Welcome Back on the Fashion Hamster Wheel
Looking ahead at what's to come in 2026, while also looking (regressing?) back to 2016.
Hi everyone, I hope your January is everything you hoped it would be and that you’re enjoying your long weekend. I spent much of last week sending out pitch emails (to my editors reading this, expect follow-ups soon) and coming down from my blissful trip to Costa Rica, where I celebrated the 40th birthday of my friend of over 20 years. We’ve lived several lives — some of them horrific — since we met, and it’s so special that we’ve loved and grown with each other through all of them.
On my last night in Tamarindo, a few of us went surfing at sunset. I floated on my board for a while to listen to the waves and watch the sun go down, before catching what the boys called “the wave of the day.” I hadn’t felt such an overwhelming sense of hope and gratitude in a very long time, and I’m going to make a real effort to keep the spirit of that evening alive as we head into 2026.
Last Sunday, while the entire group was at dinner, I was glued to my phone, locked into the Golden Globes content coming in via X, Instagram, and Substack notes. The fashion was not particularly memorable to me this time around, but a week later, I am still a bit unsettled by how many celebrities look almost like themselves, but between extreme weight loss and barely perceptible nips and tucks, are a little uncanny valley.
I know that’s just how life is now, but it was making me feel kind of insane. I’m not proud to admit I was using the restaurant’s wi-fi to text my beauty editor friends, “[insert celebrity here] face lift? Y/N,” and forcing my mostly uninterested dining companions to weigh in as well. I turn 39 next month, and am acutely aware of how my own face has changed over the last year or two. I thought I had more time before I’d feel pressure to make more extreme, expensive changes than biannual botox to stay snatched. Guess not!
I’ve worked in fashion media for over 15 years, which I often characterize as a hamster wheel — a never-ending cycle of programming that kicks off in January with awards season, rolling straight into Pitti Uomo/Men’s Fashion Week, Couture Week, and Fashion Month, rarely relenting until the holidays arrive, affording you a few short weeks of relief. It’s surreal that it’s all starting up again, but without a full-time gig, I can dip in and out as needed to help preserve my sanity.
That said, I’ll still be following the action very closely for this letter, the pod (new ep tomorrow!), and my freelance stories, despite not being boots on the ground one hundred percent of the time. I do want to “get back out there” in a more consistent way this year, so if you’d like to invite me to your events, parties, presentations, dinners, etc., you can email alyssa.vingan@gmail.com. I am very fun! And now, some thoughts on the news:
I knew the 2016 romanticization had legs. Back in September, when supermodels, influencers, and other fancy fashion people started posting mannequin challenge videos from Parisian bistros during Fashion Month, I had a feeling the collective obsession with 2016 would grow as its tenth anniversary drew near. I was right: Last week, the internet had a field day posting memories from the simpler time, jam-packed with Yeezy/Purpose Tour/Summer Sixteen merch, the Snapchat dog filter, and full face beats. If you’d like to dive deeper into why people are so fixated on 2016 nostalgia right now, I have two TNG episodes from early December for that: the first on beauty, the second on fashion. Last week, the New York Times and Vogue Business joined the conversation with their theories on this, too. In the immortal words of Drake and Future, what a time to be alive.
Gap hired a Chief Entertainment Officer. In this newly created role announced last week, the famed mall brand tapped Pam Kaufman to build out its “entertainment, content, and licensing platform across music, television, film, sports, gaming, consumer products, and cultural collaborations — championing innovative storytelling to unlock value at the intersection of fashion and entertainment.” Anyone paying attention to the industry knows that this particular intersection is what’s keeping the lights on at most brands. The celebrity ambassador industrial complex has reached fever pitch, and if celebrities aren’t starting brands of their own, they’re surely endorsing at least one. Fashion houses need your attention as much as they need your money; how could they possibly earn the latter without the former in this economy? They’re required to entertain you, and it’s essential they put resources towards that goal. Back in 2021, Thom Bettridge wrote an astute Fashion Week take for Highsnobiety entitled “Fashion Is Dead, Long Live MerchTainment™,” which only rings more true today.
