attention, or as a producer, an excessive amount of instrumentation. I go through this period of reduction to see what I absolutely need and what I can discard. But the end result is beautiful.

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

So it’s an amalgamation of all the stuff you’ve seen, but do you have specific influences?

One of my favorite artists of all time is Marvin Gaye. He mastered the art of education and entertainment where one didn’t necessarily give way to the other. You could listen to one of his songs at a cookout and dance to it, but if you listen to that same song alone in solitude, you hear the message. I want my music to be able to do that. I don’t want it to just be sheerly educational and preachy, but I don’t want it to be completely brainless at the same time, so I lean a lot on the musicality to be enjoying and moving, and the lyrics to be thought-provoking. I don’t know if it’s intentional, but I look to the style of artists from the late ’50s, ’60s, and ’70s. They had an effortless cool to them. It didn’t come across as though they were trying really hard to be fly. I come from the underground school of hip-hop, and initially, in the beginning of my career, it was shunned to focus on your aesthetic. It had to be about the music to get respect and recognition, and you wanted the music to speak for itself. It came later that the artist became a brand, and there was such an importance on the artist’s opinion and appearance. I looked at artists whose appearance just seemed effortless and you could get a sense of what the music was about based on their appearance. I’ve always wanted to capture that. It’s been harder to do as the years have gone by, especially in rap.

I often hear that I don’t dress like a rapper. I love that. It’s like, “What does that even mean anymore?” Definitely in the beginning of my career, I looked like my music. And I think in the beginning of my career I looked like my music, but now my music sounds like me. It switched, and it always does. I go through different moods musically, and I go through different moods in fashion. Sometimes I’m all about heritage wear, sometimes I’m all about workwear, sometimes I’m all about minimalism. That’s definitely reflected throughout my career and my catalog. Mostly you can see it in my artwork where I’m at musically and where I’m at fashion wise. I try to tie them all together. If I’m in a minimalist zone where I’m selling everything and getting rid of everything, and I just want to simplify, my music sounds like it.

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

Are there any brands you’re particularly into at the moment?

I’m really into Kapital right now. I love a lot of the stuff that they’re doing because they play around with so many other styles of clothing that I like. They play around with workwear, they play around with vintage, they play around with modern cuts. So I feel like I’m free to get a couple small pieces from Kapital that are really diverse. That’s what I want in my music as well: for it to fit in a lot of different settings, and I feel like I can do that with a lot of Kapital’s clothing. But more than a brand, I think I’m really into wider silhouettes that come from Japan. I like a lot of Japanese brands in general, and Orslow. I visited Sweden earlier in my career and fell in love with a lot of the designers that a lot of the stores were selling there. People up there are a lot taller, and that’s when I really started to discover my fashion sense, once I found things that I felt fit my silhouette. For years I was shopping outside of my silhouette. Our Legacy fits me great. Love their stuff. Visvim fits me well.

You touched on it in the last question, but what are some of your favorite stores to hit when you’re on tour abroad?

I star a lot of places. Clutch Cafe in the UK. I like Brut Archives in Paris. Fortela in Milan. Our Legacy in Stockholm. And in New York, I love No Man Walks Alone.

Did your shopping habits change as you became more successful?

Definitely. The more I was able to make a good living with music, my pieces definitely got more expensive, but I bought fewer things. In wanting to dress my age, I bought more pieces that were classic. Whenever I knew I was going on a tour, which is every year, I’d buy new ‘fits to wear on that tour. I’d say it’s like every two or three years now where I’ll do a complete wardrobe change for tour.

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

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Christopher Fenimore

You’re about to go on tour and I was just listening to your live album Beneath the Surface, which I think is excellent. What makes for a good live show, and what will the shows on this tour consist of?

I think a good live show goes through moods and emotions. It starts off someplace and it tells a story that has a beginning, a middle, and an end. I love when artists do that, and that’s what I strive to do when I’m on stage. The initial first few songs gradually introduce you into the show, then it hits this high point, and then a gradual decline in energy. Right at the end, around the encore area, it jumps back up so that no matter how many peaks and valleys you go through during the set, it leaves on a very high-energy note. People tend to remember the beginning when they walk in, the first few songs, and the end, so I leave the energy for the beginning and the end. I love shows that are engaging with the audience. In my set, we curate specific moments where we’re just going to have room for improv. It may be talking to the crowd or bringing someone up on stage. We often have full out conversations on stage with the band as if no one’s there, like it’s just us. We find that audiences tend to love that because it lets them see a bit of our personality; it’s really engaging. We’ve heard that no matter how big the audience is, our shows seem intimate. We strive to make everyone feel like they’re having an intimate experience no matter how big the venue is. I think that’s what you’ll see on this tour as well: musicians who love to perform, love interacting with the crowd and love making them feel like they’re a part of the show.

You’re also about to drop a new album come January. How does your new album differ from your catalog thus far?

This new album was definitely the hardest record for me to make in my career. It’s why I kept having to push it back. It took a lot of time. I’m in a completely different head space on this record, and that head space was one where I was just lost. I got used to the catch and release of my previous records, meaning I would make a record within three months. I was on the road from the time that that record was turned in and manufactured, and I’d engage an audience and hear how they perceived a record. Then I’d take that data and go back home and put that into the next record, and then keep it moving. [That process] was completely taken away from me. For the first time, too much time ended up being a curse—a lot of overthinking, a lot of paralysis through analysis. I got in my own way a lot on this record. And for however many months that turned into years of me getting in my own way, it took that same amount of time to get out of my way to complete the record. I’m a lot more personal on this record. A lot of my previous records, I tended to ask questions without giving my opinion. This record, I’m giving my opinion a lot more, and that’s a first. This one differs a lot because I’m posing questions. I know I traditionally do, but I’m giving my own two cents on it as well.

Christopher Fenimore is a writer and photographer living in New York. Working with clients ranging from clothiers to vineyards, he’s also covered street style for a number of outlets. Follow him on Instagram at @c.fenimore.

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