Mad Men costume designer Janie Bryant has the best job on earth. Since costumes are such a big part of the show, her role is not only fun, it's absolutely essential to creating a vivid world.
Outfitting such the diverse set of characters has its perks — dressing Betty in that bright pink nightgown insanity was a stroke of genius — but as the show transitions into the late 60s, Bryant has the challenge of modernizing the classic cast.
On Joan's fly purple vest in the season 6 opener:
That is one of my original designs. When we left Season Five, Joan had gotten a new income and new position at the office. Considering that, and everything that was happening in her personal life, I really wanted to give her an update. I designed the purple blouse, skirt, and vest for her. I think it spoke to the masculinity of the office but the femininity as well. Instead of designing a suit, it was a vest and a skirt, with an A- line, so it has a little bit more of a modern feel. It is still body conscious, but the vest is traditionally men’s wear, so it was nice to balance those two things.
As for the dudes, Harry's look was inspired by Rosemary's Baby!
That was definitely an inspiration from Rosemary’s Baby. [Laughs.] There is a scene where Rosemary is talking to her older neighbor [Roman Castevet, played by Sidney Blackmer], and he is wearing this checked jacket. I saw that and thought, “Oh my God, I want to do that for Harry!” I watched Rosemary’s Baby so many times, that was another big inspiration for me.
And what about getting everything to Hawaii?
Well, we prepared here in Los Angeles but had to ship all of the costumes there. We had five days of fittings [in Hawaii] to fit the background actors and also check fits for the principal cast and the dancers at the luau. We had to build all of those costumes. In Hawaii, we worked with the dance choreographer there, and she had all of the accessories, including the headdresses, made for me when we were in Hawaii. I am just so thankful for my crew. That was not only a huge accomplishment for me and my department but for the art department.