From Santo Domingo to Brooklyn: The Launching of a Caribbean-Inspired Leisurewear Line

How UVA Alumnus, Rey Massey, is re-imagining the leisurewear 
scene all while paying homage to his Caribbean heritage.
Modeled by Lauren Lord, a UVA Alum (Class of 2019) of Jamaican heritage, who lives in Brooklyn, New York.
Modeled by founder, Rey Massey (left), and Gabe Bracy (right), a fellow UVA Alum (Class of 2018) who lives in Brooklyn, New York.

December 17th, 2020 -— We caught up with Rey Massey (COMM ’19) to learn about the launch of his new brand, D’JAIN. A luxury Caribbean-inspired leisurewear line, their debut collection, D’JAIN WINTER20, dropped December 5th and is available for purchase until December 19th. Read our interview below and learn more about the project:

What inspired you to start D’JAIN?

The initial inspiration to start D’JAIN was drawn from my summers spent living with my family in Santo Domingo.

My mom spent the first quarter of her life growing up in the Dominican Republic, but decided shortly into her twenties that she wanted more opportunities for herself and her eventual family.  She immigrated to the United States in her mid-20s, learned the language, and started a family here, however her heart never really left the Dominican.  Since leaving, she became hyper cognizant of how important cultural immersion is to preserve heritage across generations, specifically for my sister and me. Every summer we would make the trip to the Dominican to stay with my Tío Manolo and my cousins, to ensure we wouldn’t forget our roots.

As a child in the Dominican Republic, our summer days consisted of a few staples: my cousins and I playing baseball in the street with a broom handle and tennis ball (really whatever we could get our hands on), constantly bothering my mother for spare pesos to buy empanadas and walking up to our local street vendor billowing “AGUUUAAAACATTEE!!” down our block. Life then was simple, but beautiful.

Following each summer, I’d reluctantly fly back with my family to the states, start a new year at public school, and begin my re-adjustment back into American culture. As years passed, I realized that as soon as I’d return, my memories spent in the Dominican Republic would fade as I would become re-immersed into our American way of life. Homework, sleepovers, and soccer practice quickly consumed my priorities.

This cycle of being immersed in my heritage then dropped back into American culture continued until I graduated from the University of Virginia in 2019.  Following graduation, I promptly moved to New York City to chase my dreams.  Upon arrival, I immediately began receiving flashbacks to my trips back to the Dominican Republic: overhearing Spanish on the subway, grabbing food with spare cash from street vendors, and even seeing kids play ball in the street, just like I did so long ago.

Reaffirmed by the cultural melting pot that is New York City, I began D’JAIN with the goal to merge my Caribbean heritage with my passion for business to build something bigger than myself.

Can you tell us a little bit about the collection? Such as the motivation behind the designs and the process of building it? 

Our debut collection, D’JAIN WINTER20, is comprised of 12 pieces, each inspired by the warmth of the Caribbean. Our design framework could be summarized as a light touch, with intentional execution.

Building D’JAIN into a brand has been underpinned by a process of constant ideation, revision, and diligent execution. Above all, we’ve found success in taking time to reflect on roadblocks we’ve come across along the way. Through this thoughtful reflection process, we’ve found it to be instrumental in turning what some would call “mistakes” into opportunities to learn. Each setback we overcome prepares us to be a better brand in the future.  

What’s your vision for D’JAIN and goals for it moving forward?

Our overarching vision with D’JAIN is to build community through delivering high quality, luxury apparel that pays homage to Caribbean and Latin American Culture. We strive to provide opportunities to underrepresented individuals within fashion, and as we grow, we will continue to do so at a greater scale.

In 2021, we plan to take our goals to the next level: we will begin manufacturing our garments in Santo Domingo, in an effort to create jobs, bolster the local economy, and fight income inequality.

Where can we find D’JAIN?