Navigating A New Era of Virality, Rage Bait, and Gen Z Content with Cosmopolitan's Editor-in-Chief

0:01Hey, everyone. It's Liv Perez, and welcome back to another episode of Let's Get Dressed. Today's guest is actually someone who I have known since we were teenagers growing up in Los Angeles, but she is also one of the most powerful people shaping modern media today. And that's because before she was even 30 years old, Willa Bennett took over not one, but two of the most iconic magazines in media, Cosmopolitan and Seventeen. She stepped into that role at a moment when legacy media is definitely in flux and basically being declared dead. Attention spans are shrinking and culture is moving at the speed of light on the internet.

0:38So I wanted to ask her, what does it actually look like to run a publication in 2026? We sat down to talk about viral content, celebrity culture, analytics, and what it really means to build trust with an audience today. We also talk about controversial covers like the Timothee Chalamet Vaux cover, AI dating, whether rage bait in media is real, and why a story versus just star power is really what's driving culture right now. I love this conversation. And if you guys loved it too, make sure you go leave us a review on Apple Podcasts and Spotify as well. Let's go get dressed with Willa Bennett.

1:13Willa Bennett: Welcome to the pod. Thank you. I'm so excited. I've known you literally since middle school. Yes. Okay. You're right. Is that true? It's like seventh Ninth grade? You were ninth. I was eighth, maybe. Oh, I forget where you're apart. I met you in ninth grade. I was in middle school. Yes. Where were you in middle school again? Oakwood. Oh, I forget. Oakwood was in middle school. You were at Buckley. I was at Buckley my whole life. That's amazing. So yeah, you were around, but like that is so, so, so. I've known you for a long time. I know. And it's been so cool to watch you. And I feel like you were really early to the podcasting, which is so cool.

1:45Thanks. Yeah. We've had the pod for like five years. It's amazing. I'm so happy. And I'm so happy to finally have you here. This is the perfect time. Yeah, I'm so glad. How has your fashion week been? What are you looking forward to in fashion month?

1:55Willa Bennett: Oh, that's a good question. I really loved Proenza yesterday. I really love Tori always. You were there. Obviously, Coach. I actually, it was a really good collection, I thought. And like, I felt like this season, the clothes, I really will be wearing some of it in a really real way. I think last season, I really appreciated it, but it wasn't like something I would necessarily wear. And then this season, I was like, okay, they're like these shorts I really like that were like suit pants, really good colors. It actually reminded me of like the season of Prada that like had the collared shirts. Like, I don't know.

2:27Willa Bennett: There was a lot going for it. Are you going to Europe? I'm not going to Europe. Unfortunately, we have like so many shoots that this season I will not be there. But I am looking forward to a lot of the shoots we're having. And I don't know. I'm in this like phase right now where I really, really, really love to be on set. We're just shooting a digital cover in Puerto Rico and like I wrote the story but I also was like you know in the weeds talking to the manager like getting different shots like I think that is important as a leader to like really be able to do different parts of people's jobs and like be seen as part of it with them and not you know not like against them or better than them I really learned that from Will Welsh honestly like I think I remember working under him and he would like come and sit down next to me at my desk at GQ and like talk to me about like different captions.

3:16Willa Bennett: And like, it just meant so much to me. And like 20 minutes with him would have like made me think so differently about social. So I really try as much as I can to be in the weeds. I think you have to do all the roles before you get to the one that you're at so you can understand them better. That is something that I feel is so important. I'm a big advocate for not going in the straight line. Yeah. And I think more and more like young people are redefining the workforce in such a cool, interesting way and like in a way that is genuinely inspiring to me. And I want people to feel like even within their role, they can try things and make mistakes.

3:51Willa Bennett: And like, you know, so I think it's helpful if like you see a leader being like, oh, you know, it's the Grammys. I'll jump in and write some captions or I'll jump in and write this piece or I'll run to set and like get water. Like, you know, it's all part of it. And I think you could tell in the work. Like, I think you can really tell in my iteration of Cosmo, like we're having fun. Yes, deeply. And like, that is sick to me. I'm really curious. Just even going off of that, you are in your early 30s. Yeah. You run two magazines, Cosmopolitan and Seventeen. And I would love to hear from you how you've been able to hone in on your editorial voice.

4:33Like, what makes it fun for you? Like what spins the wheels every day? But also you're in an industry where this is like legacy media. Like there are people who have been steering the ship for a long time before you. So how have you figured out what your voice is in both of those ways to make sure that you're heard and all of that is validated?

4:53Willa Bennett: Yeah, I think what is so cool about both of those brands is like I was legitimately like a fan growing up. So it's not like they were these like unattainable magazines that, you know, maybe spoke to an audience or a specific subset of fashion that was like aspirational. Like it was like something that I relied on to like understand who I was, both of them in very different ways. I try not to group them together. Like 17 is really like I say it all starts at 17. It's really documenting what it's like to be a teenager right now. And then Cosmo really is about love and relationships. And I think what's so cool about both of them is like I was legitimately a fan.

