Hollywood stars, historical footage and stylized reenactments tell the story of costume designer Orry-Kelly, who ruled Tinseltown fashion for decades.
| Actor | Role |
|---|---|
 Orry-KellySelf (archive footage) | Self (archive footage) |
 Darren GilshenanOrry-Kelly | Orry-Kelly |
 Deborah KennedyFlorence Kelly | Florence Kelly |
| LLouis AlexanderYoung Orry | Young Orry |
 David E. WoodleyWilliam Kelly | William Kelly |
| NNathaniel MiddletonThe Lover | The Lover |
 Lara CoxGinger Rogers | Ginger Rogers |
| KKelly Ann DollShowgirl | Showgirl |
 Ann RothSelf | Self |
| JJean MathisonSelf | Self |
 Angela LansburySelf | Self |
 Jane FondaSelf | Self |
| SScotty BowersSelf | Self |
| EEric ShermanSelf | Self |
| MMarc EliotSelf | Self |
| WWilliam J. MannSelf | Self |
 Catherine MartinSelf | Self |
| DDavid ChierichettiSelf | Self |
 Leonard MaltinSelf | Self |
 Deborah Nadoolman LandisSelf | Self |
| MMichael WilkinsonSelf | Self |
 Kym BarrettSelf | Self |
| LLarry McQueenSelf | Self |
 Colleen AtwoodSelf | Self |
| BBarbara Warner HowardSelf | Self |
| JJune Dally-WatkinsSelf | Self |
| JJanet FowlerSelf | Self |
 Ted MaynardJack Warner (voice) | Jack Warner (voice) |
 Jeanette CroninBette Davis (voice) | Bette Davis (voice) |
 Tyler CoppinWalter Plunkett / Jimmy Fidler / Sergeant (voice) | Walter Plunkett / Jimmy Fidler / Sergeant (voice) |