Seniors Redefining Cool in New York City

Every morning, Debra Rapaport, a style expert, wakes up in her Manhattan home and prepares for the day. Her vivid, maximalist fashion perfectly suits her Instagram presence, where she has garnered a following of 109,000 enthusiasts.

On Thursday nights, the duo of Gerard Delito and James Valentino are a sight to see at a trendy local bar. Meanwhile, Lisa Carroll, an entrepreneur and multi-talented performer, is busy celebrating her new book while brainstorming her next big idea.

Surprisingly, these trendsetters of New York City aren’t part of the Gen Z crowd. In fact, they’re quite a bit older—old enough to be the great-grandparents of today’s youngest influencers. Rapaport is 80 years old, while Valentino and Delito are 82 and 89, respectively. Carroll, a vibrant former performer and toy creator, recently turned 96.

Welcome to the era of senior hipsters, where aging gracefully is out, and collective aging is in. This group of active New Yorkers over 70 is taking over bars, social media, and the fashion scene by storm.

While actor Tony Danza, 74, captivates audiences at Café Carlyle, iconic fashion figure Norma Kamali, 80, is shattering the stereotype that older generations are out of touch with technology. She’s embracing AI, sharing tips on longevity, and inspiring others. Meanwhile, Laurie “Hey Girls” Cooper, reportedly 86, is giving surprise dating advices in bars across the city.

“Hipster? To me, it means being cool and aware of the world around you,” Carroll shared when asked if she identifies with the term, then quickly launched into a festive rap wishing readers a “cool yule.”

“Absolutely, I see myself as a hipster,” she affirmed.

These individuals aren’t searching for eternal youth; what they seek is to truly live in the moment, regardless of how many moments they have left.

Lisa Carroll, 96: Rapper, Singer, Author, Toy Entrepreneur

Lisa Carroll’s story, originally Faye Blossom Mogul, is like a classic Hollywood tale filled with fortune and misfortune. It includes narrowly escaping a tragic car accident that claimed four lives before she launched her career.

Defying doctors’ predictions, Carroll regained her health and became known for her cabaret performances throughout New York, Los Angeles, and beyond. She even starred as a stand-in for the legendary Carol Channing in the touring production of “Hello Dolly” back in 1965-66.

Fast forward over 60 years, and she’s still going strong. Recently, she released a new children’s book titled “Lights, Camera, Lisa!” co-authored with Joseph P. Camel. The story revolves around a young woman aspiring to be in the limelight.

“She’s incredible and an inspiration to so many,” Camel, 38, remarked about Carroll. “Once she dreams something, she makes it happen.”

Carroll has also created educational toys, including a character named “Hip Hop Hamilton,” inspired by a Broadway hit. This unique teddy bear dances and raps to an uplifting song she wrote called “Dream Big.”

In addition, she produced a hip-hop holiday album, “Wrapping Up Christmas: Lisa’s Hip Hip Homies,” and authored a children’s book about overcoming pandemic fears titled “The Big Bad Coronavirus: And How We Can Beat It!”

“What keeps me going is helping young people believe they can achieve their dreams,” Carroll expressed.

James Valentino, 82: Singer | Gerard Delito, 89: Pianist

When James Valentino first visited Mimi’s Restaurant and Piano Bar in Midtown East back in 1962, he had different intentions than just making music.

At age 19, he was there to meet women—he had heard airlines stationed stewardesses in the area. But now, he returns each Thursday night to sing with pianist Gerard Delito.

This duo, aptly named Forever Young, entertains audiences of all ages with timeless classics like “My Way” and “What I Did for Love,” with patrons often joining in.

Valentino played clarinet in his high school band and even worked with a doo-wop group before pivoting to a corporate job as a programmer. Eventually, he returned to music, joining the New Horizons Band at Third Street Music School, where he met Delito, who began taking piano lessons at 60.

“It’s all about what’s in your soul,” Delito shared, hinting at his passion for music. They perform at Mimi’s regularly, sometimes joined by Carroll, who adds her own flair with a rap version of “Hello, Dolly!”

Debra Rapoport, 80: Artist, Designer, Fashionista

Debra Rapoport has always stood out. From the age of three, she adored dressing up. While other children played with dolls, she and her sister donned their mother’s old clothes and took center stage at home.

“My mom always supported that creativity,” Rapoport recalled, embracing the peculiar yet expressive style that defines her today. Layered outfits, vintage scarves, bold jewelry, and even accessories crafted from recyclable materials are staples of her wardrobe.

The hat is her signature piece. “It frames the face,” she said, referring to how important it is to her overall look.

Throughout her career, Rapoport has taught and exhibited her art, which is now showcased in prominent museums worldwide. Yet, the act of dressing up remains her form of meditation.

“It’s a healing process,” she noted. “It helps me connect with myself and ground my thoughts.” And, of course, it keeps her undeniably cool.