Ep. 16: Jennine and Kristen on reinventing yourself: fashion, work, and meaning in midlife
Release Date: 07/28/2025
Closet Philosophy
In this episode of Closet Philosophy, hosts Jennine and Kristen sit down with career consultant Dilara Casey to explore what it takes to reinvent your career and style in midlife. Even if you've taken a decade out from your career, Dilara has tops for everything from making confident pivots to navigating ageism. She shares practical strategies for reframing your story, updating your resume, and embracing change with authenticity. She also opens up about reclaiming personal style during challenging times and why staying true to your look can be a source of power. The conversation touches on...
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In this episode of Closet Philosophy, hosts Jennine and Kristen sit down with Denise Pines, an influential filmmaker and leader in the effort to normalize conversations about perimenopause and menopause. She’s a Peabody-winning filmmaker, health advocate, founder of Tea Botanics and WisePause Wellness, and president of the Osteopathic Medical Board of California. Together, they unravel the cultural silence around menopause and perimenopause, discuss Denise’s influential documentaries (The M Factor and upcoming Before the Pause, and explore how personal style, society, and women's...
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Jennine and Kristen dive deep into the complex experience of visibility for women as they age, sharing candid stories and discussing cultural, psychological, and societal shifts that impact self-expression and confidence beyond 40. This episode explores the challenges women face in retaining visibility, feeling confident, and expressing authentic style, offering hope and actionable insights for listeners. Key Topics: The first personal experiences of feeling invisible: Jennine and Kristen recount moments in retail and influencer settings where age influenced how they were treated. The myth...
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In this episode of the Closet Philosophy podcast, hosts Jennine and Kristen sit down with Cat Pierce—writer, artist, entrepreneur, and musician, best known as half of the band . Cat shares her inspiring journey of continual reinvention, highlighting how creativity flourishes at every stage of life, especially beyond the age of 40. The conversation delves into themes of overcoming societal expectations, building inner and outer confidence, and finding empowerment through personal style, beauty rituals, and creative experimentation. Cat discusses launching her beauty and lifestyle brand, Omen,...
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This week on Closet Philosophy, Jennine and Kristen sit down with fashion creator Angel Edme. Her bold style and fearless approach to self-expression embody what it means to use style as self-expression. Angel Edme is a fashion, beauty, and lifestyle creator based in New York—known for her razor-sharp style, unfiltered honesty, and a deep passion for helping people show up as their boldest, truest selves. She started behind the camera as a storyteller, and now she’s in front of it—empowering real people to reclaim their confidence through fashion, skincare, and creative self-expression....
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in this inspiring conversation, we talk with Alicia Johnson—global marketing strategist, Ford model, and author of . Alicia shares how she re-entered the modeling world in her 60s through a twist of serendipity, the challenges and biases that still exist for older plus-size women in fashion, and how personal style can be a radical act of self-acceptance. We explore the deeper meaning of authenticity, why self-trust is the foundation of showing up fully, and how movement—not dieting—can be a key to reclaiming joy. Alicia also offers practical tools for reconnecting with your body,...
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In this episode we are very thrilled to talk with Leah Elson—scientist, author, and viral science communicator—about the power of showing up fully as yourself, whether in a lab coat or a leather jackets. Leah has degrees from Harvard, Johns Hopkins, and USC, and has published more than 87 scientific manuscripts. But she’s just as known for her incredible eyeliner, tattoos, and bold, unapologetic personal style. We talk with her about how embracing her full self—pink hair and all—actually enhanced her work as a neuroscientist. We cover: Why personal style isn’t...
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Welcome to a special episode of Closet Philosophy where Jennine and Kristen open up about the challenges and rewards of reinventing yourself—especially after taking a work break to care for family or shifting gears in midlife. They share their personal journeys of returning to the workforce, navigating ageism, career gaps, and finding new purpose. In this episode, we discuss: Personal experiences of leaving and re-entering the workforce after motherhood or caretaking The surprising roadblocks and opportunities that come with a career gap Ageism and the difficulties faced by midlife...
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In this honest and often funny conversation, Jennine and Kristen talk with Isobel Schofield, founder of the iconic clog brand Bryr Studio, about style, aging, menopause, and power. The episode opens with Kristen’s reflections on how her personal style has evolved post-menopause — from abandoning painful heels to embracing the liberating truth of wearing clothes that actually fit. Then Isobel joins the conversation, and the three dive into how personal style is shaped not just by bodies, but by generational values, cultural shifts, and an ever-present questioning of the patriarchy. From her...
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What if your fitness journey wasn’t about chasing a smaller body—but about feeling strong, energized, and alive? In this empowering episode, we talk to Oonagh Duncan, multi-award-winning fitness expert, bestselling author of Healthy As Fck* (aka Ditch the Diet), and founder of the Feel Good Movement. We dive deep into what it really means to feel good in your body—at any size, at any age—and how fitness can help us reconnect with our power. Oonagh shares her journey from fat activist and actor to fitness leader, and how she’s redefining health for Gen X women and beyond. She breaks...
info_outlineWelcome to a special episode of Closet Philosophy where Jennine and Kristen open up about the challenges and rewards of reinventing yourself—especially after taking a work break to care for family or shifting gears in midlife. They share their personal journeys of returning to the workforce, navigating ageism, career gaps, and finding new purpose.
In this episode, we discuss:
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Personal experiences of leaving and re-entering the workforce after motherhood or caretaking
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The surprising roadblocks and opportunities that come with a career gap
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Ageism and the difficulties faced by midlife women in today’s job market
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The importance of meaningful work, creativity, and autonomy—and why these are non-negotiable for some
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Why so many women turn to entrepreneurship in their 40s, 50s, and beyond (with fresh statistics!)
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How personal style is a secret networking weapon and catalyst for engaging with the world
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The unique struggle (and privilege) of figuring out what you really want from work at this stage of life
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The power of community: you are not alone in your quest for reinvention!
Resources & Mentions:
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EvolveMe: an organization supporting midlife women re-entering the workforce
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Recent LinkedIn and demographic statistics on career breaks and entrepreneurship
Whether you're feeling invisible, itching for a new chapter, or struggling to make your experience relevant, you'll find humor, hope, and good company in this conversation. Be seen—by your community, and by yourself!
Share your story! Have you tried to return to traditional work and ended up an entrepreneur? Are you struggling with finding purpose or translating your experience? Email us or leave a review—your story could inspire a future episode!