5:34Willa Bennett: I'm still legitimately a fan. And like I am the demographic. So there's a lot of moments where I'm like going through something and I'm like, what is the content that would actually be helpful? And I think that is where the wheels kind of spin. But I also feel very grateful in this time of, you know, so much change in media to like have two incredible brands that have such a legacy. I think it's really fun to play in that. I mean, I think of our 60th anniversary issue with Margaret Qualley and like it was so important to us that we were like honoring what Helen had built at Cosmo. And even in the most recent issue, which I'm sure we'll get into, like it really was about honing in on these like moments of Cosmo and these this narrative that we've had and this legacy we've built.

6:17Willa Bennett: And like, you know, not shying away from mistakes or controversy, but really like honoring what Cosmo was. And so I think having a legacy is really, really, really special and like not something to shy away from. And I don't think it's always been true. Like I think sometimes, you know, there have been a media where like tons of startups are emerging and it just thinks quicker than corporations. But right now, I think there is something that I really trust about legacy media and like really, you know, I there's so much information that it's like if I'm going through something in my life, like I want to hear from a trusted source.

6:49Willa Bennett: and I think having that history is an asset. I would love to know what the moment that you got the job felt like. Like what was the enormity of that moment? No one's ever asked me that. It's interesting. So I had to give this presentation to a bunch of people in a room and I gave like my pitch of what I would do with the brand and I left Hearst Tower and I was like walking to my apartment in the West Village and I started sobbing and I like couldn't really understand why. Like it was one of those things that I was just like started. I like burst out into tears because I was like, wow, this is feels so right.

7:30Willa Bennett: But like, I don't even know what's going to happen. Like I hadn't even gotten the job yet, but I just was like, it felt like so, so, so right in like a way I don't think I've ever felt in my career. And there's a lot of things I'm proud of. And there were a lot of moments of like pieces I wrote or, you know, meetings I had taken or advertisers I brought in in my previous roles that like maybe from the outside were like, wow, like that's so impressive. But that moment, like the actual work of thinking about how I was someone that had had the ideas to bring back and the like editorial perspective to like bring something back to a generation that like is so needed.

8:05Willa Bennett: That is like what overwhelmed me. And I like have chills thinking about it again. And that was kind of the moment where I was like, wow, this would be amazing. And it was so big that I almost like didn't have a moment to have like self-doubt. It was like this big feeling was kind of all encompassing. And then eventually when I started, obviously like the actual feeling of like, okay, what the heck now? Like, how are we going to do this? How are we going to build this? And, you know, you kind of get in the weeds and you start to see things that you can change, you can't change. And the reason that things are the way they are, that was like a whole different feeling.

8:37Willa Bennett: But the big feeling that has always been through this era of my life has been like, I really deeply believe that people need a magazine like Cosmo or a brand like Cosmo in the world. And so what can we do to make it last forever and be there and you can trust us? The reason I asked that question is because as the viewer, when the news dropped, it felt like an enormous moment as a consumer of content. Like even I think a thing in fashion now is like, do I think that a lot of the people that run a lot of fashion corporations and big brands are the actual demographic of the people they're talking to.

9:13And so are those decisions being made in not so much in their best interest, but like, are we all on the same page? And for the first time, I think when you were announced, I was like, oh, that's the same page. Like that makes sense. Like she is living the experience of the people she's creating content for.

9:31Willa Bennett: And like, I think I love what Alex Cooper has done. And I think that she, especially in love and relationships, I think fashion, wait a sec, but like what she's done in love and relationships is like actually so inspiring and so admirable. But like, I do think there's a subset of younger audience that like they are seeing stuff on the internet and like it is not safe to just be listening to everything out there. I mean, I get served wild stuff sometimes and I'm like, I was like 11 or 12, even like 14, 15. If I was the age we met, like I would have like my life would be very different. Like I would think so differently about the world.

10:08Willa Bennett: I think so differently about myself. So there is that responsibility. And I think there there is that that always hangs over me like this is a responsibility to like really serve this audience. And no one I think is really doing it in this way, especially coming from a platform like Cosmo. The fashion thing is really interesting you say that because I've been thinking about this a lot. Like I think, you know, we just saw all these new debuts and now it's like hitting the stores and we're seeing actually how it's being crystallized. And it reminds me, it just is such a specific time. Like we've never seen such unprecedented like change at once.

10:42Willa Bennett: And there's part of me that's like so excited about it. And then the other part of me is like, who has the answers? Right. And who's steering that ship? And there's no one, which I really try to look at as like an opportunity. Everyone's trying to figure it out. Everyone's trying to figure out what this means, where we're going to be getting content, where we're not going to be getting content, which platforms, which billionaires are going to own what. Like there's a lot going on and I think again to have a brand that's like so clear on what it is and what it stands for in a market where there's such a clear brand proposition is just so lucky and I feel lucky every day.

11:16I would love to know what your actual like day-to-day is like now as an editor-in-chief. We both grew up on the Devil Wears Prada and the Hills and the Teen Vogue and I think the idea of what we think of an editor-in-chief, our perception of it is probably nowhere near what it's like today in 2026. So what is it like for you today?

