Adelina Winfield is an artist, author, former fashion designer, mother and grandmother. She’s also the creator of Fly Granny BK, a highly active platform dedicated to highlighting the perks of aging and encouraging women over 50 to embrace and find positivity in their life changes.

In this episode, Adelina shares her remarkable story, including growing up in Brooklyn, raising her two sons, jumping back into the world of dating after her divorce, and dealing with ageism within the fashion industry. She emphasizes the importance of being confident and proud of aging and discusses the joy that comes with discovering a sense of individuality in your later years. Throughout this conversation, Adelina’s warmth and authenticity really shine, and we’re excited to share her insights with you!

The Journey from Fashion Maven to Influencer

Adelina Winfield, an influencer over 50, defies age stereotypes and embraces life’s transitions. Her journey into the world of influencers didn’t happen overnight.Adelina’s story is one of perseverance and passion, which is particularly evident in her rich background in the fashion industry.

Hailing originally from Brooklyn, Adelina’s roots are deeply embedded in the vibrant culture of the city. With a career spanning over 30 years in fashion, she reminisces about her days as a designer, crafting both children’s and women’s clothing for iconic brands like Guess Kids and Jay-Z’s Rock-A-Wear. Her expertise wasn’t limited to just mainstream labels; Adelina’s creative touch extended to vintage clothing and T-shirts, demonstrating her versatility and flair for style.

Throughout her tenure in the fashion world, Adelina jet-setted across the globe, drawing inspiration from European travels and immersing herself in the latest trends. Her passion for fashion ran deep, shaping her identity and fueling her professional success.

However, as Adelina entered her 50s, she found herself confronting the harsh realities of ageism in the industry. Despite her wealth of experience and talent, she faced challenges as younger talent began to dominate the scene. The landscape shifted, and Adelina found herself at a crossroads, navigating layoffs and the daunting task of starting over.

But Adelina’s resilience shines through as she shares her journey of rediscovery. Despite the setbacks, she refused to be defined by age or circumstances. Her transition from the fashion world to becoming an influencer was fueled by her adaptability and determination to carve out a new path.

Reinvention and New Beginnings

In a bold decision, Adelina embarked on a new chapter in her life. Feeling the need for change after a divorce and her kids leaving home, Adelina took a leap of faith and relocated from her lifelong home in New York City to Austin, Texas. It was a move driven by a desire for something different and the allure of a city that resonated with her.

With her son in his final semester at university, Adelina bravely packed up her belongings, shed unnecessary baggage, and hit the road, leaving behind familiarity and embracing the unknown. Looking back, she reflects on the sheer audacity of her decision, but also acknowledges it as a pivotal moment that kick-started a journey of self-reinvention.

Moving to a new city meant starting from scratch—new friends, new surroundings, and a fresh perspective. It was a chance for Adelina to carve out a new identity and embrace the opportunities that lay ahead. The transition wasn’t without its challenges, and Adelina’s resilience shone through as she welcomed the adventure and made the most of her new surroundings.

Thankfully, Adelina’s move to Austin occurred before the onset of the COVID-19 pandemic, sparing her from the added complexities of settling into a new city during such uncertain times. Reflecting on her time in Austin, Adelina cherishes the experience—it was truly a transformative period in her life.

Yet, despite the excitement of her new beginning, Adelina shares that it didn’t completely erase the struggles she faced—particularly with issues like menopause-induced depression, which left her feeling disconnected from herself. Eventually, she returned to New York to seek the comfort of family while continuing her journey of self-discovery.

The Truest Beauty Comes from Self-Acceptance

On her journey of self-discovery, Adelina felt empowered to embrace her natural gray hair—a decision that was initially met with resistance. With encouragement from her son, Adelina claimed her inner “storm” (a term coined by her son in reference to the iconic X-Men character). She eventually took the plunge and stopped dyeing her hair. It wasn’t an easy decision, but with the support of her boyfriend, Dave (now her husband), she learned the importance of self-acceptance.

Adelina’s decision to document her transition on Instagram led her to connect with the vibrant “silver sister” community, where she found support and inspiration from others on a similar journey. Through patience and self-acceptance, Adelina found that embracing her natural gray hair was not just a physical transformation but a profound shift in mindset—an affirmation of her beauty and worth at any age.

