They are shown shopping and gossiping in a series of luxurious locales such as: London, the Hamptons, Hilfiger's family estates in Nantucket and tropical British West Indies, as well as Los Angeles.

[1] Notable cameos that occurred during the program included American Idol judge Randy Jackson who ran into the girls at a Los Angeles eatery, former President of the United States Bill Clinton who attended a special screening of the World War II film Proud (a project Hilfiger produced) held aboard the Intrepid Sea, Air & Space Museum, and Ally's famous dad, who invited his daughter to his workplace to critique his junior's line.

A total of ten episodes were produced during the season, and included one that featured the Northeast blackout of 2003, which had a direct impact on the series, as the production was taping in New York at the time of the event.

After the season ended, Ally continued using marijuana for her illness many months before being placed in rehab by her parents where she was eventually properly diagnosed with Lyme disease.

The program's theme song was "This Town", an edited cover version of a track from The Go-Go's 1981 debut album Beauty and the Beat and performed by the all-female Canadian pop/rock group Lillix.