With their coveted hair ‘dos and trailblazing sense of style, the free-spirited It Girls of the noughties were the women everyone wanted to be.
Sienna Miller’s boho fashion; Alexa Chung’s quick wit and effortless bob and Lily Allen’s edginess had fans clamouring to copy their every look.
And the ingénues’ lives seemed to be perfect – dating the hottest men, partying at the coolest venues and rubbing shoulders with the hippest people.
But behind the scenes, each has shouldered more than her fair share of heartbreak, betrayal and tragedy…
Pitched as Kate Moss 2.0, American-born Sienna, 38, made her modelling debut in the early noughties and soon became a member of the notorious Primrose Hill Set.
In 2004 she started dating Jude Law, 47, with the pair getting engaged that Christmas. But in 2005 Jude shocked by issuing a public apology for cheating with his nanny Daisy Wright while filming The Kings Men in New Orleans.
Meanwhile, Sienna was accused of cheating with her Layer Cake co-star Daniel Craig.
When rumours emerged they had an affair while the actress was still with boyfriend Jude Law, both initially denied it.
But Sienna later confessed to have being ‘briefly involved’ with the James Bond star, adding: "It was not a relationship, it was a very brief encounter, and he was my best friend.”
Jude and Sienna tried to mend their relationship but split in November 2006 and the following year she moved on with their mutual friend, actor Rhys Ifans.
But aged just 26, that ended when Sienna realised she wasn’t ready to settle down, apparently leaving the Welsh star heartbroken.
“I really thought I was very ready to settle down, but then I realised I wanted to be selfish for just a little bit longer,” she told LK Today in 2008.
“When I have a child, it will be probably become my whole life, so I don’t want to have any regrets that I should have done more. But I’m only 26, I have plenty of time.”
Her next romance derailed her glamorous free-spirited image when she dated married father of four, Balthazar Getty.
Apologising for her actions, Sienna admitted: “I have a good brain on me but I’ve never really used it when it came to making decisions about love, which has been a blessing and a curse.
“I probably seem like not a particularly nice person, not a girl’s girl,” she continued.
Then in 2011, the star settled down with English actor Tom Sturridge, 34, and their daughter Marlowe, seven, was born the following July.
But in 2015 they called off their engagement, again amid reports that Sienna didn’t want to commit.
"Tom wanted to get married and have more children. Sienna didn't,” a source told People magazine. “Everything exploded with Tom in London and Sienna leading a separate life in the US.”
In 2017 rumours of a fling with Brad Pitt swirled following his separation from Angelina Jolie . The pair were apparently seen getting cosy backstage at Glastonbury but Sienna refused to address the gossip, branding it ‘predictable and silly’.
She’s now dating art dealer Lucas Zwirner, 29, and has sparked rumours of an engagement with a diamond ring on that finger.
Before finding fame a 19-year-old Alexa was in a relationship with 40-year-old fashion photographer David Titlow.
Admitting the 21 year age gap didn’t feel strange but ‘probably should’, she was devastated when David ended things as her modelling and TV career began to take off.
“She had to go off and do her own thing,” he later told Vice, but Alexa, 36, begged him to reconsider.
"He said, 'I think it's time for you to go, Dolly. It was so sad," she told net-a-porter.
But he paved the way for her love affair with lead singers and musos, gifting her with a selection of music to live her life by.
"He was like, 'Here's all the cool music you need,' and with every boy after that, I've been like, 'Oh, you haven't heard of X-Ray Spex?'” she said.
In early 2007 she was casually linked to Klaxons keyboardist James Righton, who went on to marry Kiera Knightley.
But that same year she fell head over heels for Arctic Monkeys star Alex Turner.
They went public by snogging each others’ faces off at the Q Awards and Alex famously penned her that beautiful Valentine’s note she accidentally left in a New York bar.
It read: "My mouth hasn't shut up about you since you kissed it. The idea that you may kiss it again is stuck in my brain, which hasn't stopped thinking about you since, well, before any kiss.”
They relocated to New York when Alexa was offered an ill-fated job with MTV but split in 2011, leaving Alexa devastated.
“I’m not heartbroken any more, but I definitely was,” she told the Guardian two years later.
“I don’t want to imply he broke my heart. I was grieving for the loss of something… I’m grateful for the experience of that sh*t time, and for being on my own. I’d never really been on my own before – I’d always gone from one relationship to the next.”
A series of short-lived relationships followed, with Alexa linked to Coldplays’s Chris Martin and actor Jared Leto before she met Tarzan actor Alexander Skarsgard in 2015.
"He's an amazing man, very structured, responsible and supportive," she gushed to net-a-porter, hinting he had managed to tame her free-spirited ways.
But they called it a day in 2017 with Alexa telling Harper’s Bazaar: "I don't like being told what to do. And I don't want to be penned in. I don't want to feel I have to be anywhere… I am quite restless. It makes me a nightmare to date, I think."
She was subsequently linked to Jennifer Aniston’s ex Justin Theroux but is now dating chocolate heir Orson Fry, 24.
Lily was just 15 when she signed her first record deal, and by 19 she was an international star.
Desperate to be a mother and create a sense of stability after the tumultuous divorce of her own parents Alison Owen and Keith Allen, she often dated older men.
In 2008 Lily, now 34, announced she was expecting a baby with Chemical Brothers star Ed Simons, 49, but she tragically miscarried at four months.
They broke up soon after, and in 2011 she fell in love with builder Sam Cooper, 42.
With a ring on her finger, the loved-up couple left London to start an idyllic new life in the country, but their plans were derailed when their son George was stillborn at six months – a trauma Lily has said she will never get over.
“I held my child and it was really horrific and painful – one of the hardest things that can happen to a person … I nearly died. But I was numb and I didn’t care. I’d just lost my baby and that is a reflection of how numb I was,” she said.
She went on to conceive daughter Ethel, nine, closely followed by Marnie, seven, before announcing in 2016 that her marriage was over.
Admitting she’d suffered an identity crisis after becoming a mum, she confessed to cheating while touring in the States in 2015.
She told Vulture magazine: “I hired a team to dress me up with slick hair, nails, makeup; all harsh and pop star-y. I felt like I was in Alice in Wonderland. ‘Who am I? What is all this? What are these songs? Why am I nowhere near my children?’ Heh. ‘Where’s the vodka?'” she went on.
“I lost my sense of self. I lost my identity. I was being a bad mum. I was being bad at my job. I’d wake up on a tour bus in the middle of Wisconsin and be so hung-over.
“I cheated on my husband. All I wanted to do was be with my kids. I wasn’t even making any money. I lost my marriage, I lost my house, I lost my mind.”
She rebounded with grime MC Meridian Dan, but ended their relationship after yet another tour to the US in early 2018.
“I've just come back from a tour in America, which is where I was when things went wrong with Sam, and the same thing happened in my current relationship,” she told podcast How to Fail.
“I mean, I didn't take lots of drugs and have lots of sex with other people. I just became very lost.”
Lily is now dating Stranger Things actor David Harbour.
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