11:34Willa Bennett: Yeah, it's a lot of meetings, a lot of back and forth, a lot of meeting with talent, photographers, writers, finding stories. I would say it's a lot like it's a lot of like early morning coffees and like drinks, dinner type. And then during the day, I really am in the office. I like to be with my team. Like even when I'm traveling for a while, I feel like I should be back in the office. I do have this draw to being with the team because I think so much comes from that. My favorite meeting, though, is Wednesdays. We have office hours, which a leadership style I've actually inherited from Will also, where he would gather the team every single Wednesday.

12:15Willa Bennett: It was like 4 p.m. It still burned into my brain like years ago. And we do it at Cosmo. And I also did it at High Snobiety where I used to run. And it's basically like we come together and there's, you know, some weeks we tell ideas, other weeks we have guest speakers, different things. But I just I really do make the case for like carving out regular time to be together as a staff. And like it look it's hard, like especially when you're running, you know, a news team or, you know, people who are so reactive to the news, a social team like it's hard to be like, OK, let's just all gather. but it is always worth it.

12:50And I think it's important to have time where everyone can just

12:54Willa Bennett: be on the same page, even if it's like something as simple as we're going to talk about Valentine's Day next year. You know, like sometimes it's like super far in advance. Sometimes it's walking through an issue or going through a video series. But I just think it's important to all be in the same room and be like, we work for the same brand and we all want the same thing. Today's episode is presented by Depop. If you know me, you know I am big on a closet reset. I genuinely think that when your closet feels organized, your brain and life does too. So how many things are in your closet right now that you have loved when you bought them?

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14:15Willa Bennett: I can't help but think of all these rooms that you've just mentioned that you've been in where you are. You're probably one of the younger people in the room in these 4 p.m. Wednesday meetings. I think for me, I was just very I was more like it was more like I was the online one, to be honest, right, where I was like, hey, what about the song driver's license? like right height of it popping off and people being like, what are you talking about? I'm like, guys, this is the number one song in the world. That is such a weird, you know, I saw I saw a TikTok the other day that deeply resonated with me.

14:49And it was like, if you are someone born in the 90s, your role in your in this lifetime is to be the bridge and translator between the offline and online world. Like you grew up in a time where you did not have phones and now you do have phones and you've adapted and you've figured it out, but you are tasked with this responsibility of explaining that to people, like explaining how to be offline and be online. I had a job in my early 20s and I was like brought in as like the young 22 year old girl who was to like advocate for like the digital influencers, new agey stuff. And I was first 100 % the youngest person in the company.

15:28And no one listened to me.

15:31Willa Bennett: That's like how it goes though. Like, right? Like, how do you overcome that? How do you do it? I just like, I always lived on the internet. Like, I just did. Like, I was on LiveJournal. I was obsessed with fan fiction. Like, I loved magazines because I loved like the discourse on Tumblr. So it was like, so it is so innate to me. You were the Tumblr girl growing up. Just everybody who needs to know like the LA lore, you were the Tumblr girl. I did like randomly have a following on LiveJournal, which is so funny because it wasn't my name but then somebody like at school figured out was me and I was like so scared but the reason that I was scared is because it was all like fan fiction between like Edward Cohen and Jacob like making out and I was like yes you were obsessed with Twilight oh I just know I like literally was like I remember and I talked about this I'm still so close to my high school friends but it was I wouldn't say traumatic but it was like pretty rough for me and I was like oh my god it's gonna be horrible and then I was like what's the worst Yeah.

16:30So did you fangirl when you put the Taylors on the cover of this month's Cosmopolitan, Taylor and his wife, Taylor Lautner?

16:36Willa Bennett: I honestly didn't. Okay. The time has passed. Team Edward. Yeah. Duh. No. Okay. Here's what I'll say. Hello. Here's what I'll say. And this is what I said to his face. Taylor Lautner, very sweet about this. I was like, you know, what's cool. I was like, you know, what's cool about Taylor versus Edward is like, as a young person. And I think a lot of, a lot of young people feel this way about Summary Turn Pretty. But when you're watching Edward and Jacob, you actually fall in love with parts of both of them. You're like, I love the like moody boy. That's Edward. But then you also like you do want to date your best friend.

17:09Willa Bennett: And that's Jacob. And I feel like there was a lot that Jenny took in the Summary Turn Pretty where it was like Jeremiah and Conrad is the exact same exact same model. Yes. And so, yeah, I think we can all relate to that. There's parts of people that I think we pick up on and we wrote a lot about that. And I think what was cool about the Taylor's piece is I kept being like to the writer, I was like, it is connected to some right term pretty. And there's such a model of like, we look for these types of two tropes. And it's kind of like Mary Kay and Ashley when we were growing up. It's like, you're both Mary Kay and Ashley, and that's why it works.

17:39Willa Bennett: So I don't know. It's very interesting to think about. While we're talking all things fashion, a quick pause because we need to talk about spring and what's on my radar right now. As the weather is really starting to shift, I always feel that instinct to lighten everything up. The fabrics I'm wearing, how I'm layering things, and even how structured I'm dressing. And this season, I have been so drawn to linen. It's my favorite spring fabric. And I have actually found some of my new favorite pieces at Banana Republic that I feel are exactly aligned with how I want to get dressed right now. I have said it before, but Banana Republic does linen the best.

