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

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

#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

In this deeply honest and empowering episode, we talk to Erin Wallace, head of marketing at ModeSens, and formerly of ThredUp and Crossroads Trading. She’s a fashion marketing powerhouse, creative leader, and style icon in her own right. Erin shares how her personal style became her superpower in the workplace, why she didn’t truly find “her look” until her late 30s, and how fashion helped her step into leadership after a major life transition.

We also get real about what happens when your body changes in midlife, why some outfits feel like home and others feel like costumes, and what it means to truly feel like yourself in your clothes.

If you’ve ever questioned whether you can be taken seriously while dressing boldly—or felt like your closet was full of pieces for someone you used to be—this one’s for you.

We talk about:

• How style can be a “positive weapon” in your career
• The link between confidence, clothing, and authenticity
• What to do when your go-to jeans stop fitting during peri- and post- menopause
• The internal feeling of knowing when an outfit is “you”
• Erin’s advice for anyone second-guessing their bold style in a boardroom
• Her go-to styling tricks (hint: it starts with rolling up your sleeves)
• Why you should find your own pink plaid suit

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

#ClosetPhilosophy #AuthenticStyle #MidlifeStyle #FashionAndLeadership #MenopauseStyle #SustainableStyle #AgingOutLoud

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