How Boston hip-hop standout Cakeswagg turned a passion for performing into a badass athletic brand
Some people are just born with it.
They grow into their natural vibe with a cool nonchalance, never looking too far in the rearview.
For Boston hip-hop artist and outfitter-entrepreneur Cakeswagg, there’s not even a long list of scrapped rap names left behind in her journey to the point of working full time in music and fashion. Friends and followers have called her Cakeswagg since her days spent growing up in Roxbury and riding the METCO bus to Natick public schools, where early on her moniker morphed from Pancake to its current fully baked form.
“That’s when the word ‘swaggy’ was cool,” she laughs. “Honestly, I was originally Cakeswagg. At one point I was going to change my name to Cake Boss, because I really like the show, but when I came back into music like four or five years ago people would still see me and be like, ‘Hey, Cakebodybagswagg.’”
Long before she became known for trampling tracks with ambidextrous flows equipped to roll across all contours, she sharpened her performance knives in makeshift studios set up by friends in basements and in theater and ensembles, including the iconic chorus powering Boston’s annual retelling of Black Nativity by Langston Hughes.
And before she had actual fans who could purchase her signature gear, Cakeswagg was adept at setting trends for high school friends, though not always intentionally.
“In high school I was super retro with everything,” she says. “I was wearing V-necks and khakis from the ’80s. It was all my mom’s, it’s what we had, but that’s when all the girls were wearing oversized sweaters, in ’07-’08.”
As an artist, Cakeswagg learned from the jump that everything from work ethic to style was as important as the music itself. Leaning into her background as an influencer in real life, a few years ago she started streamlining her efforts.
“I’ve always liked the marketing aspect,” she says, “but it definitely took some refining, finding the balance where being me is still super-duper marketable. I can be me on social media all day, but it still has to be marketable. …
“I recently went back and rerecorded some of my freestyles that didn’t get a lot of views, but I changed them,” she adds. “I styled them differently, changed the video quality, and some of them skyrocketed. It was the same video, but those other aspects matter. People want to see your uniqueness—Do you have cool hair? Do you wear cool vintage T-shirts?”
As Cakeswagg sings on her Candy Cake Season EP, “No limits, no gimmicks / Take a minute, or you gon’ miss it.”
She says, “Whatever it is, you need that likeability, the parts of your life that don’t even have to do with music have to do with music when you are an artist. People don’t want to see the same thing every time they see you. You need a different unique factor each time. You need to dig into your creative bank. And as an artist it’s hard—you need to push yourself.”
That push and relentless drive is real for Cakeswagg. Prior to the pandemic, she was averaging more than one show a week. It was from that experience that her stint as an exercise personality and clothier was born.
“Strong Black Girl literally came from me doing music,” she says. “I used to bartend, and when I switched to being an artist full time, I was gaining weight. I had a show [in 2019], and after my set I was out of breath, and I was like, Something’s gotta give. So I started doing high-intensity workouts. I had to, I was doing like 60 shows a year. I was doing it to perfect my performance, but in doing that I toned up a lot and lost a bunch of weight.”
But the weight was just the surface part of it. In seeing fans and friends react to her slight transformation, her wheels started turning.
“When I was stronger in the physical sense, I was stronger in the mental and musical sense too,” Cakeswagg recalls. “People would ask me about losing weight, and one of the things I would advocate for is being strong. A lot of women assume that if we lift, we’re going to be bulky. But there’s a lot of beauty in being strong. I started debunking the myth, making the word ‘strong’ feminine.”
In chronicling her progress on the socials, she saw right away that fitness was a natural lane for her. Within months, an idea for a business blossomed, followed by a strategy to build up from the grassroots rep and contacts she had honed through hip-hop.
“People started asking, ‘Where’d you get this?’ And, ‘Where’d you get your shirt?’ And I was like, I’m making Nike and all these other brands a lot of money. I should be marketing for myself because there’s my own story in that. As a girl, we get a lot more criticism about the way we look. I was like, How do I turn this around to work for who I am? Then it was like, How do I make my brand different? And representative?”
There’s also the whole issue of not crossing streams. Though Cakeswagg sets up merch booths with SBG tops and stretch pants at every show—she says a solid sales outing can mean more than $500 on top of what she earns for her set—the brand can also stand on its own. Just think of Diddy’s link to the preferred vodka of countless celebrities: “You might like Ciroc,” she says, “but you’re not a Diddy fan. I wanted to find a way to make SBG a part of me, but also separate for those outside of my direct fan base. It’s representative of me, but it’s not Cakeswagg Apparel.”
It’s not just threads either. Over the past two years, Cakeswagg also earned her certification in personal training, and works with clients out of Crunch in Roslindale and in some private locations. That immersion has helped fuel sales, she says, especially through Instagram. Otherwise, SBG has been riding high on good old-fashioned word-of-mouth and customer appreciation.
“The most traffic has been sort of like the pop-up shops around the city,” Cakeswagg says. “People will buy something with shorts or leggings, they’ll like it, then they’ll come back and buy more. Most of my growth has been from performance. Women have tons of leggings, but then we have our favorite pair.”
According to her plan, this year she’ll also be making your next favorite track to match those bottoms.
“What I’m trying to do is to switch it up and do collections. Sort of like Ivy Park or Fenty,” she adds. “They’ll drop a collection, and if you get it you got it, if you miss it you miss it.
“I’m aiming to drop six collections that I have in the vault. I’m trying to figure out how I want to incorporate songs into them, if I can tie the collection into some of my bigger shows, but the direction I want to go in is exclusivity.”
A Queens, NY native who came to New England in 2004 to earn his MA in journalism at Boston University, Chris Faraone is the editor and co-publisher of DigBoston and a co-founder of the Boston Institute for Nonprofit Journalism. He has published several books including 99 Nights with the 99 Percent, and has written liner notes for hip-hop gods including Cypress Hill, Pete Rock, Nas, and various members of the Wu-Tang Clan.