It was the picture we never thought we would see: Paris Hilton hiding underneath a blanket, actually trying to avoid the paparazzi. Where was her signature over-the-shoulder smoulder, that smug girl-who’s-got-everything smile or the always-possible up-the-skirt shot of her fresh bikini wax? This was a look we hadn’t seen Hilton attempt before.

It seems the heiress, who has made a career out of reality shows and celebrity hook-ups, finally had something on her mind: she had just left her lawyer’s office and been told that, despite his best efforts, she was going to jail. Hilton had been sentenced to 45 days in a women’s prison for violating her probation for a drink-driving charge. Due to overcrowding and good behaviour, she will serve a minimum of 23 days, which will probably be the longest time she has been separated from a pair of hair straighteners in her entire privileged life.

Hilton’s real talent has been turning scandal into gold. When a raunchy sex tape hit stores, she used the subsequent publicity to drive up ratings on her reality show, The Simple Life. Even after outrageous videos showing Hilton making racial slurs were found in an abandoned storage locker earlier this year, she hopped on a plane to Vienna to pick up a reported million-dollar pay cheque merely to attend a gala. Indeed, throughout her career, it hasn’t mattered if it was good or bad press; Hilton, to steal from her own vernacular, was “hot”.

But on June 5, when she trades in her Gucci handbag and Louboutin heels for an orange jumpsuit and government-issue flip-flops, her biggest career challenge to date will commence: can the expert image-maker find a way to put a positive spin on doing time?

Certainly not, if any of the feud-friendly socialite’s peers have anything to do with it. At a dinner in Miami a few weeks ago, starlets Hilary and Haylie Duff reportedly toasted Hilton’s sentence. And a member of a rival celeb’s camp in LA was heard to crow: “We’re all hoping somebody knocks some sense into that bitch when she’s there.”

Poor Paris. The Century Regional Detention Facility in California is hardly a Hilton resort: gangsters, drug dealers and prostitutes inhabit much of the compound. Hilton has already received death threats and is, apparently, taking self-defence classes. Not that she will need them. Even in jail, she will receive the velvet-rope treatment. According to reports, Hilton will be segregated from the other prisoners for her own protection and housed in a “special-needs unit”.

But what really matters to Hilton and the industry she has built up around her is the way that she is perceived. So how are she and her advisers – a cabal of publicists, lawyers and immediate family – going to handle the delicate matter of her image at this difficult time?

Following the verdict, Hilton endorsed an online petition to Arnold Schwarzenegger, the governor of California, appealing for a retrial, on the grounds that “this sentence was both cruel and unwarranted. I don’t deserve this”. But when it became apparent that her celebrity connections would not get her off, she changed tack completely. She released a statement saying: “Nobody is above the law. I surely am not. I do not expect to be treated better than anyone else who violated probation. However, my hope is that I will not be treated worse.”

This hint of persecuted martyr may well work in her favour. “By making herself the victim,” says one publicist, “she can gain public sympathy, pay her debt to society and come out a changed woman.” Hilton played up the penitent pose, appearing in public wearing modest clothes and looking contrite and concerned. The new plan was clearly to distance herself from the pampered, princess-above-the-law image, and sell herself, instead, as any other driver who makes mistakes, albeit a far richer, blonder and prettier one than most.

This is where Hilton’s prison look will play a role. While the thought of being without fake eyelashes and a twice-weekly mani-pedi is undoubtedly causing her to toss and turn at night, even more than the prospect of prison food and the confiscation of her mobile phone, any long-range paparazzi shots of a wan Hilton sweeping the yard or sewing hessian sacks will do much to win public sympathy.

Will it be enough? Some say no, including David Patrick Columbia, a friend of the Hilton family and chronicler of New York society. “Drunk-driving is a serious crime,” he says. “People die from it. Jail is a whole other ball game from the soap opera we’ve enjoyed watching up until now. I think we could be witnessing the end of Paris Hilton.”

Others, however, say yes. What she will temporarily lose in gloss, they claim, she will more than make up for in notoriety. In fact, some of her closest supporters are convinced a spell in the slammer is just what Hilton’s career needs to take it to the next level. “Prison will be the best thing that ever happened to Paris Hilton,” says the fashion designer Alvin Valley, one of her closest friends. “It’s going to make her more famous than ever,” says another friend, who thinks the Porridge look will suit her. “In jail, she’s going to get enviably skinny, and without any make-up or products her hair and skin will finally be able to breathe, so they’ll look amazing, too. Plus, she’s going to get all that street cred.”

Not to mention fashionability. People are already anticipating her comeback. After all, Winona Ryder parlayed her chic court appearances (she was on trial for stealing designer clothes from Saks Fifth Avenue) into a Marc Jacobs ad campaign; and a spell in jail didn’t do Martha Stewart’s career any harm, either. “Serving time is chic, these days,” says Douglas Perrett, a New York-based casting agent and blogger.

Indeed, Hilton will have all the fresh media material she could ever wish for. Her prison diaries would be a bestseller, or maybe she could make a self-defence workout video based on the moves she learns under lock and key. So long as she manages to get her hands on some fresh hair extensions and false eyelashes before the all-important, first postrelease paparazzi shots, perhaps everything will be all right, after all.

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