Jesse Boykins III Shares How His ‘Vintage Bedroom’ Style Plays Into His Music

“I look at myself as an expressionist, like a surrealist artist,” says Jesse Boykins III. The alternative R&B singer – whose sound stretches from classic soul to the accented, off-center elements of electronic – is known for his unique exploration of where music and fashion intersect.

“I explore a lot of different sounds and soundscapes and I try to explore a lot of different ways of communicating my emotions,” he notes. “I went to school for jazz, so I explore a lot of different genres of music — I’m open to hybridizing and blending things, mixing and matching elements together, and making things that might not seem like they’re going to make sense, make sense.”

Born in Chicago, Boykins spent part of his childhood surrounded by his fly-as-hell uncles while living in Jamaica, which ultimately shaped his perception of clothing. At first, the artist, director, music producer, and clothing designer tried to tone it down when returning to the U.S., but he eventually found his footing by expressing himself in whatever way felt best.

“I’m very big on curating things and trying to bring comfort to things that might normally feel uncomfortable,” he continues, speaking on his aesthetic. “I think that’s something that’s needed right now — people being okay with finding comfort in discomfort. That’s what I lean into in my art.”

Today, Boykins sets the tone in how he dresses the same way he does with his music — with unapologetic flair. After a run of new singles – including the recent “Go With The Feeling” – Boykins is set to drop a full-length album, New Growth, next month.

We hit up Boykins to talk about his curated sense of style and how he showcases that in his music and live performances, the kind of pieces he likes to collect, his personal perception of the world’s view on style and fashion, and more.

You have a very curated sense of style. What’s your personal style philosophy?

I like how things feel, so I usually start with feeling. I want to feel down to textures and different fabrics. I really love wool and cashmere, and I really love tweed. I try to get things along the lines of things that I connect with as far as that’s concerned. And then some people tell me I dress like either I’m homeless or I’m a millionaire. I take that as a compliment, I call it “vintage bedroom.”

That’s my speed right there. Like I just got out of bed, but I could go to the Met Gala.

I feel like that’s starting to become more popular too on the red carpet and especially with younger generations. They’re all about the comfortability, but also making it stylish.

That’s always been a part of my expression is to make sure of that. They say beauty is pain, I don’t agree. That’s not really my thing. I feel like you just want to be peaceful, as peaceful as you can make it. So that’s what I try to do in my style, try to make sure that I feel good, I’m at peace with what I’m wearing.

When did you first become interested in fashion and style and how have you connected it over the years with your music?

I think I was like five years old. I grew up in Jamaica, and my uncles are all pretty stylish dudes and were in a reggae band. My father was also a very stylish person who had the Gucci glasses with the safari hats, the 13 gold chains, the three gold teeth, and tried different patterns and stuff. So I was around it really early on and I used to dress like them.

When I moved to the states, I had to kind of change a little bit because I had to conform because of where I was living. I wasn’t trying to look like fresh meat out here so I adapted. And then when I moved to New York for college, I went back to my childhood in a sense where I felt free to express myself in whatever which way I could because New York is the scene that sense.

Have you have you connected that to your career in music?

Fashion has pretty much has been part of my life for a long time. And I think that aspect of exploration, trying new things, and learning the history of certain things is also a practice I have in my music. I explore a lot of different sounds and soundscapes and I try to explore a lot of different ways of communicating my emotions. I went to school for jazz, so I explore a lot of different genres of music. I’m open to hybridizing and blending things, mixing and matching elements together, and making things that might not seem like they’re going to make sense, make sense, so they kind of are parallels for me. I try to practice that as much as I can.

A lot of times when I’m making the music, I see what it looks like before it’s even finished and that’s down to what I’m wearing, what it smells like, where are we at, what the environment is like. I’m very big on curating things and trying to bring comfort to things that might normally feel uncomfortable. And I think that’s something that’s needed right now. People are okay with finding comfort in discomfort, and that’s what I lean into in my art.

How do you determine how you style your outfits for your live performances?

Oh, that’s easy. That’s based on movement. I do a lot of movement on stage, so a lot of times I’m trying to find things that can flow with me, that add another depth or another layer to my expression. I also layer a lot on stage. So in a sense, I’m “molding,” taking off molds and molds of me while I’m performing, and I think that adds to the storyline and makes the experience more memorable. Like,”Aw, man, he had an outfit on in this song and he took the jacket off and then he had this crazy shirt under the jacket, and then took the shirt off, had this skin-tight snakeskin.”

I like that aspect of it too. I try to make everything feel synthetic — so I try to make that as memorable as possible.

So who would you say are some of your style icons over the years?

Vivienne Westwood. Anything having to do with ’70s rocker energy. So Peter Tosh, Jimmy Cliff, Bob Marley, that aspect of them being so resourceful with what they had and still making it so flavorful and impacting so many different cultures of people. I also love Jean Paul Gaultier as a costume designer specifically. The Fifth Element, I love the styling and the costume design in that film. Also, the first Blade Runner. The styling on that and the costume design on that movie were very good.

Would you say when you’re out shopping, do you find yourself more going to new clothes or it kind of sounds like with some of these style icons and the mood that you just stated, it could be a little bit more vintage, like thrifting?

Yeah, to me I have no real formula for that. I think a lot of the newer designs are templates of older things that I would rather get the best quality of. That’s always my goal is to get the best quality. I actually design clothes as well, and so I might see a template I like, but I might not like the fabric, or the waistline cut, or I might want to shift it and change it to something else. So I do a lot of customization stuff too.

