Karoline Leavitt's Failed Attempt To Keep It Casual Proves Her Trump Obsession Won't Quit The List
Press Secretary Karoline Leavitt continues her worship of Donald Trump even when she's relaxing, as evidenced by the photo of White House staffers.
By May 16, 2025 9:00 pm EST
Petite Press Secretary Karoline Leavitt seems to enjoy her job so much, she simply can't take a day off. Or, rather, when she does take a day off, she's sure to remind everyone that her allegiance lies with President Donald Trump, both on and off the clock. For example, there was the time Leavitt posted a photo of her playing the role of working mother; however, upon further reflection, it revealed she keeps photos of Trump lying around her workspace. To make matters worse, there was the time Leavitt upped her glam game, possibly in an attempt to get Trump's attention. While these may seem like harmless instances, three times does make a trend â and Leavitt has once again dazzled with a Trump-inspired outfit.
Will Scharf, assistant to the president and White House staff secretary, shared a group photo in an Instagram post of several members of various communication departments posing together in front of Air Force One. Some are looking a bit more dressed-down and casual than usual, indicating this was a day off treat. However, not only is Leavitt once again wearing some grandma-inspired sneakers, but her sweater is giving her away as well. What looks like an innocuous American flag actually appears to have the name "Trump" spelled out beneath it, indicating that even during her downtime, Leavitt can't quit her Trump-inspired grandma chic sensibilities.
Wearing an American flag sweater with the name "Trump" emblazoned across the front is just one in a growing list of examples of how Karoline Leavitt's MAGA makeover is doing her dirty. As she nestles into her position as White House press secretary, Leavitt has found herself often opting for a sense of fashion that doesn't suit her. In a bad habit, Leavitt consistently dresses older than she really is, making it hard to remember that she's still in her 20s â a feat she could be celebrating instead of running away from it.Â
There's also the troubling trend of outfits she most likely found in her grandma's closet. For example, the time Leavitt channeled her inner babushka and wore a scarf fit for an elder, or even the bizarre fringed nightmare of a jacket Leavitt wore. As much as she might be trying to embody her rather prestigious role within President Donald Trump's administration, too much can simply be too much. Between her outdated sense of conservative fashion and strange fawning over Trump, Leavitt might need a vacation from the circus â one where she leaves all her Trump memorabilia at home.