How Anna Wintour's Vogue front covers made a statement to the end

Anna Wintour's 37-year tenure as editor-in-chief of American Vogue has left a lasting legacy - over 400 covers that have sparked controversy and conversation. The latest issue, featuring Timothée Chalamet on its cover, has already ruffled some feathers online.

The image, shot by Annie Leibovitz and styled with a Celine white polo neck, long cream coat, and embroidered jeans, has been met with criticism from some quarters. Comments on Vogue's Instagram have included "I'm just horrified" and "when you ask ChatGPT to do your cover", with some users expressing disappointment that the magazine seems to be playing it safe.

However, others are taking a more nuanced view. Magazine store founder Jeremy Leslie notes that Chalamet is part of a long line of Vogue covers that have pushed boundaries and explored themes of identity and aspiration. From Madonna in 1989 to Kanye West and Kim Kardashian in 2014, Wintour's magazine has never shied away from controversy.

Leslie argues that this latest cover is a statement - one that signals the end of an era for Wintour as editor-in-chief, but also sets the tone for what Chloe Malle will bring to Vogue in her new role. As head of editorial content, Malle faces the challenge of defining wealth and aspiration in a rapidly changing world.

For some, this will mean embracing a new era of "nepo babies" and social media-famous personalities. But for others, it may also mean moving away from the likes of Wintour-style talking point covers that have become a hallmark of the magazine's past.

With Vogue World set to take center stage in 2026, with its focus on craftsmanship and creativity, some wonder if Malle will be able to strike a similar balance between controversy and relevance. One thing is certain - Anna Wintour has left an indelible mark on American fashion, and her legacy will continue to shape the magazine for years to come.
 
I think it's cool that Vogue is still pushing boundaries after 37 years under Anna's leadership 🤯. I mean, yeah some people might not love the latest cover, but who doesn't love Timothée Chalamet? 😎 But seriously, I think it's awesome that they're giving Chloe Malle a chance to put her own spin on things. We all know that fashion is about taking risks and trying new stuff 💁‍♀️. The fact that they're focusing on craftsmanship and creativity for Vogue World sounds like a great move - it'll be interesting to see how that plays out 🤔. And let's be real, Anna Wintour's legacy is one of the most iconic in fashion history 💯. She might not have been everyone's cup of tea, but she definitely made her mark on the industry 🔥.
 
🌞 I think this cover is actually kinda cool! Timothée Chalamet is so talented and it's awesome that he's being featured on Vogue's cover. Yeah, maybe some people are a bit shocked at first, but that's what makes it interesting, right? It's like the magazine is shaking things up before Chloe Malle takes over 🔄. I love how Jeremy Leslie pointed out all those iconic covers that pushed boundaries and sparked conversations - that's what Vogue has always been about! 😊
 
i think its kinda cool how anna wintour pushed boundaries with those old covers lol like who would've thought madonna on the cover back in 89? but at the same time, i get why some ppl are sayin this new cover is playin it safe... timothée chalamet is def a talented actor and all, but is he really pushin the fashion envelope or just another 'nepo baby'? 🤔👗 also gotta ask, whats up with all these designers on vogue's covers lately? like, i love celine as much as the next person, but are we seein a little too much of the same old thing in terms of style? 🤑
 
I'm low-key disappointed that Vogue isn't pushing harder for some real edge with this new cover. I mean, Timothée Chalamet's cool and all, but we've seen so many iconic covers from Madonna to Lady Gaga over the years. And don't even get me started on the Celine outfit - it looks like something Alexa Chung would wear 🤣. I think Chloe Malle has her work cut out for her if she wants Vogue to stay relevant. We need more bold statements, not just safe, Instagram-friendly choices 💁‍♀️. Still, I'm excited to see how she's gonna shake things up and bring some fresh energy to the magazine 😎
 
idk why ppl are so salty about timothée chalamet on the cover tho 🤷‍♀️ he's a talented actor who deserves some love 💁‍♀️ & let's be real, annie leibovitz is a genius photographer 🔥 she always brings something special to her work. wintour's legacy is all about pushing boundaries & sparking conversations 💬 & that's exactly what this cover is doing 🤔 plus, who says vogue can't have some comfy celeb covers every now & then 😂 it's not like they're getting rid of the edgy stuff or anything 😉
 
I gotta say, 400 covers with controversy sparks convo is a big deal! 🤔 But I think the debate around this latest issue is valid - is it playing it safe or just sticking to what works? I love how Jeremy Leslie points out that Vogue has always pushed boundaries, but now they're trying to adapt to a changing world. It's gonna be interesting to see how Chloe Malle defines "wealth and aspiration" in 2026 🤞. And with Vogue World taking center stage, it'll be cool to see what kind of new wave of fashion we get! 👗
 
I'm so over this obsession with "nepo babies" 🙄... just because Timothée Chalamet is famous doesn't mean Vogue needs to give him a cover every 5 mins... I mean, where's the depth? Where's the conversation starter? This latest issue feels like just more of the same - safe and boring 😴. And what's with all these armchair critics on Instagram? Can't they come up with something better than "I'm horrified" or "when you ask ChatGPT to do your cover"? 🤷‍♂️ Get a life, people! 💁‍♀️
 
🤔 I mean, what's the big deal? The kid looks good, he's famous, and Annie Leibovitz shot him 📸. It's not like they're selling out or anything, it's just a cover shoot 🎉. And honestly, I'm kinda tired of people calling out Vogue for playing it safe all the time 🙄. Anna Wintour has been doing this job for 37 years, she knows what works 💁‍♀️. The only thing that's changing is the editor-in-chief, so we should be chillin' about the whole "new era" vibes 🤷‍♂️. Let Chloe Malle figure it out, I'm good 🙃
 
🤔 I gotta say, 400 covers in 37 yrs is crazy! 🙌 Not all of 'em were gonna be love at first sight tho... some people just got played 😂. But honestly, the mag's always been about pushin' boundaries & sparkin' conversations 💬. Like, remember that Madonna cover back in '89? Game-changer! 👑 And Kanye & Kim? Total disruptors 🚨.

Now, I'm intrigued by Chloe Malle comin' in & definin' what wealth & aspiration mean in 2026... is she gonna keep it real or play it safe like some others? 🤔 Only time'll tell! One thing's for sure tho: Anna Wintour left her mark & it's still feelin' 💯. Bring on Vogue World & let's see where this new era takes us! 🌎
 
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