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 women in today’s job market

• The importance of meaningful work, creativity, and autonomy—and why these are non-negotiable for some

• Why so many women turn to entrepreneurship in their 40s, 50s, and beyond (with fresh statistics!)

• How personal style is a secret networking weapon and catalyst for engaging with the world

• The unique struggle (and privilege) of figuring out what you really want from work at this stage of life

• The power of community: you are not alone in your quest for reinvention!

Resources & Mentions:

• EvolveMe: an organization supporting midlife women re-entering the workforce

• 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!

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 roots in sculpture and theater design to building a slow fashion brand in San Francisco, Isobel shares the winding path that led to Bryr — and how the creation of her now-iconic “Chonk” shoe became a reclaiming of creative power.

Along the way, they unpack everything from Gen X fashion DNA, London vs. New York style archetypes, menopause visibility, and the radical power of not giving a f*ck. You’ll laugh, you’ll nod furiously, and you might measure yourself for a bathing suit by the end.

Guest: Isobel Schofield — Founder & Creative Director of Bryr

Topics Discussed:

• How menopause affects personal style and self-perception

• Gen X fashion identity and cultural attitude

• The cultural invisibility of older women and how we fight it

• Designing fashion as a feminist and creative act

• Reimagining aging as power, not decline

Where to find Isobel & Bryr:

• Website: bryrstudio.com

• Instagram: @bryrclogs

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 down why habits—not willpower—create change, how movement is a form of self-respect, and why no one ever achieved lasting transformation through shame.

Whether you’re feeling stuck, struggling with body image, or just ready to feel good again, this episode is for you.

Topics We Cover:

• Why self-hate doesn’t lead to body love

• Oonagh’s surprising path from fat activism to fitness

• The myth of willpower—and what actually works

• Why consistency beats intensity

• How strength training builds more than muscle—it builds identity

• Moving through menopause, burnout, and the “I’ve lost myself” feeling

• The truth about HIIT, cortisol, and over-40 fitness fears

• How fashion and fitness intersect as tools of empowerment

Resources Mentioned:

• Oonagh’s Free Fitness Resources

• Follow Oonagh on Instagram

• Oonagh’s podcast: Goals, Grit & Some Woo Woo Sh*t

💎 Guest: Marie McCarthy Founder of Fiat Lux and Rose Gold’s Piercing & Tattoo

In this episode, personal stylist Jennine Jacob and fashion journalist Kristen Philipkoski talk with Marie McCarthy, founder of fine jewelry store Fiat Lux and Rose Gold’s Piercing and Tattoo in San Francisco.

Marie shares how jewelry, tattoos, and piercings can be forms of power, rebellion, self-love, and pure fun—especially as we age. We discuss:

• Why women are getting piercings and tattoos later in life
• How style is about how you feel, not just how you look
• Using clothes and accessories as a language to communicate your mood, politics, or power
• How trends reflect society and why Marie ignores them
• Her personal style “rules” (hello, black skinny jeans forever)
• Why accessories are the secret to feeling cool in any outfit

Instagram:

Fiat Lux

Rose Gold’s

In this episode, personal stylist Jennine Jacob and fashion journalist Kristen Philipkoski talk with Danielle Bayard Jackson, friendship coach and author of Fighting for Our Friendships. They explore how what we wear can open the door to meaningful connections—and how friendships shape (and are shaped by) our personal style.

Danielle breaks down her three affinities framework—symmetry, support, and secrecy—revealing why women’s friendships are so powerful yet often fragile. She shares how style plays into first impressions and why dressing to express yourself authentically is a form of vulnerability that can actually fast-track finding your people.

They discuss:

• Why women’s friendships dissolve at a higher rate than men’s
• How wearing something “conversation-worthy” invites connection
• Why friendships sometimes fade after big life shifts
• Scripts for repairing friendship missteps
• The power of showing up as yourself, even if it risks rejection

Guest:

👭 Danielle Bayard Jackson – friendship educator, speaker, and author of Fighting for Our Friendships. Find her work at Better Female Friendships.

Listen if you want to:

✨ Feel more confident approaching new people ✨ Understand why friendships sometimes drift ✨ Explore how your style choices impact your social life ✨ Learn practical scripts to navigate common friendship pitfalls

This week on Closet Philosophy, we talk with Finnish street style archivist, photographer, and founder of the Gem app, Liisa Jokinen. Liisa has been documenting what people wear on the street for more than 20 years—and in doing so, she’s built a visual time capsule of personal expression, cultural shifts, and everyday creativity.

In this episode, we dig into:

• How second-hand shopping is freedom
• How clothing choices offer clues about identity, mood, and values
• What changed when she moved from Helsinki to New York
• How she developed the Gem app for vintage and secondhand shopping
• Why older women are some of the most exciting dressers
• And how to cultivate your own style voice over time

Liisa also shares her philosophy on dressing for yourself, what makes a great outfit, and why individuality—not trends—is the future of fashion.

