"She looked gorgeous and seemed in high spirits," said an onlooker. "She was smiling and playing coy with the paparazzi."
Hilton has until Tuesday to begin serving a minimum of 23 days at the Century Regional Detention Facility for violating probation.
Sheriff Lee Baca, whose department oversees the facility in Lynwood, Calif., where Hilton is to do her time, said the actress will not be allowed to "be seen in handcuffs -- or in the back of a police car, forlorn and in handcuffs."
"Jails are not circuses and not places where 'fun' is the priority," Baca said. "Jail should be a corrective learning experience."