18:14They are so good at it. And at this time of year, it becomes such a staple for me because it's breathable, polished, and incredibly versatile for anything I need to get dressed for. One piece I'm really loving right now that I can't wait to style is their linen oversized shirt. It's the perfect layering piece and also great for transitional dressing between winter and spring. It's that slightly relaxed button down that you can wear, maybe open over a tank top, you can tuck it into trousers, or even just a light layer over a dress. I'm also really into the linen pull-on pants. Pull-on pants might seem a little bit casual, but let me tell you, these are my favorite pants in my closet.

18:51They look so nice and structured, but feel so soft and feel like the kind of pant that you can just wear relaxed with a sandal, but then also dress up at night. For travel especially, if you are someone who has a big trip coming up, I cannot recommend these pants enough. They're so perfect for by the beach, but also are that pant that you can wear traveling. These are the dream travel day pant. Again, they look put together but feel so comfortable. And then lastly, let's talk about my dream piece for spring dressing. It's the linen maxi dress. This is about to be my hero dressing piece for spring.

19:25I can't wait to wear this literally everywhere. I want to wear it with flats and like a sweater over my shoulders for a daytime event. But then with a heel and maybe like a beautiful necklace or an earring for dinner at night. It's also the dream vacation piece. Like I want to wear this on the beach somewhere and just feel so relaxed and so beautiful and so effortless. I think what's best about this piece is that it's one of those pieces that transforms. It's perfect for anything you have. And that's always what I'm looking for. I think during transitional seasons, right? It's pieces that can go anywhere with me and look really good.

19:56But beyond linen, I really rely on so many of their other fabrics, like heritage suede pieces, like this amazing blazer that I'm wearing right now. I've paired it with my high rise 90s jeans in a dark wash. And I love these two pieces together. They're the kind of pieces that have just earned that permanent place in my wardrobe.

20:11Willa Bennett: amazing staples for every day. We're about to head into event season as well. So spring weddings, dinners, trips, and I'm thinking a lot about packable pieces that don't lose shape and ones that can move from day to night without overthinking it. I love packing linen pieces for that reason because I can easily take them from like daytime by the pool to nighttime and not overpack. That's really what my spring wardrobe is all about right now. I'm thinking ease, versatility, flexibility, and pieces that go with me everywhere. So if you are thinking about refreshing your closet right now, maybe you're packing for a spring trip, you can shop new arrivals right now at Banana Republic.

20:47On this note, I would love to hear a little bit about how you decide what and who to cover. I mean, the tailors were so specific. Like to a certain person, they'd be like, oh, the guy from like 15 years ago. But to someone who like us is chronically online, you know that that cover is super warranted. So how much of what you cover is based on instinct versus analytics?

21:08Willa Bennett: Honestly, it's both. I have a really, really really great team and a lot of the like that I that specific idea came from a Wednesday office hours so like all the time people are pitching ideas I love a good pitch I'm big email girl like uh I love like a really strong email pitch people on my staff all different levels know they can just like email me at any time with a pitch and like that was one that came out of an office hour and then someone followed up via email and we pursued it and we figured out that too. Lautner had a ton coming out. We figured out the podcast. We timed it with the schedule.

21:41Willa Bennett: So a lot of it's like timing, relevancy. What do they have in the works? And then other times, there's a good story. It was like a Valentine's Day story about a couple that like he met a fan, Taylor, and they have started this beautiful life together and they've had to navigate so many things. And now she's entering the spotlight and he's coming back into the spotlight. So there were layers to it where I think just journalistically, it's interesting. But yeah, I come from social like you. So I am very analytics focused. I think, you know, we're kind of getting out of this like traffic era into more real engagement.

22:15Willa Bennett: And I feel like we've been there for the past like year and a half ish, two years, three years. But I really think in the coming year, we're going to see more and more like old school editorials and people really investing in like that type of storytelling. So I'm excited about that personally as an editor. I feel like I get to be a real editor and less of like audience engagement in the coming years, hopefully. But yeah, I look at analytics obsessively and I think time spent is like my favorite metric, especially on articles, because I'm like, I think it's that you read, a person reads so many articles in a day.

22:49Willa Bennett: It's like to stay on one, though, that's the test. Like how many articles have you like read all the way to the bottom and then maybe scroll back up and then all the way, you know, it's like to me that is like we're doing something right. And that's the metric I'm most obsessed with right now. But it changes. Is there a story that's been like a home run for you? Oh, that's a good question. I've been writing a lot about AI and dating and I've really been noticing like our audience really curious about it and really reading a lot. So that's like something I'm personally interested in because I am yet to be in a romantic relationship or dynamic where somebody's like my ex is an AI bot and I'm trying to imagine what that would be like and I would hope that I would be accepting and curious, but that's something that I'm seeing a lot of our audience fascinated by.

23:37Willa Bennett: So they're reading a ton about it. What do you think of that? I'm trying to find my way in here. I need a little clarity, I feel. So when your audience is coming to you asking about AI and dating, are they asking because they're like, oh, I can tell this person's dating profile is written by AI or they're quite literally dating the voice version of their AI? All of the above. Like there was a trend that we were covering pretty all encompassing about like men putting dogs in their profiles on dating apps because they get more matches. Slam dunk. Oh, really? I mean, if you're a dog person. I feel like I wouldn't care, but whatever.