Find Liisa:

• Street style archivist and founder of Gem
• Explore her photos: NYClooks.com
• Instagram: @nyclooks, @hellooks and @liisajokinen

Artist and former Apple exec Windy Chien joins Closet Philosophy this week to talk about how she left a high-profile tech job to follow a totally different thread—literally. Windy became world-renowned for her intricate and sculptural knot work, which she began exploring during her transformative project The Year of Knots.

In this conversation, we dive into the parallels between fiber and fashion, the deeper meaning of making things with your hands, and how creativity becomes a form of identity, discipline, and even rebellion.

We explore:

• How tying knots helped Windy reclaim authorship of her life
• The connection between personal style and artistic voice
• Why repetition is powerful—and not boring
• What it means to be a beginner on purpose
• What she loves about getting older (and no one tells you about)
• And why constraints can be the key to freedom

Windy also shares her take on aging, being a late bloomer, and how we don’t need to retire our style as we get older.

Find Windy:

• Artist & author of The Year of Knots
• See her work: windychien.com
• Follow her on Instagram: @windychien

In this episode of Closet Philosophy, we talk to stylist and luxury handbag designer Wale Sanni about what personal style really means—and it has little to do with what we wear. Wale shares how he went from sneakerhead to Saks stylist, why timeless style is about emotional connection, and how status, self-worth, and fashion are always intertwined.

We also dive deep into:

• Why people say they don’t care about status but they usually do
• Why quality isn’t just about fabric—it’s about how you care for your clothes
• The deeper meaning of the Walmart Birkin
• How self-love is the foundation of great style

Plus, Walle shares his take on what three things are actually worth investing in if you want a wardrobe that works and feels meaningful.

Find Wale:

• Stylist & co-founder of Nero Chicago
• Follow him on Instagram & TikTok: @stylebywale

This week, we sit down with the joyful and unapologetically bold influencer Manny Martins Carmen—a 61-year-old model, weightlifter, painter, and accidental content creator who encourages her followers to “age like a rebel.” What started as a creative outlet during COVID has become a movement of radical self-expression, vibrant style, and fearless aging.

We talk about dressing up for joy (even if you're just going to the optometrist), the healing power of movement, and how style can shift your mood and the energy of a whole room. Manny also opens up about recovering from a cancer diagnosis, competing in powerlifting, and applying for the Sports Illustrated Swimsuit Issue at 60+. Her message? Your joy is contagious—and it's never too late to be fully, loudly, you.

Topics We Cover:

• Why dressing up when you don’t feel like it is a powerful move
• How creative disciplines (like graphic design and abstract art) can shape personal style
• Using fashion as a form of emotional regulation
• What powerlifting taught Manny after cancer and injury
• Midlife confidence, visibility, and pushing back against patriarchal beauty standards
• The design principles behind good outfits—and good paintings
• The real reason she applied to the Sports Illustrated model search
• Why wearing a bigger size might be the most liberating thing you do all year

Follow Manny:

• Instagram: @mannyfashionstylist
• Art account: @mannymartinscarmen
• TikTok & YouTube: @mannymartinscarmen

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#ClosetPhilosophy #AgeLikeARebel #MannyMartinsCarmen #MidlifeStyle #PowerLiftingOver60 #StyleIsNotNeutral #AgingOutLoud #StyleAsJoy #NotYourDaughterStyle #WearTheSequins

In this mind-opening conversation, Véronique Hyland—features director at Elle magazine and author of the acclaimed book Dress Code: Unlocking Fashion from the New Look to Millennial Pink—helps us unpack the hidden forces shaping how we dress. From the myth of the “female gaze” to the politics of effortlessness, this episode asks big questions about power, gender, class, and whether we can ever truly dress just for ourselves.

We explore fashion as communication, resistance, and identity—and why “I don’t care what I wear” is almost always a lie. Plus, we get personal about aging, influence, cringe, and what it means to keep evolving your style in a culture that worships youth.

If you've ever stood in front of your closet wondering who you're getting dressed for—this one’s for you.

Topics We Cover:

• How she coined the term “Millennial pink”
• The commercialization of the female gaze
• Why effortlessness is its own kind of performance
• How personal style can be armor—and storytelling
• The privilege of “not caring” about fashion
• Why influencers burn out—and what’s changing in that world
• What fashion can learn from sports
• The difference between authentic style and aesthetic conformity
• Her journey from Juicy Couture to ELLE editor—and everything in between

Follow Véronique:

• Instagram: @veroniquehyland
• Column: Style Points on ELLE.com
• Book: Dress Code (available now)

💌 Subscribe to our Substack for deeper dives, style essays, and behind-the-scenes content.

#ClosetPhilosophy #DressCodeBook #VeroniqueHyland #PersonalStyle #FashionPolitics #FemaleGaze #EffortlessStyle #MidlifeFashion #NotInvisible #AgingOutLoud #StyleAsResistance