The inaugural Hats for Hope event was held on April 7, 2004. The event was located at Gardencourt, and lasted from 6-9 p.m. With the purchase of a single ticket, individuals enjoyed hors d'oeuvres, drinks, and a DJ.

There were more than 300 people in attendance, enjoying everything this event had to offer. Designer, celebrity, and gently worn hats were bid on and purchased throughout the night. There were also several non-hat items offered. Some of the items auctioned at the event were: Chicago Get-A-Way Weekend, 2 tickets to Jockey's Gala Kentucky Derby, and a dinner/show/overnight stay at Glassworks & Jazz Factory.

Hats for Hope raised approximately $13,000 for the American Cancer Society, and designated the money to support the same research as the funds raised from the Making Strides Against Breast Cancer event.