24:19Willa Bennett: But then they'd have to tell the girl a couple of dates in like, hey, it's not mine. Okay. Then that's an immediate. You left the most important hook of the story out. that's called fraud. Well, that was that was a big question. We were like, is this catfishing? Is it not? Absolutely. But we try to lead with curiosity. It's personality catfishing. OK, that's a take. So we did a lot of stories on that right now. We're in this we're in this era of being like people are now starting to date and finding out that like, oh, my ex was an AI bot or so like their person they're currently seeing casually or more seriously, eventually was in a relationship with an AI bot.

24:57Willa Bennett: And like, how do you talk about that? Do you talk about it as a real relationship? Do you not? So that's been really interesting. So we've been covering like AI dating. So what angle did you take? We always lead with curiosity and we ask questions and we're not like good or bad. We're just like, this is happening. And our culture writer just did a brilliant piece where it's basically like the AI bot can't have feelings, but your partner actually can have feelings. Right. So like, let's talk about how we can support your partner and like figure out why your partner had those feelings and what this thing represented without maybe judging them and like starting there.

25:30Willa Bennett: But it's going to unfold in real time. We don't know where this is all going. I'm excited to see that story unfold. And I also really like that your POV on most things is that you lead with curiosity. I think that's really cool. You got to. Like you can't be telling young people that like the way that they're dating is bad or good. It's like more nuanced than that. And I feel similarly with personal style. I feel like you talk a lot about personal style on this pod. And like, I think it was Brenda Hashtag was like, she went on this rant about being anti-personal style. Iconic. That is, that audio lives in my brain daily.

26:05I go to sleep in it and she knows it. It was one of the most iconic moments on this podcast ever.

26:09Willa Bennett: Yeah. She basically, guys, if you haven't listened to this episode, you got to, but she basically was like, personal style is not just about what you wear. It's how you treat the waiters. It's how you talk to your mom. It's how you hang out with your best friends. So good. It is, has everything to do with every aspect of your life and not just physically what you wear. And I was like, yes. And I very much champion that at Cosmo where I tell my team, I'm like, it's not about just how you dress. It's also like who you love, what you love, what brands you support, what brands like you gift to people.

26:33Willa Bennett: It's all of it. So I've really, I loved that snippet and I love the work she does. And I completely agree. Okay. Quick pause from today's episode, because I have to tell you guys about a few of my favorite pieces that have been on my mind this spring from one of my favorite brands, Banana Republic. Lately, I have been so intentional about what I'm adding to my wardrobe. I'm really in this phase where I care a lot more about quality, pieces that just feel worth investing in that I will actually reach for over and over again. And Banana Republic has always been my tried and true. They have always been known for their workwear, especially those iconic 90s and early 2000s campaigns, which I feel like is really trending right now.

27:11For me, getting dressed for work doesn't really look the same every day. Some days it's a 9 a.m. meeting, and other days it's recordings, fittings, events. So I really need pieces that just feel put together and super easy. The archive-inspired suede jackets, like this one, feel very classic Banana Republic. It's structured, but still really relaxed. And of course, the tailoring has such a great polished look, but it's genuinely comfortable for your everyday life. It's that balance of structure and ease that I'm always looking for in my wardrobe. So for all of your spring shopping needs, shop New Arrivals at Banana Republic.

27:44Willa Bennett: While we're talking about talent and the show, I want to get into how you think about talent in general, because it's really fun to see you specifically in who you choose for covers and features and editorials. I think about covers of Vogue, ones that have like fallen completely flat with like mega stars, right? But I feel like I'll see your covers sometimes on my feed way more than that. Like Macaulay Culkin and Brenda Song's cover was literally everywhere. I saw it everywhere. And it's interesting to me how that star power dynamic has really shifted. How do you think about it and how does it impact your choice on who you're featuring?

28:20Willa Bennett: I think it's the same with ideas on the editorial side. Like it really, to me, is about the story. I think Macaulay Culka and Brenda's song, which was my first cover as editor at Cosmo, was really about their love and like putting a relationship on the cover because I felt like, to me, Cosmo was this like historic, amazing, iconic brand that really stood for love and relationships. And I felt like it had maybe kind of like shied away from that with different priorities and traffic and social. And, you know, at the end of the day, it's like, wait, what is Cosmo? And to me, it was so clear that should be about love and relationships.

28:56Willa Bennett: And so we really wanted to put a relationship in that way on the cover. And I mean, they're just the most amazing couple. I really, really, really like loved working with them. Macaulay on set, I'll never forget this. I was like, so why did you say yes to this. Like all respect to myself. And he was like, he looked at me and he said, I'm doing this for my kids so that they'll have this magazine forever. He's like, I want them to know that like mom and dad really love each other. And like, that is like everything to me. Because like they actually speak about press, like they neither are promoting anything.

