Karoline Leavitt has a bad habit of aging herself by wearing frumpy outfits, but the White House press secretary’s only wardrobe issue isn’t her odd attachment to dowdy duds that actually has us begging her to take some style advice from Kimberly Guilfoyle and ditch the granny garb. Sometimes, Leavitt struggles to put together looks that are event-appropriate. Other times, she dresses not to impress — but to offend.
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Back in 2023, Leavitt set the tone for her future role in Donald Trump’s administration by trying to troll the left with one of her style choices. At the time, she was a failed congressional candidate who had learned the art of deriding Dems from former White House press secretary Kayleigh McEnany. If Leavitt seems like a McEnany wannabe, it might be because she served as an assistant press secretary to McEnany during Trump’s first term. But Leavitt wasn’t quite dressing for the job she wanted in an Instagram post that included a photo of her wearing a black tank top, Daisy Dukes, and a black snapback. Her look was far too casual for the briefing room, and her goal wasn’t to defend her party’s policies or tout Trump’s perceived victories; it was to make the superficial statement that “Republicans are hotter.”
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The pink lettering on her hat included a promo for a conservative dating app, but because Leavitt had already found love with her much-older husband in the real world, she didn’t need it herself. Still, one snarky response to her post read, “Is this where 30 yr olds meet 60+ yr olds?” And, of course, her divisive message sparked a debate over the accuracy of her claim. At least some of her other questionable apparel choices weren’t such blatant attempts to get under people’s skin.
Karoline Leavitt clung to her teen years with a Clueless clothing choice
When Karoline Leavitt got dressed for the September 2024 presidential debate, perhaps she had another debate in mind: Cher Horowitz’s pro-refugee argument in the movie “Clueless.” Leavitt’s plaid miniskirt and blazer combo looked like a less luxe take on the teen’s iconic yellow ‘fit. The vibe was all wrong for the event, and considering her boss’s view on immigration, Leavitt would probably scoff at Cher’s argument “that it does not say ‘RSVP’ on the Statue of Liberty.” But hey, at least there’s no semi-incestuous stepbrother dating in this episode of “The White POTUS.”
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She channeled chewing gum in a tasteless zebra-print dress
Can you smell the artificial fruit flavor emanating from the body-con dress Karoline Leavitt wore during a 2023 visit to Mar-a-Lago? Her green zebra-print number wasn’t just tasteless; it resembled a green piece of Fruit Stripe gum, which was notorious for becoming flavorless as soon as you popped it in your mouth. Her garb also looked particularly garish when surrounded by the gaudy gold décor of Donald Trump’s beach club. Somehow, Leavitt thought the dress was work-appropriate, as she captioned a photo of it, “Here for business and pleasure.”
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She addressed the press while dressed like Paris Hilton
Karoline Leavitt owns several pieces from Self-Portrait. She’s been deemed a “hypocrite” online because Donald Trump is desperate to get Americans to spend their money on their own soil, and Self-Portrait is a U.K.-based label with factories in China. One of the brand’s designs in Leavitt’s closet is the crystal-embellished mint green minidress she wore for a 2025 press briefing. It was granny brunching up top and socialite party girl on the bottom. In fact, the same twee tweed outfit was worn by Paris Hilton in a more appropriate setting: while filming her reality show “Paris & Nicole: The Encore.”
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Karoline Leavitt’s look that was too hot for a pandemic-era holiday party
She’s not bad; she just dresses that way! To be fair, when Karoline Leavitt channeled Jessica Rabbit at the 2020 White House Christmas party, her glittery red dress was fittingly festive and undeniably sexy. However, her sex appeal probably should have been the last thing on her mind amid a global pandemic. The event also presented her with a golden opportunity to demonstrate her dedication to putting the “Christ” back in Christmas, but curiously, Leavitt’s signature pricey cross necklace wasn’t hovering above her exposed bronzed cleavage.
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Her distressed denim held on for dear life at a soccer match
Thankfully, Karoline Leavitt didn’t have to put together outfits before taking the field for her college softball games. Unfortunately, she didn’t have a uniform when she attended a 2018 soccer match. From the waist up, she was fine; she wore a T-shirt demonstrating her allegiance to Italy’s AS Roma football club. However, her distressed jeans were a disaster. A humongous hole in one thigh crept dangerously close to her bikini line, and the soccer fan’s “goal” seemed to be to show off as much thigh as possible without turning her jeans into cutoffs.
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Karoline Leavitt won’t be tardy to the Leopards Eating People’s Faces Party
For CPAC 2025, Karoline Leavitt dressed like a Real Housewife attending a promotional event for her line of jewelry, bikinis, fragrances, alcoholic beverages, sex toys, etc. There was a whole lotta leopard print covering her knee-high black boots, but it’s a pattern high-profile Republican women should probably try to avoid. You see, there’s a famous tweet that reads, “I never thought leopards would eat MY face,’ sobs woman who voted for the Leopards Eating People’s Faces Party.” And, unfortunately for Leavitt, this form of oblivious buyer’s remorse is often associated with Republicans.
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Karoline Leavitt’s vision for America’s future involves a lot of bleach
If Karoline Leavitt gets her wish, America will someday look like the endgame of “Village of the Damned.” She caused such an uproar by wearing a “Make America Blonde Again” tee in a selfie that Snopes had to verify that the photo was authentic. One tweet summed up the sentiments of many of Leavitt’s critics: “The whole thing stinks of white supremacy.” Maybe she was dropping a hint that the key to surviving the Trump economy is to invest in lots of (American-made) bleach.
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