The pairing of Cary Grant and Katharine Hepburn most likely brings to mind The Philadelphia Story (1940) or Bringing Up Baby (1938). But Holiday (1938, directed by George Cukor) is possibly my favorite. It's the story of Johnny (Grant), a self-made man who has proposed marriage to heiress Julia. Johnny wants to quit working so he can travel and experience life. Julia can't understand why he doesn't want to just make more money, but her sister, Linda (Hepburn), a fellow free spirit, understands Johnny completely. You can imagine what happens next.
There are some lovely late 1930s fashions in the film. A New Year's Eve/engagement party showcases some evening wear, but I really enjoy seeing the daily outfits and shoes (and wild hats) the sisters wear.
Linda is usually dressed a bit more simply and less flashy than Julia, though still always very elegantly. I prefer Linda's black satin dress here.
Hepburn is dressed in a simple black gown for the party, but wears a necklace that sparkles more than anything I have ever seen captured on film. I really think Cukor used some kind of special effect for the glittering jewels on this necklace.
I love this scene. Ned (Lew Ayres), the sisters' hard-drinking, frustrated musician brother, marches in with champagne. Ayres plays this role with the perfect mixture of humor and pathos.
Grant and Hepburn perform some fantastic tumbling moves in the film.