This week, Chelsea challenged a part of Ivanka's convention speech that proposed things her father would do for equal pay, reports CBS News correspondent Julianna Goldman.
"As president, my father will change the labor laws that were put in place at a time when women were not a significant portion of the workforce and he will focus on making quality childcare affordable and accessible for all," Ivanka said.
Chelsea bluntly weighed in when asked about those remarks during a Facebook live event with Glamour magazine.
"How would your father do that given it's not something he's spoken about, there are no policies on any of those fronts that you just mentioned on his website," Chelsea said.
"They are both highly impressive," said Joanna Coles, editor-in-chief of Cosmopolitan magazine. "Ivanka, in particular, is being used to make her father more attractive to women voters at the moment who we know at the moment, don't find him appealing. Chelsea also has a challenge because we know that young female voters were really compelled by Bernie Sanders."
Throughout the campaign, the two women have been their parents' biggest supporters and defenders.
"She proves again and again why she should be our next president," Chelsea said of her mother on "CBS This Morning" last year.
"Look, I'm not in every interaction my father has but he's not a groper," Ivanka responded to a claim that her father had groped his former colleague during a business meeting.
The common threads between the famous daughters transcend politics and the corporate world, where they both hold leadership positions at their family firms - the Clinton Foundation and the Trump organization.
"They both live in New York . Their husbands actually know each other," said Helena Andrews-Dyer of the Washington Post. "Ivanka is a working mom like Chelsea is a working mom they're both Ivy League grads."
But according to Andrews-Dyer, Trump and Clinton are different in a crucial way.
"Ivanka was a model as a young woman, she was on her father's television show. Chelsea, on the other hand, was sort of thrust into the public sphere and she's been living sort of a private public life for many, many years," Andrews-Dyer said.
Last September, Chelsea spoke about her friendship with Ivanka.
"Ivanka and I talk about everything, as I'm sure... you do with your friends," Chelsea said.
When Chelsea addresses the Democratic Convention Thursday night, she will be able to show a different side of her mother, as both a mother and a friend.