Everything We Know About Karlie Kloss and Ivanka Trump’s Relationship

Karlie Kloss and Ivanka Trump are sisters-in-law. Did you forget this? Karlie Kloss might be hoping you forgot this, but Ivanka Trump wants to remind you at every opportunity. Which is awkward, to say the least.

Karlie, the 26-year-old supermodel, married Josh Kushner, brother of Ivanka’s husband, Jared Kushner, in a quiet ceremony in October 2018 after a five-month engagement and six years of dating. (Go read our comprehensive timeline of Karlie and Josh’s relationship. Seriously, you won’t regret it.)

On Karlie’s Instagram post announcing her engagement, Ivanka commented, “So, so happy for you and Josh! I feel blessed to have you as a sister (!!!) Karlie and look forward to the decades of happy memories we will create together as a family!” Karlie did not respond, and the comment is now deleted. (We’ll get into that in a bit.)

More recently, on the night of the Project Runway season 17 premiere – the first season that Karlie is hosting — Ivanka posted a Twitter video.

“Gosh Karlie, it’s happening!” Ivanka says in a very high-pitched voiced. “Amazing. Project Runway. Karlie is host! [laughs] Epic.”

Karlie did not like or respond to this video. In fact, Karlie doesn’t follow Ivanka back on Twitter.

On Instagram, Ivanka follows Karlie. She continues to likes her posts. Karlie doesn’t follow her back, and hasn’t liked an Ivanka post since December 2015.

Karlie Kloss


Let’s dive into their history, shall we?

MAY 2010: 

Ivanka tweets, “Gorgeous model Karlie Kloss wearing Donna Karan & my rose gold & rock crystal necklace & cocktail ring to the #MetBall”

Karlie Kloss

This was Karlie’s first Met Ball, two years before Karlie and Josh would start dating. Interesting!

JUNE 2012

Karlie starts daring Josh. At this point, Jared and Ivanka have been married for three years, and they have one daughter, Arabella, born July 2011.

Wanna know what their wedding looked like? Here ya go:

(Our favorite part of this is a very concerned-looking Josh Kushner in the bottom left.)

JULY 2012

One month after Karlie and Josh start dating, Karlie likes Ivanka’s Instagram post for the first time. It is a landscape shot of New York City with an ominous cloud hanging overhead.

first like

We don’t know if they’ve met yet at this point, but Karlie had joined Instagram a month prior. (Perhaps because of her new relationship; Josh was an early investor in the social media platform.)


Ivanka will post many, many more times before Karlie likes another post. The next “like” is on a post from September 2013, at which point the amount of likes increase.

Ready for a comprehensive list of what Karlie liked?

• Ivanka’s post of her shoes (Sept 2013)
• The first post of her son (Oct 2013)
• A throwback of Arabella as a baby (Oct 2013)
• A pumpkin carving photo (Oct 2013)
• A picture of Marilyn Monroe (Oct 2013)
• Ivanka posting about her birthday (Oct 2013)
• An image of #TrumpDoral (idk) (Nov 2013)
• A video of Trump Doral (a Trump golf club?) (Nov 2013)
• A video of walking home in the snow (Jan 2014)
• Ivanka with her children (Jan 2014)
A snap of Arabella (Jan 2014)
• Ivanka trying Gwyneth Paltrow’s avocado toast (Jan 2014)
• Ivanka backstage with Vogue (Jan 2014)
• Another snap of Arabella (Feb 2014)
Arabella & Joseph (March 2014)
The cover of Ivanka on Shape Magazine (April 2014)
• Ivanka and Jared posing in front of said Shape cover (April 2014)

At some point, we have to assume, Karlie followed Ivanka on Instagram, and felt comfortable enough commenting and liking her Instagram posts. 2014 was a different time.

MAY 2014

Ivanka and Karlie attend the Met Gala. Ivanka goes with Jared, Josh, and Kevin, Instagram’s founder; she posts an Instagram of the three of them. Guess who likes it? Karlie, duh.

Guess who Karlie went with? Taylor Swift.

