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After a seemingly successful and inescapable red-carpet promotional tour, the reviews of Ryan Murphy\u2019s Hulu show <\/strong>All\u2019s Fair<\/strong> have been impressively scathing.<\/strong> The Wrap\u2019s Kayleigh Donaldson <\/span>wrote<\/a>, \u201cIt\u2019s truly baffling how terrible \u2018All\u2019s Fair\u2019 is.\u201d Sophie Gilbert <\/span>wrote in The Atlantic<\/a>, \u201cThe writing suggests that ChatGPT was asked to emulate <\/span>Fifty Shades\u2019<\/span> E. L. James, and however cringeworthy and brand-name-peppered that sounds, I can promise you it\u2019s so much worse.\u201d (I watched all three available episodes and I\u2019ll be back in your inbox Thursday with a fashion review.)<\/span><\/p>\n<\/li>\n
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Well, this has to be the work of Kris Jenner: Just about every major outlet has run with the story that <\/strong>All\u2019s Fair<\/strong> is actually a triumph despite how bad it is because it got the most viewers of <\/span>any Hulu debut in three years<\/a>, with \u201c3.2M globally after three days of streaming.\u201d I can think of creators whose TikToks regularly get more views, but for what it\u2019s worth: <\/span>The Bear\u2019s third season <\/span>got 5.4 million<\/a> in its first four days of streaming.<\/span><\/p>\n<\/li>\n
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Speaking of Kris Jenner, her <\/span>007-themed 70th birthday party<\/a> was basically James Bond sponcon<\/span><\/strong> thrown by Jeff Bezos and Lauren S\u00e1nchez in their $165 million Beverly Hills mansion. Everyone from Beyonc\u00e9 to Prince Harry and <\/span>Meghan Markle<\/a> were there. (Amazon acquired the rights to the James Bond franchise earlier this year.)<\/span><\/p>\n
![](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!U8c1!,w_640,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F__ss-rehost__IG-meta-DQ5FTEMEklg.jpg\"\/)
<\/a><\/p>\n\nKris Jenner on Instagram: “0070 \ud83c\udfb0\ud83c\udfb2\ud83d\udda4\u2665\ufe0f\ud83c\udf78”<\/p>\n<\/div>\n<\/div>\n<\/li>\n
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This <\/span>story in the <\/a><\/strong>New York Times<\/a><\/strong> about Americans buying more super yachts<\/strong> because Trump made them so rich, wedged into a feed along with news about the administration continuing trying to block food stamps for low-income people, felt nightmarishly dystopian.<\/span><\/p>\n<\/li>\n
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I\u2019ve been thinking about Michelle Obama\u2019s favorite mall brands<\/strong> as she promotes her new book <\/span>The Look<\/a>. One of them was Ann Taylor, which has a great <\/span>lace-trimmed tank on sale for $40<\/a> and <\/span>a cashmere crewneck on sale for $96<\/a>.<\/span><\/p>\n<\/li>\n
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My friend <\/span>, author of Wearable Art here on Substack, <\/span>opines on the question of<\/a> \u201cwhy fashion is so hideous right now,\u201d<\/span><\/strong> writing, \u201cDo [people] want their outfits to reflect the existential dread and chaos around them? Or do they want clothes that will allow them to move through this world with a little dignity and grace?\u201d<\/span><\/p>\n<\/li>\n<\/ul>\n
Well, I was wrong.<\/p>\n
I thought Anna Wintour would make a splash for her last <\/span>Vogue cover and book, like, Kate Middleton or, I don\u2019t know, Oprah. Taylor Swift\u2019s wedding dress reveal? Someone or something\u2026 mega.<\/span><\/p>\n
I did not expect a solo man, Timoth\u00e9e Chalamet, floating around in outer space like a paper cut-out superimposed onto a 1,000-piece puzzle or an old mousepad.<\/p>\n
<\/p>\n![\"COVER](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!Unen!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa0c139b3-7c64-4e38-a644-d61bc499b94b_2560x3094.jpeg\" "\\"COVER")
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But that\u2019s Anna. She probably didn\u2019t want to make a big deal over her last-ever cover as editor-in-chief before the task passed to her new head of editorial content, Chloe Malle, because that\u2019s not her style. She\u2019s the type of person who would rather <\/span>throw a birthday party for Baz Luhrmann<\/a> instead of for herself. She doesn\u2019t like looking back or reflecting \u2014 she always talks about moving forward. To wit, the confirmation we got that this was, in fact, her last cover was buried as an aside in an episode of the <\/span>Vogue podcast.<\/span><\/p>\n
<\/p>\n\n<\/div>\n
\nAnna Wintour’s (Semi) Exit Interview<\/h4>\n<\/div>\n<\/div>\n
<\/a><\/div>\n