29:33Willa Bennett: They really did it because they were like, I think they were just like Cosmo's amazing. And like, you know, they spoke to we had a couple calls and they were sold in on my vision and but yeah they're so special and every time I see them Brenda Song by the way is like so amazing and so articulate and so smart and I assigned the story to Hunter Harris and she went to dinner with them and I remember she texted me right after being like Willa they're really in love like they're the real deal oh and they have such an interesting story like they really do I would encourage you all to read it so I don't I don't want to give away the ending but like their love story is really really really special.

30:07Willa Bennett: And so I think similarly after that, I did Dochi on the cover. And after that, we did Margaret Qualley. So I feel like for me, it's like really about the story. Margaret's mom had been on the cover. It was our anniversary issue. I had a very specific vision. Dochi, I wanted to really honor this legacy that Cosmos had of like really, really looking at emerging talent. And when we booked her, it was before Tiny Desk. So it was like way before. And then I remember I'm sitting at the Grammys and she won and gave that incredible speech in Tom Brown. And I was like, holy shit, she is it. So yeah, it's like timing, it's instincts.

30:44Willa Bennett: But for me, I'm really always looking at the real story. Over star power. Yeah. Yeah, I don't think it lands like it used to, in my opinion. Yeah, I just think it's different. And like, I think there's also people who like, are such incredible actors or musicians or artists. And like, maybe they don't go viral, but sometimes I'm like, who cares? Around every cover, there's always conversations of like, there's the biggest person you could get, who's promoting this, who's this. They're doing this many covers. You could also go the route of like somebody that maybe no one knows, which is like very powerful in its own way.

31:19Willa Bennett: But I'm always like, what's the story? Like, what are we going to write about? What are we going to see them in? What clothes do we want them to? Like, it's really about all of it, all the details around it. And I think more and more like the internet can tell. they can really just see what is the intention behind it and my vision just needs to be so clear so like if a talent does want to do Cosmo they know what they're getting and that's always my goal. Sydney Sweeney is on your most recent cover someone who I feel has a lot of controversy she's very polarizing right now and Cosmo to me has always been especially your Cosmo has been a platform that covers everything politics women's issues love dating all these things it's a very outspoken platform.

32:00So I would love to hear from you a little bit about that choice and how that landed.

32:05Willa Bennett: Yeah. So Sydney Sweeney has Euphoria season three. She had two movies she was promoting. There's some Oscar buzz around her. And we actually booked it, I think, a couple months before July when her controversy blew up. And, you know, there were a lot of conversations like, OK, the discourse around her by the time we booked it from the time we shot it to even the the time we printed it was like changing so quickly every single day. New controversy, new discussion, new conversation. And again, like the context just completely continued to change. And I spoke for a long time with the writer up until like literally the final five seconds of shipping it up until like even shipping it to the digital iteration.

32:47Willa Bennett: And I think where I netted out was really like empowering her to write about the moment. I was like, this is a moment. And this is actually like quite Cosmo to cover this of like what is happening like how has this woman become this lightning rod so quickly so drastically and how has her body become such like a mirror for so many things going on in the world right now and really like kind of become this like documentation of the internet and so that's what she did she wrote a great piece it was a hard piece I think it's really hard to look a celebrity in the eyes and ask really hard questions over and over and over again and not necessarily get an answer and keep going.

33:30And I think that's something you learn

33:32Willa Bennett: in journalism school. But I think she really did it. She really challenged her. And so the piece kind of honored that part of Cosmo's legacy where we would document. We had Pamela Anderson in the in the height of Baywatch. We, you know, we've had these moments where they are more contentious and fast changing and we did our best to cover the moment. But it really was more about the moment than maybe just her celebrity on the cover. And that kind of goes back to what we were talking about with, it's just the story. I'm curious what the process was of editing that. Was there anything in that that felt, I know you told me that you worked really closely to it.

34:13Willa Bennett: yeah I feel like for me I really do think about every detail and I don't know if that is coming from social or you know coming from my digital background but like I really think every detail matters and I feel like me the writer a creative director a visuals director talent director really were going back and forth about all the different details of like how we were going to push her, how she was going to look, how she wasn't going to look, where we were going to hear her out, where we weren't. And it was just very intentional. It was very contentious. And I think the phase we're in right now with celebrity, like, I think it's really easy to just cave to celebrities.

34:56Willa Bennett: We were in it to capture the moment and really be like, this is the moment we're in. And even watching the discourse that happened when it was released, it really is a reflection of like where we are right now. and I think a lot of the comments were like talking about how like this is the moment we're in and like what does this mean and I think it wouldn't be wise for Cosmo to be one note all the time anyway and so like we do need to surprise and challenge and really like sit with the fact that like she she is a really incredibly influential celebrity to our audience. Euphoria is huge her two movies were huge at least one of them was very huge the other one christy were we're still waiting on results but you know like we need to talk about like what influences and i and i thought alexandra the writer did a did a really excellent job taking this like contentious booking that again like was changing rapidly in front of all of our eyes and really reflect back what does this mean and i think a lot of magazine covers i mean i think back to you know i have megan fox on the cover of GQ in my living room.

