Closet Philosophy – Details, episodes & analysis

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

Bestselling author and organizing expert Shira Gill joins us this week. Her work goes far beyond decluttering—Shira believes that organizing is not about perfection, it's about creating space for what actually matters.

We talk about:

• Why most people don’t have an organizing problem—they have a volume problem
• What to do with clothes that no longer fit but are hard to let go of
• How to make getting dressed easy and empowering
• The emotional cost of hanging on to “someday” clothes
• Why dressing with intention is a form of self-trust and self-respect
• The myth of “effortless” style—and how to find your own version of it

Plus, Shira shares her go-to closet edit tip, how she broke up with uncomfortable jeans, and why your clothes might be saying more than you think.

🎧 Tune in and learn how editing your closet can help you edit your life!

In this episode of Closet Philosophy, we meet Sophia Hall, the vibrant force behind @makegood on Instagram. Sophia is a secondhand style expert who turned childhood thrift store adventures into a thriving online business serving women of all sizes—especially those who often feel ignored by the fashion industry.

We talk about:

• Growing up as the youngest of eight and learning to dress for survival, identity, and joy
• Why the fashion industry still isn’t cutting it for plus-size folks—and how secondhand can offer freedom and power
• Sophia’s honest, empathetic approach to styling clients, from measurements to mindset shifts
• The magic of her Instagram Live sales, where community, confidence, and clothes come together
• How women of all ages and sizes can reclaim comfort, color, and self-expression—even in a world that tells us to shrink

Plus: unexpected styling hacks, Billie Eilish shoutouts, the secret weapon of the men’s section, and why one of her customers once watched a live sale from the front row of a Botticelli concert (yes, really).

✨ Subscribe now so you don’t miss next week’s episode—because we’re just getting started unpacking what style can really do.

💚 Find Sophia on Instagram: @makegood

💚 Follow us on Substack: Closet Philosophy

💚 Join the conversation on Instagram: @closet.philosophy

What if lipstick could change more than your look—what if it could change the narrative?

This week on Closet Philosophy, we’re joined by powerhouse founder Jenn Harper, the visionary behind Cheekbone Beauty—one of the first Indigenous-owned beauty brands in North America. Jenn shares how a dream in early sobriety led to a mission-driven brand that’s redefining what beauty means, who it’s for, and what it’s made of.

We dive into:

• The dream that started it all: three laughing Native girls with lip gloss and a spark of possibility
• How generational trauma—and healing—shaped Jenn’s identity, sobriety, and purpose
• The power of representation for Indigenous people in the beauty industry
• Why not knowing your full history doesn’t mean you don’t belong
• Sustainability beyond buzzwords—what it really means to build a brand with the next seven generations in mind
• Veganism, cultural nuance, and honoring traditional lifeways
• The story behind Cheekbone’s stunning lipstick names (spoiler: every shade is a language lesson)
• And a sneak peek at a powerful red lipstick collab you’ll definitely want on your lips—and in your life

Jenn also shares how her Indigenous values shape every decision—from the supply chain to the pigments—and why sustainability, transparency, and community care are non-negotiables.

If you’ve ever wondered how to live your values out loud, or how to turn personal pain into world-shifting power, this episode is your roadmap.

✨ Subscribe now so you don’t miss upcoming episodes—and keep an eye out for that red lipstick drop.

💚 Find Cheekbone Beauty on Instagram: @cheekbonebeauty

💚 Follow us on Substack: Closet Philosophy

💚 Join the conversation on Instagram: @closet.philosophy

What if the coolest girl in the room was 64 and completely unbothered?

This week on Closet Philosophy, we’re talking with the one and only Heidi Clements—a writer, content creator, and style icon with 1.8 million followers who has become a voice of radical authenticity for women of every age.

Heidi shares how she went from TV writer to unexpected TikTok star in her 60s, why getting dressed is both a political act and a personal therapy session, and how to finally stop dressing for the male gaze—or anyone else’s expectations.

We get into:

• Heidi’s surprising path to online influence (spoiler: it starts with pizza 🍕)
• Dressing without shame, rules, or apology
• The myth of the “cool girl” and why being unbothered is the new sexy
• Why your neck, your stomach rolls, and your closet are not problems to fix
• Finding your power in midlife—and giving yourself permission to be loud, visible, and real
• The magic of saying “f*ck off” (lovingly)

This is a conversation about more than personal style—it’s about personal freedom. Whether you’re navigating midlife, recovering from people-pleasing, or just want to feel a little braver in your own skin, this episode is for you.

📌 Plus: Heidi’s best accidental outfit formulas, why she films in her bathroom, and what happens when you accidentally flash your... well, just listen.

✨ Subscribe now so you don’t miss next week’s episode—because we’re just getting started unpacking what style can really do.

💚 Find Heidi on Instagram: @welcometoheidi

💚 Find Heidi on TikTok: @welcometoheidi

💚 Follow us on Substack: Closet Philosophy

💚 Join the conversation on Instagram: @closet.philosophy

Welcome to Closet Philosophy, the podcast that believes what you wear is never just about clothes.

In our preview episode, personal stylist Jennine and fashion writer Kristen share how this podcast was born—from a serendipitous interview to an ongoing conversation about the power of personal style. Together, they unpack why midlife is a moment of transformation, not disappearance—and how clothing can be a tool for confidence, self-expression, and resistance.

We dive into:

• The story behind Closet Philosophy
• Why dressing powerfully is a political act—especially for women in midlife
• Jennine’s Venn diagram of Quality, Memorability, and Authenticity
• A client success story that proves a red suit can change your life
• Why quiet luxury isn’t always as “aspirational” as it seems
• The real reason you don’t need a personal shopper—you need personal agency
• And what AI, tax accountants, and The Jetsons have to do with getting dressed

This isn’t a podcast about fashion. It’s a podcast about meaning. About how we show up in the world. And how we take up space—on purpose.

✨ Subscribe now so you don’t miss Episode 1, where we’ll start digging even deeper into the psychology and politics of personal style.

💚 Follow us on Substack: Closet Philosophy

💚 Join the conversation on Instagram: @closet.philosophy

💎 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