The reaction to Anna\u2019s last cover has been, well, mixed at best. I saw a lot of comments about how it\u2019s \u201cgiving Canva.\u201d People did not appreciate the austerity of the inside photo spread, which Anna favorite Annie Leibovitz <\/span>photographed at a land art installation<\/a> in Nevada by artist Michael Heizer. Still others wondered why she decided to put a white man solo on her final cover. (<\/span>Vogue has only featured men by themselves on three covers ever: Harry Styles for December 2020; Colman Domingo, A$AP Rocky, Pharrell Williams, and Lewis Hamilton for May 20205, pegged to the Met\u2019s Black dandy exhibition and gala; and now Timmy.) <\/span><\/p>\n
Chalamet is promoting his awards-bait movie with Gwyneth Paltrow being released Christmas Day, <\/span>Marty Supreme, in which he plays a ping-pong player. (Maybe he\u2019s like a ping-pong ball in space, floating through the fashion ether, from Chanel face to <\/span>Vogue cover and back again?)<\/span><\/p>\n
Still, the cover is very Anna. It caps off a decades-long collaboration with Annie Leibovitz, mixes art and fashion (which she loves), and features an A-list star promoting a movie that seems tasteful.<\/p>\n
Anna has succeeded many times with this formula. But it\u2019s one that makes less and less sense in 2025, when so few movies \u2014 and almost none that aren\u2019t targeted to kids \u2014 open at the box office. Awards season is more and more a celebration of films few have seen by an industry prostrated before Big Tech as it carves it up like roast beef. Anna\u2019s Met Gala now even overshadows award season red carpets. <\/p>\n
This Chalamet cover is historic, albeit not for its influence. That said, Anna\u2019s tenure at <\/span>Vogue, which she edited for 37 years, has been incredibly influential. Ahead, my list of her ten most impactful covers through her years as an editor-in-chief.<\/span><\/p>\n
10 – <\/strong>HG<\/strong>, March 1988<\/strong><\/p>\n
<\/p>\n![\"\"](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!Ae9C!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffca3a034-fcff-4a88-b864-b27aba657637_914x1190.png\")
<\/div>\n<\/a>Anna\u2019s redesigned <\/span>HG.<\/span><\/div>\n
When Anna took over <\/span>House & Garden in 1987, she thought (correctly, I\u2019d argue) the photos were stuffy and lifeless. Dining tables were set with no sign of human activity and not a dinner napkin out of place. <\/span><\/p>\n
<\/p>\n![\"House](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!Yj4V!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F375d7063-f335-48cb-b0c7-b4b75f3f1197_385x500.webp\" "\\"House")
<\/div>\n<\/a>A pre-Anna House & Garden cover from 1985.<\/div>\n
She decided to introduce people to interiors photography, including celebrities and socialites. When I was reporting <\/span>Anna, one person told me it was radical for her to include a photo of a laundry room where the detergent was visible \u2014 the point is, these homes were <\/span>lived in, they didn\u2019t exist as totems to furniture. <\/span><\/p>\n
Though the interior design community was aghast at her changes at the time, including shortening the title to <\/span>HG, she established a new formula that home magazines like <\/span>Elle Decor and <\/span>Architectural Digest still use today. Those magazines are less about fantastic interiors than photographs of celebrities by their fireplaces, whether their homes are uniquely designed or just forgettable venues for high-contrast marble and kitchens with no food in them.<\/span><\/p>\n
9 – Anna\u2019s first British <\/strong>Vogue<\/strong> cover, August 1986<\/strong><\/p>\n
<\/p>\n![\"British](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!HthN!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9a960b75-9ea1-4be7-a7a5-d275b09cf0f2_1200x1632.jpeg\" "\\"British")
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Anna ran British <\/span>Vogue briefly beginning in 1986 \u2014 her first editor-in-chief role \u2014 after serving as American <\/span>Vogue\u2019s creative director<\/span> under Grace Mirabella. She took a magazine that featured fashion that was often just silly and horse-y and made it over to appeal to the modern working woman. While this upset a change-averse contingent in British media, it also setting a new standard at the title and helped to globalize her particular, no-nonsense aesthetic. <\/span><\/p>\n
8 – Anna\u2019s first <\/strong>Vogue<\/strong> cover, November 1988<\/strong><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!B_Me!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbec68f34-4c75-4d00-a2b2-678d5a0d6be9_451x600.jpeg\" "\\"Issue:")
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This cover was revolutionary for its time. Grace Mirabella had been publishing tightly-cropped headshots of models for each issue, photographed in a studio by Richard Avedon. Anna came in, canceled Avedon\u2019s contract, and decided to photograph model Michaela Bercu outside in a Christian Lacroix top and Guess jeans \u2014 mixing high and low, showcasing a casual vision of glamour that would inform her <\/span>Vogue moving forward.<\/span><\/p>\n
