Talk Shop: "High-End Thrifting" with Bay Area Rapper Caleborate

A conversation about fashion, #freetheankle, and GOATs ensued.

By Mustafa Shaikh Apr 12, 2017

In late 2015, Atlanta-based producer Sonny Digital was over at my apartment in the Hayes Valley neighborhood of San Francisco. I wanted to turn him onto some under-the-radar Bay Area rap, so I threw on a track from a guy named Caleb I’d heard a few days earlier.

Sonny was feeling the song, and we carried on as Caleb's EP continued to play. A couple joints later, Sonny piped up: “Man, who is this? Logic?”

“Nah, it’s still that dude Caleborate I was telling you about earlier,” I replied.

Today Caleborate—born Caleb Parker—is trying to flip his Bay Area following into a national presence. Last year he dropped his album 1993 to critical acclaim, and is now working on his next offering.

I caught up with Caleb last week in San Francisco to have a conversation about style. I gave him $40 to spend during our outing—anything he didn't spend would be returned to the TrackRecord accounting department.

—Polaroids by Mustafa Shaikh. Artwork by Fer Gonzalez.


“Corporate shit”


Our first stop was the Levi’s flagship store on Market Street, in the heart of San Francisco’s downtown. Caleb actually used to work there a few years ago.

“I’m so glad I don’t work here anymore,” he tells me as we browse the denim store. “Just corporate shit working for someone else. When you work a job like this, it changes you.”


The $158 Hawaiian Shirt


Caleborate and I stumble across a floral printed shirt. “It’s crazy how much this shirt costs,” he says. “It’s not even a nice shirt. You could find this at Ross.”

I look at the price tag. Me: “Damn, this is $158?”


Beanie Game = Strong


Caleborate tells me he prefers his headwear to look brand-new. “I actually threw away five beanies last night,” he says. “Some stuff looks less cool when it’s worn in. Beanies are one of those things so I try to keep them fresh.”


“High-end thrifting”


We eventually decided to head to Forever 21. Caleb was confident that he could put his $40 to good use there.

“Forever 21 or H&M is where to shop to be broke, and not look broke,” he says. “This and thrifting. [Shopping at Forever 21] is high-end thrifting.”


“Bruh, Wayne is culture.”


If there’s one fashion trend that 2016 will be remembered for, it was the acceptance of band merch as everyday wear. At Forever 21, we stumble on a shirt featuring the artwork from Lil Wayne’s first album, Tha Block is Hot.

“I remember Wayne on 106 and Park. I remember when I saw the "Mrs. Officer" video. Bruh, Wayne is culture. Wayne is a big deal to me. He is really one of the GOATs.”


“It’s an experience.”


While the Lil Wayne shirt catches his eye, Caleb ends up gravitating towards Forever 21’s basics. Basics are, by their very nature, less identifiable as belonging to a specific brand.

“I don’t want some nigga to be like, ‘Oh, I got that same hoodie as Caleborate.’ When people meet me, I want them to think my fashion is dope. Like when you meet your favorite rapper, and it’s an experience.”


Breaking the Bank


A Forever 21 cashier asks Caleborate how he found everything today. Without skipping a beat he replied, “I went in.”

In the end, Caleb dipped into his personal funds in order to pick up a pair of overalls, a shirt, and a windbreaker from Forever 21.


“Overalls are lit.”


“Since I jump up and down a lot [when I perform], it’s real nice to not have to worry about some of those concerns. When you wear shorts, what if my shorts come down?” Caleborate offers. “Or if you have a chub, and you don’t want people taking pictures and saying that your chub looks weird. Overalls are lit cause they’re meant to be loose. You have so much room and space. I’ve been trying to find the perfect performance wear. Is it shorts? Is it baggy jeans? Maybe it’s overalls.”




After 1993 dropped, Caleb started his #freetheankle campaign: shoes, no socks, and the jeans rolled up just enough to show your ankles. He recently dropped the tag to avoid it becoming a gimmick that his career was attached to.

“Honestly, I never really explained #freetheankle,” he tells me “I started cuffing my pants and flooding them because I saw women wearing capri pants and it looked dope. It just made the shoes look so clean, but then niggas would clown me. I turned it into a thing and it caught on. I just thought it was dope fashion, and I was saying as a man it was fine to do it.”


Give Me Two Pairs


I thought it might be a fun to end the trip at Ross. You never know what you might come across there. To my amusement, Caleborate gravitated towards a pair of water shoes.

“I have never had money to buy nice shoes,” he says. “[If I had the money] I’d go somewhere where they have the Nikes, Adidas, Stan Smiths and buy a lot of shoes.”


Mustafa Shaikh is the founder of contemporary menswear brand, 36 Chambers and is based in San Francisco, CA.