The seamstresses and the designs I work with, for me it’s just constant aspirations for the best quality. That can be vintage, or should I find a Guess original, it doesn’t matter. To me, it’s like just my eyes, what I’m paying attention to, what speaks to me.

Tell me a little bit about the most recent projects that you recently designed and are currently working on.

I designed my merchandising and stuff for my other album. I’m doing that now for my new album, but I’m also doing a capsule collection in conjunction with my album. And so my album cover is one of the designs I did with one of the partnering designs I work with. So it’s a one-on-one outfit, and we’re doing a couple of looks to embody what the clothing of the album looks like as far as fabric, cuts, and textures. It’s highly inspired by West African, Senegalese slash Japanese cut, and then some futurism in there. I sought inspiration from Jean Paul Gautier and Vivienne Westwood. It’s kind of like the hybrid between these things.

Also, clothes I’ll be wearing on stage and I’ll make sure that they get seen more than one time.

I know that your new album comes out in October. Are there going to be any pieces of clothes that fans would be able to wear as well? Are they going to be merchandised?

Yeah, maybe. I hope so. My goal is always to be able to share the things that I create. So that’s always an intention, but like I said, it’s really about quality and partnerships, and all these other things. So I’m just more in the state of making things and putting them into the universe and seeing what the universe brings back to me. That’s where I’m at with self-releasing my album and not really asking for any help financially from any labels or anything like that. I’m really figuring out what it is I want and what my vision is based on what I’m willing to give and then I can go from there. I’m trying to practice that across the board. I would love for that to be a thing. Currently, it’s just really in the beginning stages. It’s like I’m in incubation and my album coming out is the start of me coming out of the incubation.

Do you have any advice or strategies for someone who’s looking to carve out their own style identity?

Oh, for sure. First, do whatever the fuck you want. All right?

Do whatever the fuck you want.

If you want to wear a blazer top with a plaid skirt with furry socks and grass slippers, tap in it. I feel like adventuring in a space where there are no consequences is where you take the most advantage of adventure. You’re trying on different outfits, it’s not like skydiving. If you put on an outfit and you don’t feel good in it after you try it on, you put on another one. Explore as much as you’d like.

I would also say do some research. If you like a designer, look up why you like that designer. Try to find out why you like them. Who’s their favorite designer? What was their claim of fame? How do they feel about where the state of style and fashion is and what’s their perspective? What was their childhood like? Do some research, do some digging, and you’ll find more connectivity to what it is you feel so drawn to subconsciously and you’ll embody it more.

You mentioned if somebody likes a designer reach into that. Lean into that. Who are some designers and brands that you think are taking chances right now that are impressing you personally?

I like Marni a lot, I like Bottega, I like Bode, I like Aime, Leon Dore, but then I like traditional. I like Guess originals a lot, what they’ve been doing lately, just practical things. As far as footwear, I really like Reese Cooper, I like this company in Italy called Cassia. I got a lot of friends who do streetwear stuff. I really like Daily Paper a lot. I’m a big fan. I got a couple of pieces from them that I wear a lot. Most of the stuff I get is one-on-ones where I go to these boutiques and there is only one shirt to be found from 1930. And I’m like, well, it’s mine now. I’m very much in a collection mode.

For example, I don’t wear dresses, but I have a lot. I collect them. I got all these different colors and textures just because I want to see why and how they’re made. I have all this interest in the history of things, so that’s what I’m drawn to more than, oh, this is hot and new and everybody’s wearing it so I should get it too. That’s not really my energy.

In your personal opinion, do you see that there’s a change in the way people dress and the fashion sense throughout the world? Do you think people are more aware of their style nowadays?

That’s a great question. I think the pandemic really affected how people look at clothing and I think it turned more into uniform-based things. That’s why Essentials is so successful. Jerry Lorenzo really has it figured out. Designers like him who make things uniform based. So it’s easier for people to pick what they’re going to wear every day. I think that’s a lot of what I see happening. People have designed their own lifestyle as far as what a uniform means to them. And with that, everything else is easier to make decisions, or it’s easier to find yourself in a ritualistic space, or having these things that you go to that you find comfort in or you feel safe in.

I think people’s style is becoming way more intentional than it was other than thinking they have to look “cool.” That’s a part of it, but it’s like I got to feel good in this and I got to feel like it’s speaking to me and I’m being genuinely how I feel right now and not trying to put on a show for people. The pandemic kind of shifted that when people were just home and they were in pajamas all day. They’re like, okay, now we get to go back outside. I would love to be in pajamas all day. I’d rather just be in clothes that feel like I’m at home. So I think there’s a bridge happening between the two worlds, which is the really high fashion couture stuff, and then the really practical essentials of the world. Companies like that who do really well at making clothing that is super well cut, produce really good products, and not have a logo all over the place.

Which artists over the decades have you personally thought had the best style?

Steve Lacy definitely understands what he wants to portray and what he wants to express in his style. He’s definitely in the explorative mode and he’s curated as far as the designs he likes and things like that. Channel Tres for sure. He got the crop top game on smash. And as far as in general, if I zoom out, I don’t know. I really love Prince. He’s one of my favorites. I mean, he’s at the top. I think about Kanye and the Yeezy, Dark Fantasy, and Saint Pablo eras. What Pharrell’s doing right now with Louis Vuitton and how he’s having the conversation in his music and in his visuals is great. Tyler, The Creator is another one that goes crazy. He’s highly stylish. He definitely understands what it is he’s trying to express in his style. I’m damn sure he doesn’t got no stylist.