It Girl with Bailey Taylor

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 looks like in her late 20s, why authenticity and kindness create lasting relevance, and how cooking, photography, and time away from social media help her feel grounded. Plus, she reveals her plans for a deeply personal coffee-table book and the quieter life she is building beyond the internet.
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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 she defines great personal style, the importance of buying pieces you truly love, her passion for telling bigger cultural stories through fashion, and the ultimate It Girl who has inspired her most.
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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, dealing with rejection, and finding the self-worth to stop settling for someone who makes you feel alone.
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Eva Meloche joins Bailey Taylor for her first podcast appearance to talk about growing up online, building boundaries with her audience, and learning how to keep parts of her life private while still sharing her world through YouTube. She opens up about finding her personal style through thrifting, Copenhagen fashion, and dressing for herself instead of chasing trends. Eva also talks about confidence, creativity, life in her 20s, her love of writing and Substack, and what’s next as she prepares for a new chapter in London.
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Lauren Chan joins Bailey for a conversation about building a career in fashion, finding confidence through defiance, and pushing the industry toward real inclusion. She looks back on her early days at Glamour, how The Devil Wears Prada shaped her dream of becoming a fashion editor, and what it felt like to realize she didn’t fit the traditional mold of the industry. Lauren also opens up about becoming the first out lesbian cover model for Sports Illustrated Swimsuit, using fashion as a form of queer self-expression, and why confidence now comes from doing things her own way. From secondhand shopping and emerging designers to body diversity, creative burnout, and the power of rest, Lauren shares what it means to build a life and career that actually feels aligned.
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