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'Heartbreakers' 15th anniversary: The best outfits

Fifteen years after Sigourney Weaver and Jennifer Love Hewitt conned their way to love and money, one of the film’s costumers dishes on the movie’s best looks.

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Everett Collection

Fifteen years ago Wednesday, Heartbreakers opened to mixed reviews (EW gave it a C+) but debuted at No. 1 at the box office and went on to make more than $57 million worldwide. Directed by David Mirkin (Romy and Michele’s High School Reunion, The Simpsons), it starred Sigourney Weaver and Jennifer Love Hewitt as a mother-daughter con-women operation, telling the story of two women who get off on duping men into handing over their paychecks and refuse to fall in love for real … until they do.

Now more than a decade later, its hijinks — Dump glass into a salad to get a free meal? Classic! Spill water in a hotel for a comped penthouse? Genius! — help the movie hold up as a silly, subversive comedy worth re-watching.

But the outlandish outfits and over-the top costuming keep Heartbreakers firmly planted in the early-’00s, where miniskirts, chunky heels, lacy bodices, and Betsey Johnson dresses assist Max (Weaver) and Page (Hewitt) in screwing over potential husbands. “The women are in control,” Cathie Filian, who served as Hewitt’s costumer on the film, tells EW. “They controlled not only with their brains, but they controlled with what they wear. When they put on their outfits for grifting, it’s like they’re putting on a costume or a work uniform.”

Ahead, Filian details some of the best style moments from Heartbreakers.

Max’s wedding night lingerie

 

In one of the first introductions to Sigourney Weaver’s Max, viewers see a recently married women who goes by Angela ready to seduce her new husband Dean (Ray Liotta). Fresh off a wedding, they can’t wait to get to bed — she’s abstained from sex until marriage, she says — and when she takes off her wedding dress, she reveals a pale blue lace bodysuit, complete with a corset, tights, and arm detailing. “It cost a fortune,” Filian tells EW. “It was handmade, custom-made for her. Seeing her in it in real life, it was unbelievable. The way she wore her different looks and how she would take ownership of that look for her character was pretty cool.” Too bad new hubby Dean cuts the whole thing up just before Angela falls asleep.

Page’s teeny tiny grey dress

Used as a pawn to con Dean, Page (acting as his assistant Wendy) wears a minuscule gray dress with a deep neckline. “Most things don’t come that short,” Filian says. She ended up hemming most of Hewitt’s dresses, many of which were purchased off the rack from department stores like Macy’s, inches above where they had been originally. “I saved all the hems we cut off her dresses and I would sew them into purses for her to keep at home. There was literally that much fabric leftover.”

All the “normal” clothes

There are only a handful of scenes in the film in which Max and Page are being Max and Page, not the duplicitous versions of themselves. “When they’re being themselves, we have them in casual looks,” Filian says. “When Page is grifting, she’s wearing outfits that are a joke of what you think is a sexy outfit. They’re cartoonish.”

Page’s pink dress

Page wears a tight, pink dress for a night out in Florida where she meets bar owner Jack (Jason Lee). Everyone in the bar — including guest stars Sarah Silverman and Zach Galifianakis — is wearing casual street clothes, but Page, on a mission, is dressed for a New York club. Filian says they filmed the scene in Florida’s Everglades where the mosquitos were rampant. “Her legs were covered in mosquito bites — someone from the crew even had to go to the hospital because the bites were so bad — but we wanted her to wear this dress in the Everglades, near real baby alligators, real snakes.”

Page’s French maid costume

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Everett Collection

While Max is trying to con William Tensy (Gene Hackman) she disguises herself as Ulga, a sultry Russian, and has her daughter play a French maid who attempts to tease him. “That was a Betsey Johnson dress,” Filian remembers. “We added some trim to it, altered the bustline and shortened it quite a bit if you can imagine. The key to all of these dresses were foundation garments and double-stick tape.”

Page’s wedding dress

After Page (as Jane) successfully cons Jack into proposing and marrying her she realizes her real feelings for him. When it comes to picking out a wedding dress, she subverts into her real persona. “That dress was specific because we wanted to go with something that was — and this was in the script — sweet, traditional, not overtly sexy,” Filian says. “She did love him at that point and it was conflicting for her. It’s the complete opposite wedding outfit we see her mom wear in her wedding to Dean.” Filian says they bought the dress at a bridal store in the San Fernando Valley and that it “wasn’t too expensive, compared to what wedding dresses can be.”