Every single person has to be fit from head to toe when doing a period show. [Fitting background actors] has to be so fast—20, 30 minutes max. When I fit the principal cast members it can take three hours. That's a good day. During my fittings with the actors, my assistant will take photos, and then I'll go see Matt and show him all the photos for each actor. We've worked together for five years, and he's always given me a lot of creative control. There aren't too many chefs.
I was in the process of making Betty's pink-and-white lace dress for Derby Day, and I had sent Matt a picture of Betty for January [Jones]. I hadn't finished the costume yet. I'd had a fitting really late with January. Matt called me really late, at 10:00, and the scene was to be shot the next morning. And he said, "Janie, I don't like this dress, it looks like a grandmother's." And I said "No, you do like this dress, it's perfect for this scene. It's romantic, it's everything you wanted for her first encounter with Henry, it's amazing." He said, "Just tell me it's going to be amazing." I was like, "It's going to be amazing." It was a costume I felt so confident about, but I really had to talk him into it. The next day I got a text from him, and he wrote to me, "January looks amazing! Thank you!" I was wiping sweat from my brow. But she really did look gorgeous.
For Joan's wardrobe, I've looked to Sophia Loren, Marilyn Monroe, Lana Turner, Jayne Mansfield—iconic actresses with that classic hourglass shape. Matt and I talked a lot about [her dress for the Season Five premiere]. I wanted to do something inappropriate for the office, more of a dinner dress or a cocktail dress. Sometimes Joan will wear kimonos, and I wanted to show an Asian influence with this costume as well. I wanted her to be the focus of the scene, so I went with hot pink, which is a little garish for that super bright white office.
Don Draper, his style is very understated, very minimal. He's all about being mysterious. For me, it's about creating a well-tailored man. His suits, sport-coats and trousers, they're always very well-tailored. Is his style going to evolve? I think we'll have to wait and see. But for so many, and also for Don Draper, those pieces he wears are also his uniform, and it really is based in the classics. Mainstream men's fashion didn't change that much until about 1967. Then you start getting into the wider collars and lapels and wider ties and bell bottoms, and then, going into the '70s, the full-on plaid, polyester leisure suits. But you still have this super minimal understated look from the late '50s through the mid- '60s.
I love the subtleties of men's wear. I love Don Draper's different cufflinks. I love that he wears his monogrammed "D" belts—he has four or five different belt buckles with his full initials. I love his ties, and how they've changed subtly throughout all five seasons. With [Roger] Sterling, I usually do a monogram on his shirts, and his three-piece suits and sock garters.
And I love the idea of the actresses getting dressed as women of the 1960s would, putting on their different foundations. It transforms them into their characters. They walk differently, they hold themselves differently, they feel differently in their costumes. It's all about how an outfit transforms the actors into their characters. That's so important to me.
–Janie Bryant, as told to Alex Hoyt