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It Girl with Bailey Taylor

It Girl with Bailey Taylor

iHeartPodcasts 17 Episodes Aug 19, 2026

Through intimate, unfiltered conversations with fashion editors, celebrities, founders, and cultural leaders, It Girl with Bailey Taylor captures both the glamour and the reality of life in the public eye. The podcast expands the popular online series into long-form storytelling, creating space to explore ambition, visibility, pressure, and the struggles that come with being an “it girl” today—beyond the highlight reel.

Episodes

Mia Calabrese: NYC Dating, Red Flags & Why Ambitious Women Should Stop Settling
Mia Calabrese: NYC Dating, Red Flags & Why Ambitious Women Should Stop Settling Aug 19, 2026 2173 Mia Calabrese joins Bailey for a candid conversation about the realities of dating in New York City, why situationships have become so normalized and what she’s learned about dating more intentionally. They get into whether success makes dating harder for women, men who resent ambitious partners, splitting the bill and why you should never have to question whether someone actually likes you.
Claudia & Gabby: Co-Founding Vin., Good Taste & Building a Fashion Brand
Claudia & Gabby: Co-Founding Vin., Good Taste & Building a Fashion Brand Aug 12, 2026 2924 Claudia Li Johnson and Gabby Kono-Abdi, co-founders of Vin, join Bailey to talk about turning their shared love of vintage and statement accessories into a fast-growing fashion brand. They share how their iconic Fishy bag came to life, why launching before everything was perfect worked in their favor, and how intentional gifting helped get Vin into the right hands. They also get into running a bus
Charlotte Palermino: Dieux Skin, Beauty Myths & Building a Brand That Lasts
Charlotte Palermino: Dieux Skin, Beauty Myths & Building a Brand That Lasts Aug 5, 2026 2707 Dieux Skin founder Charlotte Palermino joins Bailey Taylor to talk about building one of the most trusted skincare brands by leading with science, evidence, and transparency. She opens up about leaving the corporate world, why she wanted Dieux to be more than another trendy beauty brand, and how distrust in healthcare and “clean beauty” culture can radicalize women online. Charlotte al
Taylor Quitara: Art, Personal Style & the Power of Being a Little Weird
Taylor Quitara: Art, Personal Style & the Power of Being a Little Weird Jul 29, 2026 3295 Artist and NYC cool girl Taylor Quitara joins Bailey to talk about building a creative life, developing your personal style and learning to embrace the things that make you different. Taylor shares how she turned painting into a career, used social media to get her work discovered and learned to tune out other people’s opinions. They also get into vintage shopping, developing your taste, esc
Levi Sebree: Dating Without Rules, Friendship Green Flags & Breaking Into Fashion
Levi Sebree: Dating Without Rules, Friendship Green Flags & Breaking Into Fashion Jul 22, 2026 2823 Levi Sebree is back for a candid catch-up filled with dating confessions, friendship advice and the reality of building a career in fashion. She and Bailey compare New York and Los Angeles dating, debate underrated green flags and explain why the usual relationship rules rarely work. Levi also shares how she went from cold-emailing hundreds of fashion companies to working with major brands, provin
Listener Q&A: How to Build Confidence, Know Your Worth & Become Unstoppable
Listener Q&A: How to Build Confidence, Know Your Worth & Become Unstoppable Jul 15, 2026 2718 In this solo episode, Bailey answers listener questions about building confidence, recognizing your worth and becoming the version of yourself you want to be. She shares practical advice for moving past self-doubt, rebuilding your self-esteem and refusing to let insecurity keep you from opportunities, relationships or new experiences. Bailey also explains why confidence starts with your mindset, h
Iris Kendall: Love Island, Dating Lessons & Boho Chic Style
Iris Kendall: Love Island, Dating Lessons & Boho Chic Style Jul 8, 2026 1929 Iris Kendall joins Bailey Taylor for a dreamy conversation about life after Love Island, dating in your 20s, and finding your style era. She opens up about what really happens behind the scenes of reality TV, how the experience shaped her confidence, and the relationship lessons she’s taking with her now. Iris also gets into long distance love, money advice every woman should hear, building
Violetta Komyshan: Ballet-Core, Color Analysis & Curating Your Life
Violetta Komyshan: Ballet-Core, Color Analysis & Curating Your Life Jul 1, 2026 2860 Violetta Komyshan joins Bailey Taylor to talk about the discipline, beauty, and reality of life as a ballerina. She opens up about growing up in New York, building a career in dance, and how ballet shaped her confidence, femininity, and effortless personal style. Violetta shares why color analysis changed the way she gets dressed, how she curates a more intentional closet, and why vintage ’9
Chandler Guttersen: The Story Behind Vintage Grace & Finding Personal Style
Chandler Guttersen: The Story Behind Vintage Grace & Finding Personal Style Jun 24, 2026 2775 Vintage Grace founder Chandler Guttersen joins Bailey to share the personal story behind the name of her beloved New York vintage destination. Chandler reveals how Grace—her first name and a tribute to both of her grandmothers—became the perfect reflection of the timeless, elegant, and welcoming brand she wanted to build. She also opens up about growing up on a Colorado cattle ranch, w
Olivia Joan: Her Grandmother’s Closet, Whimsical Style & Life Beyond the Internet
Olivia Joan: Her Grandmother’s Closet, Whimsical Style & Life Beyond the Internet Jun 17, 2026 2559 Content creator and photographer Olivia Joan joins Bailey to talk about how sharing her grandmother’s extraordinary wardrobe online unexpectedly changed her life and career. She opens up about honoring that legacy while rediscovering her own personal style, embracing whimsical fashion, and learning to say no to opportunities that leave her feeling drained. Olivia also shares what confidence
Leah Faye Cooper: Vogue, Fashion Criticism & What Makes Great Style
Leah Faye Cooper: Vogue, Fashion Criticism & What Makes Great Style Jun 10, 2026 3371 Fashion writer and editor Leah Faye Cooper joins Bailey to talk about her journey from teaching high school in Houston to building a career in fashion journalism and landing at Vogue. She opens up about the years of rejection, freelancing, and ambition that shaped her path, plus why strong writing and thoughtful criticism still matter in an industry that has changed so much. Leah also shares how s
The It Girl Guide to Breakups, Situationships & Choosing Yourself
The It Girl Guide to Breakups, Situationships & Choosing Yourself Jun 3, 2026 2532 In her first solo episode of It Girl, Bailey answers listener questions about breakups, situationships, dating again, and learning when it is finally time to walk away. She opens up about heartbreak, toxic relationships, chasing people who do not choose you back, and why healing does not always happen on anyone else’s timeline. Bailey also gets honest about being single, dating in New York,

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