The Business of Fashion Podcast

Episode: How Willa Bennett Is Reimagining Magazines for a Social-First Generation
Date: January 16, 2026
Host: Imran Ahmed, Founder & CEO, The Business of Fashion
Guest: Willa Bennett, Editor-in-Chief of Cosmopolitan and Seventeen

Episode Overview

This episode features Imran Ahmed in conversation with Willa Bennett, the editor-in-chief spearheading the creative and commercial reimagination of legacy magazines Cosmopolitan and Seventeen. The discussion delves into Willa’s unconventional career path, her insights on youth culture and media consumption, the current challenges facing legacy media brands, and her vision for curating content that resonates with a "social-first," highly discerning generation.

Key Discussion Points & Insights

Willa Bennett’s Early Influences and Media Career

• Background & Formative Years

  • Willa grew up in Los Angeles with early interests in fashion, though she couldn’t sew and didn’t see herself in marketing. Her love for magazine culture started young.
  • "I was really the one in my friends group who was really curious about fashion. ... I saw these magazines and I was like, wow. It really combines my love of fashion and my curiosity for fashion with writing." (Willa Bennett, 04:00)
  • She studied journalism at Sarah Lawrence, where she noticed a disconnect between traditional journalism education and the emerging realities of digital and social-first fashion media.
  • Senior thesis: Spent a month in a middle school researching how teens engage with media like Teen Vogue and brands such as Glossier, uncovering the early significance of platforms like Snapchat and Instagram.

• Breaking Into Magazines and Early Innovation

  • Landed her first job at Seventeen through a cold email, where her initial role included managing the brand's CMS and spearheading some of their first Instagram posts. She notes legacy brands were slow to take social media seriously at the time (2013).
  • "At that time ... none of these magazines were taking Instagram quite as seriously." (Willa Bennett, 05:19)
  • Her on-the-ground experience in fashion media quickly revealed a surprising disconnect between in-person fashion experiences and the performative, content-driven mindset prevalent among industry professionals.

From Entry Level to Industry Recognition

• Finding Her Voice at GQ and High Snobiety

  • Bennett’s career progressed through stints at Bustle Digital Group, GQ, and High Snobiety, where she found her editorial "voice"—especially in men’s fashion.
  • Significant moments included publishing feature covers such as Billie Eilish for High Snobiety and Brenda Song/Macaulay Culkin for Cosmo, which blended personal storytelling and fashion, and helped redefine what magazine covers could mean.

• The Billie Eilish High Snobiety Cover

  • "It was so intuitive... What signaled to me was successful about that editorial ... was we put her in Simone Rocha ... she wore Simone Rocha to the Met gala ... because of that High Snobiety cover." (Willa Bennett, 14:40)

Redefining Youth Culture and Media’s Role

• The Need for Real Curation

  • Young audiences, inundated with content, crave "real curation, not performative curation, and real taste."
  • "This generation actually has access to so much online. But that also means that ... there is a real hunger for curation and real curation, not performative curation, and real taste." (Willa Bennett, 01:08, 16:46)
  • Willa emphasizes the importance of a strong editorial point-of-view and authority, noting legacy media's capacity to act as trusted taste-makers amid the “cacophony of voices” on social media.

• Legacy Brands’ Purpose in a Social-First Era

  • Legacy titles like Cosmo and Seventeen hold enduring appeal because they pair trusted editorial authority with a clear, focused voice—something that transcends the current influencer-saturated landscape.
  • "What I always say is we curate the influencers: it's about having the right type of influencers." (Willa Bennett, 22:22)

• Luxury Brands & Youth: A Nuanced Relationship

  • While luxury isn’t for everyone, micro-communities of young people are still actively engaging with luxury (i.e., Coach’s Tabby bag as a viral example).
  • Smart, culturally aware partnerships—such as Cosmo’s editorial work with emerging talent from K-pop and TV—help legacy brands stay relevant and aspirational.

Navigating the Modern Media Landscape

• Editorial vs. Commercial Divide

  • There’s growing integration between editorial and commercial teams, but success comes from authentic, valuable brand partnerships that align with the magazine’s voice and audience.
  • "I do still say no to advertisers. If it's not a right fit, it's not a right fit." (Willa Bennett, 33:47)
  • She gives examples of successful brand collaborations (like Coach and ELF Cosmetics) and the importance of maintaining editorial standards.

• Embracing Platforms and Finding Your Voice

  • Advice for young journalists: Use all available platforms to experiment, build, and share your distinct voice.
  • "Use all the platforms now ... get on Substack, use your Instagram, use your Twitter ... why else would you follow someone?" (Willa Bennett, 35:55)
  • Substack and similar platforms allow for rapid dissemination of new voices and ideas, but standing out requires consistent, original, and authoritative content.

• Magazine Covers and Editorials: The Return of Creativity

  • Willa observes a renewed emphasis on innovative, high-production-value editorial projects as brands move away from the relentless chase for digital scale at the expense of creative quality.
  • "We're seeing, like, real editorials again. ... Now it's like, we all get to really return to, like, the power of editorials." (Willa Bennett, 29:43)

Notable Quotes & Memorable Moments

• On the BOF 500 Gala:
  "That room is just so surreal. ... The juxtapositions of all these different voices is just. There's no other room like it. ... I told Simone Rocha that I would love for her to make my wedding dress one day, so I might get a wedding dress out of it." (Willa Bennett, 02:47)

• On Fashion Shows & Authenticity:
  "[Fashion shows] ... it felt like surprising to me that people were just there to take content. And this is coming from someone who, like, loves social media more than life itself. ... Dries last show ... I looked around and, like, truly no one was on their phone. ... It was just this moment where I was like, wow, like, I made it to this Dries show. Like, it was so, so, so special." (Willa Bennett, 08:45–10:12)

• On the Importance of Editorial Authority:
  "There’s a real need for young people to have some sort of, like, authoritative voice, whether that be in fashion or in their love lives. And I think that is something that Cosmo does do really well..." (Willa Bennett, 22:22)

• On Creating Standout Content:
  "You can stand out, you can break through again. You just need to make sure it's, like, special and real." (Willa Bennett, 41:55)

Important Segment Timestamps

• Introduction and Willa's Media Background – 00:04 to 07:15
• First Job at Seventeen & Early Social Media Editing – 07:16 to 10:10
• Breakthrough Moments: Billie Eilish and Editorial Voice – 10:48 to 15:44
• Defining Youth Culture & Media’s Role – 16:20 to 22:22
• Legacy Brands vs. Influencers – 22:22 to 24:41
• Media Disruption & Revival of Editorial Creativity – 29:00 to 31:44
• Commercial Partnerships and Editorial Integrity – 32:16 to 35:20
• Advice for New Journalists & Finding Your Voice – 35:55 to 39:19
• Standing Out in a Noisy Digital World – 41:05 to 42:17

Tone and Closing Thoughts

The tone throughout is warm, candid, and deeply engaged with both the culture and business of fashion media. Willa and Imran speak as industry insiders and passionate observers, oscillating between big-picture analysis and personal anecdotes. Willa’s approach is optimistic, focused on the essential role of voice, curation, and genuine connection with audiences in the evolving landscape.

"Cosmo didn’t need a rebrand. ... It just really needed to refocus. And I think the last year and a half now have really been about refocusing, refining, infusing voice." (Willa Bennett, 24:41)

Summary by [Podcast Summarizer AI, 2024]