Karoline Leavitt's Questionable T-Shirt Will Always Haunt Her

From Karoline Leavitt's ensembles that are making her look so much older, to her outfits that have been downright inappropriate, she can't seem to get this glam thing down. Luckily for her makeup stylist, Karoline Leavitt is stunning without makeup. But even when she gravitates towards less-risky sartorial choices, like the world of graphic tees, it doesn't end up working in her favor.

Leavitt was 27 years old when she was hired as the White House press secretary, making her the youngest in American history. A lot of pressure sits on Leavitt's shoulders to stay up-to-date with trends, but where fashion is concerned, all she does is backslide. Before she got the job in January 2025, Leavitt took a selfie in a hair salon wearing a "Make American Blonde Again" T-shirt. Leavitt never posted the pic to social media, but an X user uploaded it to the platform in March 2024, later receiving authentication from the White House in March 2025.

During Donald Trump's years of campaigning, "Make America Great Again" became his slogan, and he soon plastered it on anything he could sell. The slogan, being aligned with conservative ideals, along with the quip for everyone to become blond, reminded many of the Aryan ideals Adolf Hitler attempted to implement during the Holocaust. One wrote on X, "Hints of 1930's Germany...." Another expressed, "And the race of blonds is ..... That is what they are actually standing for."

Whether it's a shirt as obvious as the "Make America Blonde Again" tee, which she reportedly bought from her hairdresser and wore while she was in the salon, or a less blunt choice, Karoline Leavitt can't seem to stay away from political pieces. That's particularly true when it comes to graphics on all forms of clothing.

In June 2023, she posted a picture to Instagram wearing a trucker hat that read "Republicans are Hotter." In the caption, she said that the hat was given to her by Date Right Stuff, writing that it was "the anti-woke dating app for conservatives. Only 2 genders allowed!" This is problematic for a multitude of reasons, and users did not hold back when providing their two cents in the comments. One user wrote, "Is this where 30 yr olds meet 60+ yr olds?" in reference to the major red flag in Karoline Leavitt's marriage with her husband, Nicholas Riccio, who is 32 years her senior. Another user added, "Ewwwwwwww." Maybe Leavitt should stick to the grandma looks, after all.

As mentioned previously, Karoline Leavitt's varying styles have all but given us whiplash. From drab, buttoned-up outfits to questionable tees like her "Make America Blonde Again" shirt, to her looks that showed a bit too much skin, Leavitt can't seem to find a happy medium. At least Karoline Leavitt is now on her way to embracing the "Mar-A-Lago face" trend. But Leavitt's questionable fashion choices leave us with one question: Why is her sense of style so all over the place?

There isn't an exact answer, as Leavitt isn't exactly a fashion mogul. However, her more formal attire that she wears to press briefings and public events, like her famous powder-blue look, is likely an attempt to make her seem more mature and qualified for her position, as her age has been a massive roadblock for her credibility.

As for the aforementioned graphic tee and hat, while one was from a sponsored ad, it likely represents what Leavitt wears when she's not on the clock, as they both came before she joined the Trump administration. As for her more risqué looks, like her Celtics game look from May 2023, it's important to remember that Leavitt is still a young adult in her 20s, attempting to figure out her style, just like the rest of us.