7 – Madonna, May 1989<\/strong><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!yFBc!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa0996f46-142a-4e22-838d-b7785f5c66c4_443x600.jpeg\" "\\"Issue:")
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This was Anna\u2019s first celebrity cover \u2014 and a radical move for the time. Madonna was highly controversial, having just released her \u201cLike a Prayer\u201d music video with religious imagery that got her Pepsi endorsement deal <\/span>canceled<\/a>. Rather than shy from the controversy, Anna rightly realized she could expand the public\u2019s idea of who belongs in <\/span>Vogue.<\/span><\/p>\n
6 – Ivana Trump, May 1990, and Melania Trump, February 2005 (Tie)<\/strong><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!CYGD!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff6494004-3a07-4f1c-a5d2-4f2ad76f6d22_449x600.jpeg\" "\\"Issue:")
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Anna put Ivana Trump on the cover around the time of her split from Donald Trump \u2014 then just a media-hungry, New York real estate guy \u2014 even though she feared she was \u201ctoo tacky,\u201d she told one of her editors at the time, as I reported in <\/span>Anna: The Biography<\/a>. As committed as Anna is to a particular taste level, she\u2019s been just as committed to occasionally breaking with it. Her instincts in this regard have often proven correct: The intrigue around Ivana was so great that the issue sold 750,000 copies, which was strong for the time.<\/span><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!dIjM!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F02b31ec6-1dbe-41ed-98d0-e53e9c2ec14c_429x600.jpeg\" "\\"Issue:")
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Melania Trump\u2019s 2005 cover, however, sold only 417,000 copies. But I\u2019m putting it on the list because, like it or not, Anna contributed to the Trump family\u2019s rise, the myth of Donald Trump as a guy who knows business well enough to get rich and land model wives dripping in couture and diamonds and Birkin bags. I wonder if, as a ardent Democrat, Anna regrets this cover today.<\/p>\n
5 – Gwyneth Paltrow, August 1996<\/strong><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!av6e!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9d720895-b867-4517-9c56-441d624ca90f_424x600.jpeg\" "\\"Issue:")
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Anna photographed Gwyneth three times before she finally gave her a <\/span>Vogue cover for August 1996, pegged to <\/span>Emma. This cover reflected the formula that Anna relied on for the next two decades \u2014 a tastefully styled A-list movie star (musicians and TV actors were rarely given top billing in these years), promoting a tasteful movie.<\/span><\/p>\n
4 – Naomi Campbell, September 1989<\/strong> <\/span><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!GeYh!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1b95e90c-ad2e-418a-abbb-8575ffa6dfcb_442x600.jpeg\" "\\"Issue:")
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Naomi was the first Black model to appear on the cover of <\/span>Vogue\u2019s September issue, the magazine\u2019s most important issue of the year. Black stars seldom covered <\/span>Vogue with regularity until very recent history, making their rare appearances all the more notable in Anna\u2019s earlier tenure. When she made the rare move of featuring a Black woman on the cover in the eighties and nineties, it only drove attention to their lack of representation in <\/span>Vogue and fashion more broadly.<\/span><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!Znx2!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9ef7ee61-4b71-43eb-96d4-0f64fdaa601f_438x600.jpeg\" "\\"Issue:")
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Around the time Ugandan model Kiara Kabukuru got the cover for July 1997, Amy Spindler <\/span>wrote<\/a> in the <\/span>New York Times about how fashion appropriated African culture on the runway and in editorials. She added: <\/span><\/p>\n
The last time Vogue had anything but a white model on the cover was in June 1993. That is, of course, not counting the May 1996 cover, which caused a stir when a fold-out cover offered Niki Taylor facing the world in suburban splendor (an itsy-witsy teeny-weeny yellow polka-dot bikini) and Ms. Campbell on the inside flap (in a leopard bikini), facing a Lancome Poeme scent strip inside. <\/p>\n
In response to that issue, <\/span>Vogue even printed a letter from a reader who wrote, \u201cFrom Naomi Campbell in an animal-skin bikini to that bizarre and unworldly layout with the Asian model a few months ago, to the distasteful, racist and colonialist depiction of a woman in Ralph Lauren\u2019s idiotic and patronizing interpretation of Masai clothing, you consistently blow it when it comes to women of color.\u201d<\/span><\/p>\n