Christina and Adelina’s conversation is peppered with humor and empathy as they discuss the complexities of aging and self-image. While Adelina’s journey may not resonate with everyone, her story serves as a reminder that true beauty comes from embracing who you are, inside and out, regardless of society’s expectations or norms.

Navigating the Dating World After 50

Another challenge from women as they age comes with dating. Adelina has experienced the complexities of dating as mature women, and she offers insights and encouragement based on her own experiences. Adelina shares candidly about the challenges of navigating the online dating scene after being out of the game for a while, especially for those who’ve recently gone through major life changes like divorce or widowhood.

Christina relates stories from friends who’ve ventured into online dating, highlighting the pitfalls and surprises that come with it. Adelina emphasizes the importance of being discerning and knowing what you want, drawing on the wisdom that comes with age to spot red flags and avoid disappointment.

Despite the initial apprehension, Adelina shares her own story of meeting her husband online, even though they lived thousands of miles apart. She challenges the notion of limiting oneself to a small radius for potential matches, advocating for openness to long-distance relationships and the possibilities they bring.

Navigating the dating world can be complex, and Adelina shares advice for women who are navigating the dating world after being married for a long time. She advocates for taking the leap and trying online dating, even if it feels intimidating at first. Curious? Many platforms offer free memberships so users can explore their options.

Before seeking a partner, though, Adelina stresses the significance of finding happiness within oneself. Being whole individually can allow two people to come together and complement each other rather than relying on each other to fill a void.

Adelina also suggests putting oneself out there by attending events where potential partners might be found, such as political gatherings or business meetings. She reminds women that love won’t find them if they stay home on the couch.

Staying Positive When Faced With Negativity

As an influencer, Adelina faces the challenge of dealing with negativity on social media, particularly regarding Adelina’s biracial marriage. Despite the overwhelmingly positive feedback, Adelina has encountered hurtful comments from a small minority of individuals.

However, rather than letting these comments bring her down, Adelina chooses to turn them into content, demonstrating resilience and positivity in the face of adversity. Christina chimes in, suggesting that jealousy might be at the root of these negative comments, sharing a personal anecdote about her uncle’s long-lasting gay marriage and how jealousy can breed negativity.

Christina and Adelina emphasize the importance of not taking hurtful comments personally—negative comments are more a reflection of the commenter’s issues than anything else. Christina shares a heartwarming anecdote about a friend teaching her son to respond to bullies with empathy rather than anger, echoing the sentiment that hurtful words are often a manifestation of the commenter’s own insecurities or unhappiness.

Adelina likes to focus on the positive and not let the negativity overshadow the joy she finds in sharing her life with her husband. She even created a humorous video in response to one particularly negative comment, showing that she’s able to brush off the negativity with grace and humor.

Dress for Yourself, Not For Society

Strict fashion rules based on age are a thing of the past. In discussing fashion for women over 50 and 60, Adelina and Christina agree that what’s most important is feeling confident in what you wear. There has been a marked shift away from traditional styles of previous generations, when women often dressed more conservatively as they aged. Instead, Adelina encourages embracing bold colors and experimenting with new styles that complement individual body types.

When Adelina took this advice for herself, she found that transitioning from a wardrobe dominated by black to incorporating brighter colors was quite uplifting. She also tries bolder prints and funky eyeglasses, enjoying the freedom of expressing herself through fashion at any age.

Age should not limit a person’s fashion choices. Wear the skirts and the shorts if it feels good regardless of societal expectations. 


In wrapping up the podcast, Christina asks Adelina two final questions: the greatest accomplishment since turning 50 and where she sees herself in 10 years.

Adelina proudly shares that her greatest achievement is her two sons, aged 40 and 31, who now acknowledge her wisdom and guidance. She finds immense joy in their growth and maturity, considering it more valuable than anything money can buy.

Looking ahead, Adelina envisions herself enjoying the warmth, possibly in Capri, Italy, savoring life’s moments and continuing to inspire women to live fully at any age. She emphasizes the importance of self-care after years of caring for others, encapsulating her philosophy with the mantra, “Every day is a gift. Open it and be present.”

For more fashion and inspiration, follow Adelina on Instagram at @FlyGrannyBK.

See her full interview here:

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