Britney, Paris, Kim. Poor Jen, messy Lindsay, talented yet tragic Amy. If you were an even vaguely young woman in the 00s, these celebrities’ first names alone probably conjure memories. They were our cultural wallpaper, female icons made and too often broken by mass media, in whom we hunted “for clues about what a woman ought to be”, as the journalist Sarah Ditum writes. Sexy, but not too sexy; empowered, but still unthreatening. Ditum’s hotly anticipated book brilliantly captures the prevailing millennial mood of anti-nostalgia, or looking back through newly appalled eyes on the past – in this case an era of prurient, tech-enabled misogyny she christens the “Upskirt Decade”, elastically located between 1998 and 2013. “I lived through the noughties. I read the blogs. I laughed at the jokes,” she writes. “And yet, in writing this book, I haven’t felt like I was revising familiar territory. I have felt as though I were entering an entirely alien landscape.” The nine modern feminist fables here are perfectly timed for readers still blinking in disbelief at what Russell Brand got away with saying about women in broad daylight so very recently, but she’s surely right that this mood of reckoning dates back to #MeToo and the way it encouraged so many women to re-evaluate their own pasts. Her thesis – that toxic celebrity culture hurt both celebrities and ordinary women encouraged to make “sense of our own existence” through these manufactured stories – was one I couldn’t wait to read. Those two ideas are best combined in the first essay, on Britney Spears. Ditum was 17 and Spears 16 when …Baby One More Time came out; the author soon had a poster Blu-Tacked to her bedroom wall. Only slowly did it become clear how little power Britney really had. The private act of losing her virginity was treated, Ditum writes, as a public event “for which she owed the nation an apology”, even as Britney’s boyfriend Justin Timberlake was lionised for getting her knickers off. Here was the double standard – women diminished by sex, men enhanced – writ large, in a grim lesson to all the girls with posters on their walls. The story of Paris Hilton, the partying heiress devoured by gossip bloggers, is equally cleverly rendered into a story about how porn went mainstream. In 2004, the sex tape a 19-year-old Hilton had made with a boyfriend leaked online to widespread hilarity. Who cared if she hadn’t consented to the world seeing her naked? Hilton was a “rich bitch”, a woman even other women felt comfortable hating. Only much later, after revealing she’d been sexually abused in her teens, was Hilton eventually seen with some compassion – though as Ditum shrewdly notes, encouraging women to volunteer their trauma for public entertainment maybe isn’t the progress it seems. She’s terrific, too, on the way Jennifer Aniston’s battles with infertility were held over singletons as a scare story about successful women supposedly missing out on love and babies. And beneath all this runs an interesting backstory about how structural changes in the media industry – from the rise of blogging to the way reality TV ate pop music (somewhat awkwardly weaved into Amy Winehouse’s chapter) – shaped female lives. Unfortunately, when reaching for deeper cultural relevance, some of these essays begin tripping over themselves. A chapter describing former child actor Lindsay Lohan’s descent into alcoholism unwisely attempts to tie her story into the defining terrorist atrocity of that decade. (Broadly, the argument appears to be that in 2006 Lohan made a bad romcom set in New York that didn’t mention the twin towers attack and flopped commercially, somehow making her an illustration of “how the United States was floundering as it tried to come to terms with 9/11”.) Similarly, Ditum notes that Kim Kardashian’s escapist reality show took off after the banking crash but seemingly then doesn’t know where to take this economic argument, while I wondered how many 00s women genuinely did live their lives through the professional TV wrestler Chyna (even Ditum calls her legacy “hard to pin down”). The book concludes in upbeat mode, with uproar over the “rapey” lyrics of Robin Thicke’s song Blurred Lines and the seemingly unstoppable rise of Taylor Swift deemed to mark the end of a lousy era. Instagram, Ditum argues, let women such as Swift leapfrog the media and engage directly with fans, helping ensure “the casual cruelty of the noughties no longer had a place”. Yet some fans’ furious reaction to Swift’s recent choice of boyfriend suggests that cruelty may have merely evolved. Was fame easier back when Heat magazine was bitchily highlighting your cellulite, or now, when anyone can point it out to you directly on Twitter, in among the death threats? But perhaps that’s the real message; that every generation unwittingly creates something the next will eventually regard with horror. Let the perfect book not be the enemy of what remains a damn good thesis. Toxic: Women, Fame and the Noughties by Sarah Ditum is published by Fleet (£22). To support the Guardian and Observer order your copy at guardianbookshop.com. Delivery charges may apply