Guess who Instagrammed with Taylor? Ivanka.


Ivanka also does a photo diary for People (no photos with Karlie, sadly), where she calls Taylor Swift’s look “flawless,” describing her as “fresh, elegant, and beautiful.”


After the Met Gala, Karlie doesn’t like another Ivanka post until August 2014: an image of pastrami at Second Avenue Deli in New York. Then she likes four more posts: Ivanka and her son, a post of Beyoncé and Nicki Minaj (yes, really, Ivanka posted that), Ivanka and her kids, and a photo of just her kids.

Karlie likes five more Ivanka posts in September, and five more in October, bringing the total up to 32 total likes. Wow! (Note: She does not like this photograph that Josh is in, from Ivanka and Jared’s wedding.) In November, along with two other posts, she likes Ivanka’s post to “go vote.” Ha. In December: three likes. Meanwhile, Ivanka likes Karlie’s posts with some regularity.

Basically, we’re tracking this to show you that the sisters-in-law were seemingly once on good terms. Notably, this was before the Trump campaign and the election, after which public goodwill from Karlie to Ivanka – that could be displayed in things like Instagram likes — disappeared, while Ivanka desperately tries to hang on.

EARLY 2015

To continue our tally of Karlie-liking-Ivanka posts: five in Jan, three in Feb, none in March, and none in April. (Why so selective?! Ivanka also posts like a bajillion times a day.)

One of the posts Karlie likes: when Karlie and Taylor were on the cover of Vogue, and Ivanka was profiled inside. (Ivanka tags Karlie, Taylor, and Vogue in the post.)


On Karlie’s Insta, she clearly does not tag Ivanka, only her BFF Taylor.

(Do you believe in #Kaylor?! LMK.)

APRIL 2015

Ivanka and Karlie both attend the White House Correspondents Dinner, hosted by comedian Cecily Strong.

A month later, Ivanka posts a shot of her and Jared, writing, “Being silly at the #WhiteHouseCorrespondentsDinner 😜 Thanks for snapping this photo @karliekloss#flashbackfriday #whcd

Can we just draw your attention to: thanks for snapping this photo, @karliekloss. Because! Karlie commented!

Ivanka insta

Heart emoji, camera, winky face, thumbs up.

MAY 2015

They both attend the Met Gala again. Karlie doesn’t like any of Ivanka’s Met Gala posts, but double-taps this one of Ivanka at Trump Dubai.

JUNE 2015

Donald Trump announces he’s running for President.

The only Ivanka post Karlie likes in June: this one captioned “Jared and I take turns planning our weekly date nights.”


Two in July: one on Arabella’s 4th birthday, and one of Ivanka and Joseph.

AUGUST: two likes. One is a family vacation shot, and the other is a Taylor Swift quote that Ivanka posts. Obviously.

One like in September (this family photo); none in October; one in November (this Thanksgiving message); and a whopping TWO in December (celebrating Wendi Murdoch and a photo of her kids).


Not a single like. Yes, we went through every single one of Ivanka’s Instagram posts from 2016, and Karlie did not like a single one. This was perhaps when Karlie unfollowed Ivanka (we’re assuming she must’ve followed her at some point to like her posts, as opposed to randomly searching up her boyfriend’s brother’s wife all the time).

This is the year Karlie brings Josh to the Met Gala for the first time. (Again, head to our relationship timeline.)

However, we do know Karlie and Ivanka are still hanging out because…


They attend the U.S. Open together, alongside Jared, David Geffen, Roman Abramovich’s wife Dasha Zhukova, Mike Hess, John Hess, Leon Black, Princess Beatrice (!!), and Wendi Murdoch.

The Daily Mail wrote, “Ivanka Trump watches tennis with Karlie Kloss, a princess and a (Democrat) billionaire.” Here’s an Instagram that’s still live:


It was maybe at this point Karlie realized “liking” Ivanka, and visibly showing fans that they are connected, was a Bad Idea.

See this series of tweets:



You get the idea.


Donald Trump is elected president of the United States.

