At first, there was no red dress. “Santino [Fontana] fought for that,” Tootsie costume designer William Ivey Long reveals. “In the movie, it’s almost a side thing showing Dustin Hoffman as Dorothy Michaels on the cover of Time magazine and then there he is with Andy Warhol. We don’t have that scene.” But they do have the dress.
Along with the sequined gown, Long designed two worlds for Tootsie—the musical itself and Juliet’s Curse, the musical within that musical—and earned a Tony Award nomination doing it (his second in 2019 alongside one for Beetlejuice).
READ: Why William Ivey Long Crafted Multiple Beetlejuice Costumes By Hand
Dressing Tony winner Santino Fontana as Michael Dorsey and the female alter ego he invents to disguise himself and get a job, Dorothy Michaels, Long scrutinized photos of today’s high-profile fashion for inspiration to make Tootsie feel contemporary. “I was looking through pictures of the Royal Wedding,” says Long, “and I see Meghan Markle arrive looking fantastic at her rehearsal dinner and she’s wearing an asymmetrical neckline and an asymmetrical hemline. I showed it to Santino and said, ‘You [as Dorothy] could have seen this Royal Wedding and thought, ‘I want that dress,’ and you’d look it up and they’re already copying it and making different versions, and they’ll send it to you. That Meghan Markle dress was the breakthrough moment.”
Long used Markle’s style as a foundation for all of his Dorothy dresses. The other “eureka moment,” as Long dubs it, was using Fontana’s physicality to a storytelling advantage. “Santino does not have a pronounced Adam’s apple. That allowed me to open up the neckline,” says Long. “You want an open neckline to feel vulnerable. Onstage an open neckline is very important for appreciating the human, the person.”
The red dress specifically was made on Fontana’s body. “I basically draped it on him,” says Long. “We safety-pinned fabric on him. We nipped in the waist, padded his hips and butt a bit.” Back in the ’80s, there was only one type of flat, shiny red sequins. To update the look, Long chose a specific shade of red and what he calls hologram sequins “because you can look into them. It just has more pizzazz and more zing-zang.”
Juliet’s Curse originally takes place in the Renaissance as the period sequel to Romeo and Juliet. “Dorothy Michaels didn’t want to be dowdy, she wanted to be glamorous, so she convinced the team and changed it,” Long explains of her motivations. In real life, the Tootsie writers looked to Long for what to change it to. “The writers came to me years ago and said, ‘If Dorothy Michaels is going to change it to make it more flattering, in what period will Santino look best?’ I thought about it and said, ‘The New Look by Christian Dior.’” Fontana’s broad shoulders make it work.
Long’s design inextricably links to the scenic design by David Rockwell and lighting design by Donald Holder—especially when it comes to Dorothy’s vibrant palette. “I call them the colors of the kingdom,” Long explains. “All of Dorothy Michaels' colors are in the scenery, in those buildings around her. When the pin spot [lights] come in and you see just Dorothy Michaels, Donald Holder accentuates the colors of those buildings to support whatever dress Santino is wearing for that particular soliloquy.”
Color also comes into play in building Tootsie’s other characters. For Sandy, “I just knew we needed mismatched wacky,” says Long.
[SPOILER ALERT] He even uses costume to foreshadow the relationship between Jeff and Sandy. “His plaid shirts always relate to her dress,” says Long. “They’re simpatico. There’s a sympathy because the colors connect.”
For Juliet’s Curse director-choreographer Ron Carlisle, Long decided on black and gray with a dash of plum. He also custom-made suits and pants for the austere man of the theatre.
Rita Marshall, the producer of Juliet’s Curse, was inspired by the time Long worked with actor LInda Lavin and she wore her natural white hair. “I dressed her in oyster colors, which you don’t think of dressing people with white hair in oyster colors,” says Long. “Shimmery silver, shimmery copper, colors of pearls. She always has a little Lurex because she’s that person.”
But Long grounds his design in Lilli Cooper. “I first started by looking at how did she dress herself on the red carpet?” Long says. “What does she wear to the opening of SpongeBob the Musical, which she starred in? What does she wear to other people’s shows? How does she like to look?” Tootsie earns its 2019 stripes with Julie and the contemporary dress that projects her confidence and comfort in her own skin.
When it comes to the women of Tootsie—Dorothy or otherwise—Long wanted “flirtatious and strong.” Well, it is the clothes that make the woman.