36:04Willa Bennett: I have, you know, Timmy Vogue, which I know we've talked about, The Space in the Back. Like I have some and Frank Ocean for GQ, which was Will's first. Like I really do think a lot about like magazine covers that stop time and like make me think about the moment we're in. And I would hope that if nothing else, people at least engaged with it. Like you don't necessarily have to agree with every single cover, but like I just hope that we can continue to engage with content that often makes us uncomfortable or just ask questions of ourselves. Does it frustrate you when people see that cover and automatically go in for like maybe a negative comment before they read the story?

36:44Because it was funny, even when we were chatting, you were like, read my editor's note, read the story. Yeah. What do you want that to signal to a reader? Is that is it an examination? Is it an endorsement? Where does that lie for you?

36:54Willa Bennett: I think for me, I really do like make an effort to let people in, like whether that be emailing people back all the time or like taking informationals. Like I'm very like, tell me what you think, tell me what you think. So I was not at all like read the piece, stop commenting on Instagram. I'm not really like that. I'm like, I feel very grateful that we have cultivated an audience at Cosmo that like will tell us like what they do and don't like. So that part doesn't really bother me. But I do think a cover isn't necessarily an endorsement. And I think that is something that has changed in media.

37:30Willa Bennett: And I think that's something we continue to see. And I think a cover for me, at least, is like a moment in time and what it captures. And I think all magazine covers or even magazine like journalism that, again, like I go back to that feeling of like seeing something and it stops time because you're so curious about it. That's never necessarily an endorsement. It's never been that way. And I think, you know, as the internet has progressed and the platforms have progressed, obviously things will continue to change. I think that's maybe one thing that is interesting about this moment. It's like people just see a cover and then they scroll through and like have an opinion.

38:04Instead of seeing the whole thing.

38:06Willa Bennett: Yeah. It's like read the piece. And I also think I come from a school of journalism where we always put tricky people on the cover and we always explore controversy. And, you know I think the worst thing we could be in this divisive time is just like echo chambers on either side it's like let's engage with each other and really cover it and I really like the pieces I've seen in journalism recently that have done that and I try to engage with them because I'm like this can't be easy but we are in unprecedented divisive times and I think the worst thing we can do is just stay in our corners and not engage with each other.

38:41There's a really big conversation right now about editorial rage bait. And I'm curious to hear your thoughts on that. Obviously, I think that there's one pool of, you know, we're talking about controversial stories, examining them, good journalism. That's one thing. But do you think that this conversation about rage bait in the editorial world is real? Like, do you think that that actually could be something that is being factored into the back end?

39:04Willa Bennett: No, I don't know. I have gotten asked that question, I think, just given my background. and I don't know. I don't think so. Like, I don't know. Maybe I'm like so online that like, it does not fool me. I see something in RageBate and I'm like onto the next. Like that's not time spent. But so you do think that there are certain things out there that exist as that? Not from publications. Okay. I think that like our resources are so strapped and we have to prioritize so much. It's like, I would be really surprised if there was any editor that was like out here doing stuff for clicks right now. Like, right.

39:37Willa Bennett: We have to prioritize like to the 10th degree, which I actually think sometimes can be good for creativity. And so I think if anything, it's like no one's doing stuff for Rage Bait. A lot of people, not myself, thought that the Timothee Chalamet vote cover was Rage Bait. Yeah, I didn't at all. I told you this when we were catching up, but like I love that cover. Say more. In my living room. It's just different. What did you love about it? it's in my living room. I just love when an editorial like becomes like an item like that. I don't know. Like it is in my living room. It's like out on display.

40:11Willa Bennett: But I also like love magazines truly. And I love like the collect. I think it's like a moment in time and then you like have it. I don't know. So I don't know. People were really critical about that. And I was not agreeing. You know, it's interesting. I've actually really liked that you've said this idea that magazine covers are a snapshot in time. I don't know what they used to create that cover, but a lot of people thought it was like a great snapshot of where we were at in like an editorial creative landscape right now with like AI and like new imagery and things like that. And so to me, those two things kind of add up.

40:46Willa Bennett: Did you see the like A24 video that went viral with Timmy where he's like the Marty Supreme one on the Zoom? Well, there was like the Zoom with the A24 team and he was like, Christmas Day, Mercury Supreme. Okay, so once you watch that, don't you understand the Vogue cover? Yes, but they didn't come out at the same time. Yeah, of course. If they came out at the same time, I'd be like, I get it, bye. To me, I was like, Timmy has made this into a promotional moment for his project, which is kind of genius. To me, it's like, he told his story. Right. And I would have loved to be in the room between him and Annie Leibowitz.

41:19Willa Bennett: Editorial's in an interesting place. I'm excited about it. I think, I just, I don't know. I feel like this real moment in time where I'm like editorial does matter and it really can change people and it can change legislation and law and like the way people think about the world. And I think we're going to see that more and more. And I think to run a brand like Cosmo and that has such a rich legacy is like such a privilege. And it's like the only thing like keeping me going these days. I think we live in very divisive times, but to have a publication that's like mass and bringing people together is the answer.

41:54Willa Bennett: And again, I mean, it comes down to leading with curiosity. I feel like I'm so tired of magazines telling me what to wear and think. I guess I've just like always been dressing the way I want. And so I like that mold has never worked on me. So I think that we're in this moment that's exciting where it's like people are people are coming to us because there's so much out there and we have a platform that you can trust. And so I'm excited. And thank you for reading. So honored that you read the Sydney piece and my ed letter. And you're so sweet. You texted me about it. It really does like mean the world.

