Nan James built Madrugada out of a backyard shed in Roxbury, and now the neighborhood-born clothing brand is planning its next move: a permanent storefront on Columbus Avenue in Boston's South End, with a lease expected to be signed this fall. The brand has already drawn attention from NBA star Jaylen Brown and rappers YG and DJ Mustard, and its recent pop-up in Downtown Crossing pulled in shoppers from as far away as Spain and Japan.
James incorporated Madrugada in 2019, according to Axios, but her path into fashion started years earlier. She began selling embroidered caps in 2016 before expanding into full clothing lines that same year, per the outlet's reporting. Madrugada operates under the parent company Summer In Roxbury Inc., and the name itself means dawn in Spanish, a nod James has described in terms of her personal philosophy that out of darkness, a new light emerges, according to background from BostonMan Magazine.
James, a Roxbury native who now splits time bicoastally while working in the television industry, set up a shed in the backyard of her childhood home in Roxbury in 2021, and it became a destination for local shoppers. That shed came down in early 2025 after James' family sold the house, but the brand continued through pop-ups that year, Axios reports.
A Downtown Crossing Test Run
Madrugada's most recent pop-up landed in Downtown Crossing, occupying a vacant storefront at 39 Winter Street for nine days. The nine-day run happened through a partnership with real estate firm Gazit Horizons and the Downtown Boston Alliance, which helps connect local creators with vacant retail space downtown. It gave James a chance to test brick-and-mortar retail ahead of a permanent location, and the response reportedly reached well beyond Boston, with customers from Spain and Japan stopping by.
That pop-up appears to have reinforced James' instincts about the brand's trajectory. She told Axios she felt something positive was coming as she looks toward the South End expansion.
From Madison Park to the Runway
James credits her design foundation to Madison Park Technical Vocational High School, Boston's sole public vocational high school. She told Axios that Madison Park taught her how to design clothes, screen-print and shoot commercials, and said everything she learned came from the school. Madison Park hosts Massachusetts Chapter 74-approved programs in Design and Visual Communications, according to Boston Public Schools.
That technical training eventually connected Madrugada with Fall River-based Vanson Leathers, a motorcycle apparel brand known for handcrafted garments, as detailed by BostonMan Magazine. The collaboration produced the Vanson x Madrugada Star Jacket, which reimagines Vanson's classic 1975 star design with James' childhood home logo worked into it, and retails for $1,499. Another collaboration between the two brands is reportedly in the works, per Axios.
Celebrity Reach Beyond Massachusetts
The Vanson x Madrugada partnership has helped push the Roxbury label onto a national stage. DJ Mustard, who has toured with Kendrick Lamar, wore a Vanson x Madrugada motorcycle jacket, and rapper YG was photographed in the Strawberry reimagined 1975 Vanson x Madrugada Star jacket in May 2024, according to a Madrugada Clothing Facebook post. Jaylen Brown has also given the brand attention, per Axios.
Alongside the leather collaborations, Madrugada's core lineup leans into neighborhood pride, offering items like Roxbury University hoodies and localized Boston collegiate graphic t-shirts, according to the brand's own product listings. That blend of hyper-local identity and celebrity-driven visibility is what James appears to be betting will carry over into a permanent South End address. Whether the Columbus Avenue lease can preserve that Roxbury connection as the brand scales beyond pop-ups remains to be seen.
