Chessie’s wardrobe from The Parent Trap is still being recreated by devoted fans more than 20 years later, but Lisa Ann Walter wasn’t thrilled to wear the iconic outfit.
“Elaine [Hendrix]’s appearance was all about the cut of the dress and how many dresses she had to try on to find the perfect white with a black hat over which she raises her head. It was all very, very thought out. And the beige one that Natasha [Richardson] wore. She was very practical about all of this, including mine. I’ll be honest. I can handle it when I’m a jerk. I struggled with this big closet with all my might.”
Walter didn’t like baggy pants, a purple top and a denim button-down shirt. “She was the director, and I didn’t say: “I don’t want to wear this.” I was just saying: “You can’t see my waist.” And I’ll tell you why,” she said. “All my life I have been a difficult child at school. I’ve always been. They teased me mercilessly. I would get into fights. I came home in tears. I had a real problem with the fact that I’m not attractive if I’m heavy. …So it was a struggle inside of me. It had nothing to do with the wardrobe or anything else. Nancy’s idea was right. As we see today. It’s become a wardrobe for this younger generation and for a group of moms, and I really appreciate [it].”
The Abbott Elementary actress was handpicked for the film by costumer Penny Rose, who she says is “one of the most elegant women” she has ever met. She would also have realized only 15 years ago that her “battle” with wardrobe choices “was internal.”
“To some extent, I was a pain in the ass,” she joked to us. “Therefore, I will publicly apologize to Nancy. She was right about everything. And you know, it was like, “Oh, purple. I don’t like purple.” The fact is that he is big, and I don’t show my waist.”
Walter played nanny Holly Parker (Lindsay Lohan), who lives in her vineyard house in California, in the comedy, which also starred Dennis Quaid as Hallie and Annie Parker’s father, Nick Parker. And, according to Walter, Chessie’s appearance made sense so that viewers wouldn’t get confused about her platonic relationship with Nick.
“[Nancy] was right about how to balance the film. I can’t run around — because I’m very busty. But really, Dennis, he’s such a naughty boy. But one day he told me — because I was always trying to apply more mascara, I like glam. I’ve always been a disco girl, overly made up, with shiny eye shadow. So it’s much more downplayed. They dyed my hair from what was, what looked like long strands, to, as Nancy said, damn brown,” she recalled to Us. “And one day in the makeup trailer, I was trying to apply another layer of mascara — and [my makeup artist] slapped me on the arm with mascara and said: “Stop it!” And Dennis came up behind me, and he looked in the mirror next to me, next to my face. And he says, “You know, if you looked as cute as you do in real life, everyone watching the movie would say, ‘Why doesn’t he just pop into the kitchen?'”
“So, for me, that said it all,” she said. “And as a writer, I am, yes. A lot of people thought, “Oh, is that his sister?” Like, there should be no confusion with this sexual energy. Because people had to understand who is who and who we are rooting for. And so I thought, “Yes, yes, I get it.” It was good.”
Quaid, 67, and Walter also shared a nice moment while filming an emotional scene in which Chessie finds out that Halle is actually Annie.
“It was a rather unusual moment in my acting career. It was meaningful, and there’s a reason why people react to it,” she explained to Us. “For this scene, I used what they call a doorstep job, taking an emotional journey to a time when my daughter, my second child, had just been born. We just bought a house. Three weeks after she was born, we moved into my first home in New Jersey. We could barely make [our] mortgage. I had to go back on tour as a stand-up. …And I took care of her, but I pumped her when I was on the road. … I’d run back to the hotel between sets and take care of her, and then come back for the second show. But many times I flew across the country or went to Buffalo, got on the train, and then got in the car, and she was a five—week-old baby. And all I’ve been in my adult life is a mom. And I’d just grab her in the backseat, from the car seat, and just sniff her head. I wouldn’t let her down. Or the second I entered the house, I smelled her from her room, because we are mammals. What I had to go through to leave her as a baby was so hard.”