Amy Astley on Working Alongside Anna Wintour and Building Brands

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This week on the show, editor-in-chief of Architectural Digest Amy Astley reflects on her path from aspiring ballerina to journalist to leading some of the most influential publications in fashion and design, including Architectural Digest and Teen Vogue. She opens up working alongside Anna Wintour, navigating high-pressure creative environments, learning to trust her instincts, and her thoughts on what it truly means to be a “taste maker.” Together, Maria and Amy talk about perfectionism, ambition, mentorship, self-doubt, and the pressure women often feel to prove themselves in leadership roles. They also discuss taste, storytelling, social media, creative risk-taking, and why curiosity may be the most important skill of all. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. ⁠⁠Listen to every episode on your favorite podcast platform⁠⁠ ⁠⁠Follow Maria on Instagram ⁠⁠ ⁠⁠Follow Maria on X⁠⁠ ⁠⁠Follow Pretty Tough on Instagram⁠⁠ ⁠⁠Subscribe to Pretty Tough on Substack 00:00:00 Intro: Redefining Taste in a Borderless World 00:02:18 The "Dutiful Daughter" Archetype in Business 00:04:00 Ballet Beginnings: Learning Discipline and Letting Go 00:08:24 Career Lessons from Anna Wintour 00:10:04 The Power of Saying "Yes" and Taking Opportunities 00:12:44 Transforming Architectural Digest 00:14:14 The Mission Behind Teen Vogue 00:17:15 The Strategy Behind Magazine Covers 00:23:18 The Digital Evolution of Legacy Media 00:28:48 Pretty Tough Tips: Visualization for Success 00:33:55 The "Open Door" Series: Connecting Through Content 00:43:24 Facing the Future: AI in Publishing 00:51:57 Moving Beyond the "Tastemaker" Label 00:55:00 Integrating Personal Life and Professional Practice 01:00:17 NYC Design Recommendations 01:04:12 Pretty Tough Questions: Lessons, Routines, and Perfectionism Learn more about your ad choices. Visit podcastchoices.com/adchoices