The first time I saw Anna Wintour in the flesh, I was walking through a parking garage that connects 43rd and 44th Streets, near the old Condé Nast offices in Midtown. I was new to the company and had lived for a few weeks in fear that I would accidentally encounter Wintour in an elevator and would have to scurry out, as was the rule (I was told). But instead there she was, walking the other direction all alone, unattended by any frazzled, starry-eyed assistants. She caught me gawking at her and gave me a friendly nod, those enormous dark sunglasses dipping down briefly, and that was that.

It was small confirmation, somehow, that I had indeed arrived at a fancy place. I didn’t work at Vogue, but Vanity Fair was close enough, especially for someone raised in the blog mines. Us younger writers on the come up were then supposed to be pooh-poohing legacy media, preening dinosaurs all, but it was impossible to not feel excited and glamoured by the lingering sophistication of it, even if it was fading. I’d arrived just in time to see the last glimmers (which are somehow still glimmering, almost 13 years later), thought I knew that I had missed the party when it was in full swing. 

After all, the wallpaper was already peeling when, seven years before my parking garage encounter, The Devil Wears Prada made grand, aspirational fantasy of the magazine world—specifically that of Condé Nast. The film’s unflinching insistence that a magazine editor could hold all the keys to the kingdom was willfully naive to the intrusions of the internet, and of course unaware of the coming social media epoch that would disastrously erode the clout of a magazine like Vogue. I always enjoyed watching the movie, which is given such sparkle and pep by director David Frankel and a sterling cast. But revisiting it (as I often did) grew increasingly melancholy, becoming ever more of a journey to a distant past when hallowed institutions (frivolous and cruel as they could be) still mattered. 

In 2026, the movie feels almost as ossified and faraway as anything in an Edith Wharton novel. All that haughtiness, that sureness of position, seems so ignorant. Miranda Priestly, the Wintour stand-in played by Meryl Streep, seems dumber than she does savvy; how could she, such a trendsetter, not see the future coming? And how could smart, ambitious wannabe journalist Andy (Anne Hathaway, in arguably the last of her Mia Thermopolis roles), not reportorially intuit that the life she aspired to was disappearing in front of her? 

There was also a strange side-effect of the movie’s cultural presence, a kind of gloomy frustration when people would, here and there over the years, excitedly ask if life at Condé was anything like the movie. Not really, I would respond chirpily, not wanting to say that, actually, we were scared for our jobs all the time, that most of us had missed the movie’s version of things by a number of years. I didn’t want to dispel what was vivid in their imagination, which made the reality sting all the more. 

So when a Devil Wears Prada sequel was announced, I bitterly scoffed. Because, yes, fan-service sequels are, in general, a scourge on the filmed arts (sorry, Frisky Summer 3). But really because I figured, what could they possibly show? Layoffs and downsizing, shrinking offices and dwindling resources? That would be awfully depressing. I assumed, then, that the movie would mostly lie to its audience, that it would acknowledge some of the media landscape’s changed circumstances, but that it would keep things elevated above the gloom of the hard truth. 

To my surprise, the new film (out now) is actually pretty blunt about what has befallen magazines and newspapers since the original movie was released. DWP2 opens with Andy, now a respected journalist covering a variety of beats, learning that she and all of her colleagues have been laid off from their paper—while at a ceremony receiving awards for their work. It’s a dire (and all too conceivable) note to begin on and the rest of the film pretty much follows suit.