Gap has already reverted back to its pop cultural playbook that I remember vividly from watching MTV in the ‘90s — commercials that featured performances from dance troupes or musicians like LL Cool J, Missy Elliott, and Aerosmith against a sparse background — to great viral success, as seen with their KATSEYE denim campaign. But commercials and TikTok clips are only the tip of the brand-as-entertainment iceberg, and it’s a formula that’s already getting boring and oversaturated, so it will need to evolve. My friend Liana Satenstein is a master of this; her Neverworns Live! closet sales are a mix of performance (think Oprah on Adderall), educational programming, and shopping. Gap might be among the first to make a hire like this, but they will not be the last. Saks Group (Saks, Neiman Marcus, Bergdorfs) filed for bankruptcy protection last week, so the message is clear: If retailers do not figure out how to keep our attention, it’s literally life or death.
WhoWhatWear did their big one with that Elle Fanning cover. I have not seen so many of my colleagues and mutuals repost a fashion cover as much as this one in years. WhoWhatWear went artsy, crafty, quirky with this whimsical Elle Fanning cover, shot and creative directed by Szilveszter Makó — the same genius behind The Cut’s stunning Rama Duwaji cover story from December. In an industry that’s at the mercy of shrinking budgets, most shoots we get now, whether they’re sponsored or not, are confined to a studio with extremely limited personality. Makó’s work, meanwhile, is full of heart, character, and, of course, style that actually feels personal. Elle models the trappings of girlhood like hair bows and frilly dresses without seeming cliché; both of these Makó shoots are fantastical to me in the way Tim Walker’s were in the big-budget magazine heyday. It’s also no surprise that in the era of AI slop, the public is going gaga over these images that are undeniably human. More of this in 2026 please!
Dolce & Gabbana is back on its bullshit. The Italian house has a long history of being shitty, and they’re at it again. At the brand’s Fall 2026 men’s show in Milan over the weekend, the entire cast of models was white, or white presenting. C’mon, guys! Dolce still gets a lot of editorial and red carpet love because they have the cash to help secure these key placements; it’s always interesting when an otherwise progressive stylist conveniently “forgets” to tag D&G or turns off the comments when they dress a client in the brand. I get it, you have to pay the bills somehow! But at this point, there’s no way you can play ignorant about what Dolce stands for when choosing to work with them. The ever outspoken Bella Hadid (my girl!) even chimed in via Instagram comments, and she’s right:
While we are on the topic of problematic Italian brands… The first big stunt casting of the year (see? Fashion as entertainment once again!) came at the DSquared2 men’s show in Milan over the weekend, where “Heated Rivalry” star Hudson Williams made his runway debut. The Italian house’s show was ski- and winter sports-themed, making it a guaranteed home run for a viral moment. Unfortunately, as can be said for many Italian labels, DSquared2 designers Dean and Dan Caten have a track record of problematic decisions, ranging from stolen designs to cultural appropriation. I’m glad Hudson is getting his well-deserved bag, but I wish it was from a different brand. Gotta strike while the iron is hot, I suppose.
I want to be a friend of JW Anderson. If you’re a listener of my pod, I talk a lot about designers who use “friends of the house” in campaigns and front row moments as opposed to whichever A-listers or mega influencers they’re able to afford; this ties into the celebrity ambassador discussion above. In my opinion, no one does this as well as JW Anderson (aside from perhaps Thom Browne). He’s set himself apart by building out a cast of characters that not only feels “on brand,” but that also gives customers a sense of who he his and who/what he finds interesting. He takes chances on up-and-comers when many other fashion houses won’t, proven during his time at Loewe. For his eponymous label’s Fall 2026 look book, he cast the likes of fashion critic Tim Blanks, BMXer and musician Alice Temple, pop icon Kylie Minogue, and legendary stylist Camille Bidault-Waddington as models. This is the type of crew I’d love to sit with at a dinner party. More brands should take the time (and the potential risk) to figure out who really represents them and why — it’d make marketing feel infinitely less monotonous. You do not have to be everything to everyone!
I also really like Louise Trotter’s first Bottega campaign! Shot by Juergen Teller. I am very excited to see where she continues to take this.
From a point of view of someone who has 0 idea of fashion knowledge and its inside world your writing is like fresh air. Like sometimes I want to know more and be more curious about all of this but THERE IS SO MUCH INFORMATION!! So thanks and I really like your style. Bye :)
I feel like the 2016 stuff will stay a meme thing and won’t really materialize in fashion. A couple years ago people were trying to make “the new 2014” happen and that never took irl either, this stuff just isn’t far enough in the past yet for most people to be interested in the fashion and full beats again imo they just like remembering the internet culture of their youth. It’s not coming back in a real way until the older uncooler crowds stop wearing those styles.