Mia Calabrese: NYC Dating, Red Flags & Why Ambitious Women Should Stop Settling

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, s…

Claudia & Gabby: Co-Founding Vin., Good Taste & Building a Fashion Brand

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 fav…

Charlotte Palermino: Dieux Skin, Beauty Myths & Building a Brand That Lasts

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 di…

Taylor Quitara: Art, Personal Style & the Power of Being a Little Weird

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 tu…

Levi Sebree: Dating Without Rules, Friendship Green Flags & Breaking Into Fashion

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 shar…

Listener Q&A: How to Build Confidence, Know Your Worth & Become Unstoppable

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 opportuniti…

Iris Kendall: Love Island, Dating Lessons & Boho Chic Style

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 h…

Violetta Komyshan: Ballet-Core, Color Analysis & Curating Your Life

Violetta Komyshanjoins 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 c…

Chandler Guttersen: The Story Behind Vintage Grace & Finding Personal Style

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 br…

Olivia Joan: Her Grandmother’s Closet, Whimsical Style & Life Beyond the Internet

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…