Karlie voted for Hilary.

What else is there to say?


Again, not a single like by Karlie on any of Ivanka’s posts.


Karlie and Josh attend #MarchForOurLives, the rally for gun reform in Washington D.C. following the Parkland shooting. It’s really the only activist thing the couple has publicly done since Trump has been in office.

JULY 2018

Karlie and Josh get engaged in June; they announce it in July.

The comments are… Not Great. A snippet:

karlie kloss ivanka trump

Meanwhile, Ivanka comments: “So, so happy for you and Josh! I feel blessed to have you as a sister (!!!) Karlie and look forward to the decades of happy memories we will create together as a family!”

Karlie must’ve deleted it, because it’s gone now.


Ivanka is STILL trying. She posts an Instagram story wishing Karlie a happy birthday, sharing the image that Karlie posted on her own feed.



Karlie talks about her political views for the first time seemingly ever in a Vogue profile.

Here are the two paragraphs that get picked up:

The implications of this high-profile union—and her by-default connection to the contentious Trump presidency—are not lost on Kloss. “At the end of the day, I’ve had to make decisions based on my own moral compass—forget what the public says, forget social media,” she says, neither confirming nor denying the conversion rumors. “I’ve chosen to be with the man I love despite the complications. It’s frustrating, to be honest, that the spotlight is always shifted away from my career toward my relationship. I don’t think the same happens in conversations with men.”

Still, the couple has been relatively open about their political leanings. Kushner has been described as a lifelong Democrat, raising hundreds of millions for Oscar, the Obamacare start-up. He also attended the March for Our Lives gun-control demonstration in Washington, D.C., with Kloss earlier this year. “Josh and I share a lot of the same liberal values that guide our lives and the things we stand for,” says Kloss, who Instagrammed about Hillary Clinton—#ImWithHer—during the last election. “We’ve really grown together personally and professionally. Josh knows that I’m just a nerdy, curious human being. I think that’s why he loves me. We have each other’s back.”

It’s worth noting a few things from this:

(1) “Despite the complications,” a.k.a. despite his family’s connection to Trump.

(2) She affirms she shares “liberal values” with Josh.

(3) Although she didn’t confirm it in Vogue, Karlie recently confirmed her conversion to Judaism on Andy Cohen’s show, saying, “I joined the tribe, mazel!” (Andy responds enthusiastically: “You’re a nice Jewish girl! She’s full of contradictions!”

A month later…


Karlie and Josh get married. Ivanka is probably there.

Ivanka posts this Instagram, writing: “So much love for you both as you begin forever together. ❤️” She posted the same thing on Twitter:

Let’s skip ahead to present-day, shall we?

MARCH 2019

Project Runway premieres, starring Karlie Kloss as host.

Guess who wants to get in on her sister-in-law’s rising fame? You know who. She comments on a post of Karlie posing in Times Square with a billboard:

Here’s the comment:

karlie kloss

Karlie does not respond.

And then, Ivanka posts the infamous video of herself congratulating Karlie during the premiere. Many Twitter users have a field day with this video, noting Ivanka’s desperate-seeming attempt to publicize her connection to Karlie (please watch Tavi Gevinson’s parody if you haven’t).


There’s not a single photo of Karlie and Ivanka posing together on the internet — and no, the U.S. Open 2016 paparazzi pictures don’t count. It’s safe to assume Karlie has done everything she can do distance herself, publicly, from her sister-in-law since Trump’s election. Whereas Ivanka is doing everything she can to remind people that she and Karlie are family. Which is awkward. Karlie continues to refuse to acknowledge Ivanka, while Ivanka keeps shouting from the rooftops that they are related.

On social media (where most people are interacting with these two women), Karlie doesn’t follow Ivanka. Although, at one point, she must have, as she interacted with Ivanka’s posts. So: We have every reason to believe that Karlie Kloss unfollowed Ivanka Trump, probably sometime in 2016.

Their IRL friendship may very well still be cordial, if not friendly. They’re married to brothers, after all. But their social media actions speak volumes.

Thank you for your time.

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