3 – The Supers, April 1992<\/strong><\/p>\n
<\/p>\n![\"Issue:](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!fvE_!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F3001a71a-8217-45e0-8a4e-1f8e4f1b4d1b_455x600.jpeg\" "\\"Issue:")
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In honor of its 100th anniversary, <\/span>Vogue gathered ten supermodels to pose in white jeans and tied-up shirts, a recreation of an iconic Irving Penn photo. It was sort of the last gasp of this era of fashion in which models reigned \u2014 before celebrities took over covers, ad campaigns, front rows, and <\/span>Vogue generally. When I was researching <\/span>Anna, I learned that Anna actually wasn\u2019t thrilled initially about the switch from models to celebrities, despite how she helped shepherd in that era. She generally preferred the results her team got with models, for whom posing and making clothes look great came second nature.<\/span><\/p>\n
2 – Kim Kardashian and Kanye West, April 2014<\/strong><\/p>\n
<\/p>\n![\"Kim](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!kVYv!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F86436bcd-e231-4b5e-ae4a-4583e0a021e9_855x1200.jpeg\" "\\"Kim")
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Anna has talked about how controversial she knew this cover would be \u2014 how she knew people would be \u201chorrified.\u201d But she also admitted that Kim\u2019s wedding to Kanye was such an important cultural moment that she felt she couldn\u2019t ignore it.<\/p>\n
Whether it benefited her or Kardashian more, I\u2019m not sure. Some <\/span>Vogue readers to this day say the magazine hasn\u2019t been the same since, citing this cover as the moment it all went to hell. Meanwhile, Kardashian is probably one of the most famous and influential fashion \u201cicons\u201d wearing clothes today, sitting atop Skims, a more than $3 billion clothing business. Anna\u2019s approval undoubtedly helped her get taken seriously by the fashion industry and consumers, and this cover was a clear turning point in her relationship to the industry.<\/span><\/p>\n
1 – Michelle Obama: March 2009, April 2013, December 2016<\/strong><\/p>\n
<\/p>\n![\"\"](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!1DUV!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0ae52ab2-2e52-459e-9bc5-74fad5a2fed7_2315x3086.jpeg\")
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Michelle Obama appeared on the cover of <\/span>Vogue three times as first lady (Anna raised money for both of Barack Obama\u2019s presidential campaigns). These issues are now collectibles and helped cement Obama\u2019s status as the biggest political fashion influencer since Jackie Kennedy. She is to this day one of the world\u2019s most important fashion influencers \u2014 period. These covers were also a flex for Anna, showing her ability to feature one of the most important and sought-after fashion icons of her generation in three separate photo shoots. They were also a great showcase for American fashion, both Michelle and Anna being terrific champions of American design.<\/span><\/p>\n
<\/p>\n![\"Image](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!2qYp!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff00e5a09-88d7-4875-bb9e-d95e5f79a3af_1500x2037.jpeg\" "\\"Image")
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With American fashion even less dominant now than it was then (it has always struggled to compete with European houses), these issues succeeded because they captured so well specific moments in time, culture, and history. <\/p>\n
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![\"michelle-obama\"](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!aKV1!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc956b4e9-9f7a-45e2-b3cc-c3c2a833ac24_1471x2000.webp\" "\\"michelle-obama\\"")
<\/div>\n![\"The](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!3ton!,w_140,h_140,c_fill,f_auto,q_auto:good,fl_progressive:steep,g_auto\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff921c19c-4032-4889-9916-bf52f3003b58_5000x3332.jpeg\")
<\/div>\n![\"Retail](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!1rHY!,w_140,h_140,c_fill,f_auto,q_auto:good,fl_progressive:steep,g_auto\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F95a009ca-6737-4b11-ab65-6cfac16213c2_4000x2667.jpeg\")
<\/div>\n![\"Ryan](\"https:\/\/substackcdn.com\/image\/fetch\/$s_!pWgJ!,w_140,h_140,c_fill,f_auto,q_auto:good,fl_progressive:steep,g_auto\/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fac6087f0-bbe1-4432-b88c-db337538cb52_2002x1441.png\")
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