The Magic of Vintage Lives at Lucky Fool with Kay McMillen

By Natalie McCarty

In a city like New York City, clothing is rarely just clothing. It becomes armor, costume, memory, or rebellion depending on who’s wearing it and where they’re headed that night. Vintage carries that feeling especially well. Each garment arrives with its own history: dresses that may have spun beneath disco balls decades ago, jackets that have ridden the subway through eras of change, pieces that have waited patiently for someone new to claim them.

For Kay McMillen, the Brooklyn-based founder of Lucky Fool Vintage, those garments are stories waiting to be lived again.

Provided by Kay McMillen

McMillen has spent the last five years building Lucky Fool Vintage into something that feels less like a living creative space. Operating from a Bushwick showroom, the lesbian-owned brand has become a destination for musicians, artists, and style experimenters across the city. Racks of expressive, high-femme vintage line the space, shifting easily between decades: glittering party dresses, dramatic silhouettes, delicate slips that feel as though they belong on stage as much as on the street.

Styling people in those pieces has become one of the most fulfilling parts of McMillen’s work. Watching someone slip into a garment from another decade and suddenly recognize a new version of themselves is, for her, the entire point.

Lucky Fool did not begin with a grand business plan or even a storefront. It began with a closet that had grown wildly out of control.

“My vintage collection was completely overrunning my life,” McMillen says.

For years she had been collecting pieces simply because she loved them. Eventually the collection spilled into every available corner of her apartment. The solution, at first, was simple. She began lending garments to friends, pulling pieces for nights out, performances, or photoshoots.

In doing so, she discovered that the real joy wasn’t only in finding vintage, but in watching the clothes continue their journey.

“I realized how much fun I had stewarding vintage pieces to go off into the world and live a life.”

The project grew organically from there. McMillen started selling at small markets scattered throughout New York City, gradually building a community drawn to her eye for playful, expressive pieces. Over time that momentum evolved into the Lucky Fool showroom now tucked into Brooklyn’s Bushwick neighborhood.

After living in New York for nearly a decade, the city’s sensibility has naturally filtered into her curation. New York has always rewarded individuality, especially the kind that borders on the theatrical.

“Living here has taught me to love the fun, the freaky, and the weird,” McMillen says. “That translates directly into the types of vintage I curate.”

Provided by Kay McMillen

The personality of Lucky Fool follows that same instinct. McMillen describes the brand as whimsical, high-femme, and a little bit freaky. At its core, it is about curiosity and exploration rather than perfection.

In McMillen’s view, personal style doesn’t arrive fully formed. It develops through experimentation, sometimes awkwardly.

“I genuinely believe you need to wear a hundred bad outfits to get to the good one,” she says. “You have to be willing to dress badly sometimes.”

The willingness to experiment, she explains, sharpens personal taste. Every strange combination and every outfit that doesn’t quite work teaches you something about what does.

“Being explorative with your style trains your brain to figure out what you actually like to wear,” she says. “It helps that little personal-style worm in your head become more selective.”

Despite being surrounded by extraordinary garments every day, McMillen is careful about what she keeps for herself. The bar for entering her personal wardrobe is extremely high.

“I have to be gobsmacked,” she says. Occasionally she finds a piece so good she’s grateful it doesn’t fit her, simply so it can make its way onto the showroom floor. But if something truly moves her, or if she knows she will wear it endlessly, it earns a permanent place in her own collection.

While vintage always carries a sense of history, the community forming around Lucky Fool is firmly rooted in the present. McMillen is outspoken about the fact that the brand is lesbian-owned, a detail she intentionally foregrounds.

“I’m insistent on announcing that Lucky Fool Vintage is a lesbian-owned business,” she says. “I want queer and trans people to know they’re welcome in our showroom.”

Her identity shapes the environment she has built there. McMillen often finds herself thinking about the generations of queer people who came before her, many of whom never had the freedom or safety to dress the way they wanted.

“I’m constantly thinking about queer ancestors who weren’t granted the opportunity to wear the clothes they loved,” she explains.

Inside the showroom, that history quietly transforms into something joyful. Customers try on glittering dresses, bold silhouettes, and hyper-feminine pieces that might once have felt out of reach. Sometimes people are simply excited to find size-inclusive vintage, which can be difficult to track down. Other times, the experience becomes more emotional.

“I’ve had customers tell me they’ve had really meaningful experiences in our space,” McMillen says. “Sometimes they’re just happy to find the clothes. Other times they’re excited to be queer and frolic around in femme outfits while we hype them up.”

Those moments, the laughter in dressing rooms, strangers cheering each other on, someone seeing themselves differently in the mirror, have shaped the way McMillen approaches her curation.

“They’re the moments that make me excited to keep bringing in really fun, really femme vintage.”

Although running a small business requires independence, Lucky Fool has also grown within a tight-knit network of fellow vintage creatives. McMillen frequently collaborates with shops such as Messy Jessy Vintage and Armoury Shop, relationships that reflect her belief in collaboration rather than competition.

“There’s a lot I can accomplish on my own,” she says. “But I truly believe there’s no ceiling when I’m working with my studio mates.”

The vintage industry, she notes, sometimes carries quiet pockets of rivalry. But the community she works alongside has chosen something different: shared momentum.

“Vintage is a field dominated by women, and I think it’s a real act of love when we show up for each other the way we do,” she says. “Every win they get feels like a win for me too.”

In McMillen’s case, that support is deeply personal.

“It’s just a bonus that two of the women I collaborate with happen to be my best friends.”

Provided by Kay McMillen

Looking ahead, she imagines Lucky Fool continuing to expand its reach, particularly through styling work. Creating a full vintage look, seeing pieces from different decades come together into something entirely new, remains one of the most exciting parts of her work. A storefront may eventually follow as well.

What won’t change is the spirit behind the brand.

“Lucky Fool will always be curated for the women, freaks, and queers who want to have fun with their clothes,” she says.

If the perfect New York moment were to arrive tomorrow, McMillen already knows what it might look like. Perhaps one of her dresses appearing on stage, worn by a pop star whose energy matches the theatrical spirit of the racks in Bushwick—someone like Zara Larsson or Chappell Roan.

But even without that spotlight, Lucky Fool has already carved out something meaningful. Inside the showroom, vintage garments continue their strange and beautiful cycle, moving from past to present and back into the world again.

And in a city that thrives on reinvention, that may be the real magic of vintage. It doesn’t preserve the past so much as release it, waiting for someone new to step into the story.