Tessa Thompson Turns Fashion Into Connection on The Good Buy
tessa thompson used Harper’s Bazaar’s podcast The Good Buy to spell out a style rule she applies on the red carpet: clothes should invite connection, not create distance. She spoke with editors Leah Chernikoff and Lynette Nylander about vintage, identity, and why a 1988 Vivienne Westwood suit still fits her thinking.
Vivienne Westwood, 1988
“I am wearing this little skirt suit from Vivienne Westwood Spring/Summer 1988 collection,” Thompson said, adding that the piece was apparently owned by photographer Henny Garfunkel. The look is doing more than filling a red-carpet slot; it turns the appearance into an object lesson in how archive pieces travel through fashion, ownership, and memory.
“I love vintage and I really love imagining the stories of the clothes that you buy,” she said. Thompson’s interest in old pieces does not read as costume nostalgia. It is a working method, and she tied it to a broader view of dress that starts with interpretation, not trend-chasing.
Thrift Stores and 2014
“I grew up going to thrift stores with my parents out of necessity,” Thompson said, before noting that she later started to uncover incredible things there. That background gives her style choices a practical edge: the instinct for finding value in secondhand clothes comes from family routine, not industry affectation.
2014 marked one of the clearest early reference points in that public arc, when Thompson appeared in Dear White People. By then, she was already building a profile around complex characters and innovative storytelling, and she later extended that instinct off-screen by founding Viva Maude in 2021 to champion underrepresented voices and stories in entertainment.
Prince, 1985, and Red
“For me, fashion had so much to do with identity,” Thompson said, and she stacked that idea with a family image from 1985: a photograph of her mom in an oversize men’s blazer and a button-up. She also pointed to Prince as one of her biggest inspirations, saying, “One of my biggest inspirations, both for fashion and life in general, is Prince.”
“I was a massive Pee-wee Herman fan as a kid,” she said, and the mix of references helps explain why her wardrobe resists one-note branding. Even her red-carpet color choice came with limits: “In my personal wardrobe, I don’t own a lot of red,” she said, while adding that she knew she needed to wear red. The result is a fashion vocabulary built around intention, not spectacle for its own sake.
For anyone watching how Thompson uses clothes in public, the takeaway is straightforward: she treats fashion as a narrative tool, and she is selective about the stories she wants the wardrobe to tell. That makes the next appearance less about a single look than about whether the clothes still carry the same balance of openness, history, and self-definition.
The Good Buy
Thompson’s podcast appearance gives her public style a sharper frame, especially because she was speaking on The Good Buy rather than in a promotional photo caption. With Leah Chernikoff and Lynette Nylander pressing the conversation toward vintage and meaning, she made the case for dressing in a way that brings people in — a cleaner read than any runway mood board could offer.
