Forget designer bags or cushy cribs, for the next few weeks Lohan will be sporting the jail-standard orange jumpsuit and sleep on a vinyl mattress in a 12X8 foot cell. For her own protection, she will be isolated from other inmates.
According to a former inmate, today will be the worst for the young starlet.
"It is something you will never forget," former inmate Tanya told "Good Morning America." "When you get strip searched it takes away a lot of dignity. You are not in a room by yourself."
But ABC News legal analyst Dana Cole said that for most of her time behind bars, Lohan will just be bored.
"It's not going to be the worst situation imaginable, far from it," Cole said. "It's just going to be boring basically."
Lohan is set to appear in court today for a short hearing after which she is expected to be taken to the Los Angeles County Women's Jail.
Report: Attorney Shapiro Ditches Lohan
Lohan will be making her court appearance without the representation of high-profile defense attorney Robert Shapiro who recently joined the case, the Los Angeles Times reported today citing court documents.
Though Shapiro would not comment on the split, Cole confirmed a closed-doors meeting between Shapiro and the judge took place Monday.
"He probably said [to Lohan], 'Listen, if you're not going to do it my way, you can go do it your way but you're going to twist in the winds alone," former prosecutor Robin Sax told "GMA" today. "It's not surprising that Robert Shapiro has had trouble holding Lindsay under control. That's been a big problem from my sources and what I hear... in terms of getting her to actually succumb to the process, realize she has a problem and actually listen to the orders."
In a statement earlier this week, Shapiro said he "agreed to represent Ms. Lohan on the condition that she complies with all of the terms of her probation, including a requirement of jail time."
Lohan was spotted at a rehabilitation facility that Shapiro owned where he planned to implement "a treatment approach recommended by medical professionals for Ms. Lohan's long-term recovery and sobriety," the statement said.
Sax said her reported split with Shapiro shouldn't have much of an effect on Lohan's jail time.
She is scheduled to be released from jail just in time for the premiere of her newest movie, "Machete," in which she plays a gun-toting nun.
Expert: Jail, Rehab Would Be 'Best Thing' for Lohan
Though Lindsay may have broken out in tears when she was handed down the jail sentence, an addiction expert told "GMA" Monday that jail time and rehab could help the starlet take a turn for the better.
"It's the best thing that can happen to Lindsay because frankly, she's running out of options," William Moyers, vice president of the Hazelden Foundation, said. "She should have as much opportunity to recover as anyone else, but often times for people it's the consequences which include jail time that allows them to wake up and take that personal responsibility to live a life of recovery."
For better or worse, celebrities are no strangers to stretches behind bars.
Starlet Nicole Richie battled a heroin addiction before she was sentenced to four days in jail. Though she only served 82 minutes, Richie bounced back by starting a family and launching a clothing line.
Charlie Sheen's acting career has been coupled with decades of substance abuse and several stints in rehab. But even after years of treatment, Sheen spent this past Christmas in jail for assaulting his wife. He's also currently awaiting sentencing and could face several years in prison.
Paris Hilton famously served 23 days in jail in the summer of 2007 following a DUI conviction and driving with a suspended license. Three years later, Hilton is reportedly back in trouble with the law after she was detained and then released on the French island of Corsica this weekend accused of marijuana possession, according to French newspaper Corse Matin.
"Lindsay's jail sentence will be very similar to where Paris Hilton went," US Weekly senior editor Ian Drew said. "She will have a very sanitary living condition. It will be very white washed, very simple, very plain."
Lohan was sentenced to 90 days in jail in addition to 90 days of in-patient rehab in early July for violation of a 2007 probation she incurred after a DUI conviction.