42:25Actually, what you just said really resonated with me where you were like, I'm so sick and tired of having magazines tell me what to be and how to wear and how to dress all these things. I don't think it's dawned on me that like that really is the shift. Like growing up, I think we were so defined by magazines. We were so defined by like Teen Vogue was a Bible. I had you know like Cosmo was a bible 17 was a bible these magazines that like shaped us and kind of made us who we are and I think we have iterations of that today but to kind of flip that on its head is a really cool angle yeah even men's magazines growing up like I love them more than

43:01Willa Bennett: life itself but it would always be like this is how you do this this is how you do this is how you wear a tie it was always like how to and I was like wait yeah I don't like t-shirts over dress shirts and ties but it was like that's what GQ or Esquire said was cool at the time And then later I was like, wait, that is my taste. Like my taste is that I don't like that. So I don't know. Like I think that developmentally is so important to rectify. And I tell readers all the time who want to come into magazines, I'm like, just notice like your taste and like really cultivate that. That is so important.

43:30Willa Bennett: And to go back to Brenda's amazing viral quote, like it is it's all connected and it's how you treat someone and how you look at the world and your taste is everything. And I think increasingly, as we see AI, taste is going to become more and more important. I want to look forward a little bit. Yeah. Obviously, you are working on content daily that has focused on Gen Z. I feel like in the last five years, everything is Gen Z. We're marketing to Gen Z. We're, you know, like that is the goal consumer. For you, are you thinking about what's next after that? Is that still the goal? Like, how do you bridge that gap?

44:07And also if you are marketing towards the next generation, like what does that look like? I'm sure people are really curious to hear about like what is after the big wave of Gen Z.

44:16Willa Bennett: I feel like we're still in the Gen Z era as a culture. I mean, even watching the Olympics, like I keep saying to my team, like this is the Gen Z Olympics, the EDM, the haircuts, like the outfits, the outfits. Yes, totally. So that is that answer for Cosmo. I mean, I'm going with the readers. Like, to be honest, we have a lot of really young readers on TikTok who are discovering us through TikTok and then coming to subscribe to the magazine and then coming to our events. We definitely have a Gen Alpha audience on some of our social platforms. But then on site, we have, you know, we have people who have been subscribing and coming to our website for like 40, 50 years.

44:54Willa Bennett: And that's exciting to me, too. So I'm really like, I'm with the audience. I want us to be there because we all come together because, you know, know, we care about pop culture, love, personal style, all the things that bring us together. But I will say from like an advertiser perspective or just like being out in the world, I feel like everyone's pretty focused on Gen Z still. Yeah, for sure. I don't think it's faded. And I think Gen Alpha is like a tiny bit too young. But I think we'll start to see that in the next couple of years. When does Gen Alpha start? I think it's 2010. So interesting.

45:24Willa Bennett: So born in 2010-ish. So we'll sort of see it more and more. But I feel like even just like what I see from like TV, movies, like all the marketing, I feel like is still pretty Gen Z focused. I'm sure a lot of your readers want to know this from you. But I also want to know this from you. In just kind of the new age of journalism and media that you're building, what do you think the next generation of journalists and editors need to focus on from a skill perspective? Like what does that next era look like? taste, perspective, really cultivating your voice. I think voice is everything. I mean, again, even just like being able to like look at a photo and really articulate what you're seeing, I think is so important.

46:06Willa Bennett: And again, like will become increasingly everything. Taste though, I think taste is like the most important skill that someone can have as an editor. How do you cultivate your taste? It's a really good question. I mean, I should ask you, like, where did you get your taste? I can pinpoint like certain people, certain jobs that have like come in and out certain things about my upbringing that have influenced it. But curiosity, honestly, like I really think like I was always obsessed with magazines growing up and that was just because I was like genuinely curious about fashion. But yeah, books, movies.

46:39Willa Bennett: I had a very literary family. So like I give that a lot of credit. I was always reading so many books and anytime something happened to me, I would like go and seek out the answer. And also the internet. I think the internet changes your like continues to shift your taste so drastically. And I think even like the internet circles we were in in middle school, like that really changed how I wrote, like for sure. So I think it's a combination of all of it. I do worry a bit about TikTok sometimes about taste because I feel like the trends are just like so quick. And even with my younger siblings, I'm like, wait, why do you like that?

47:12Willa Bennett: Wait, why are you wearing that? So I think the pace at which what I'm noticing will continue to get quicker and quicker and quicker, which isn't good or bad. It just is different. But I really would say to a young editor or someone trying to figure out their voice is just like stay true to like yourself and comment on trends, but don't jump into all of them. This was so fun. And what a weird full circle. Amazing thing for both of us. Anytime you brought up middle school, I was like, wow, I could visually close my eyes and go back to that. And I have to find a fun picture of us. I will. Oh, this comes out.

47:47You still have the archive that far back? I don't.

47:50Willa Bennett: Probably. I could find something. I hope you do. Well, thank you for having me. And yeah, it's so, so good to see you always.