Karoline Leavitt Outfits That Totally Missed The Mark

Although Karoline Leavitt may seem new on a national level now that she's Trump's press secretary, she's been in politics for quite a while. Born and raised in New Hampshire, Leavitt first tried her hand at a congressional bid in the First District in New Hampshire in 2022 against Democrat Chris Pappas in which she got 45.9% of the votes compared to Pappas' 54.1%. While that's decently close, especially for someone new running against an incumbent, the campaign left Leavitt more than $100k in debt, an amount that she still hadn't settled in the summer of 2024.

Somehow, that hasn't impacted her shopping, as she reportedly wore a $900 cashmere outfit to a January 2025 press briefing, rivaling some of Ivanka Trump's expensive outfits. The 27-year-old press secretary seems aware that people are paying attention to her looks, though, as she made headlines for wearing a cross necklace. Yet despite her money and age, Karoline Leavitt has been unable to break the curse of repeated bad fashion choices that seems to plague those in the Trump administration. Along with Leavitt's slew of makeup mistakes that have been hard to ignore, she has worn some outfits that should have gone through a stylist. 

Karoline Leavitt is certainly not the first person to wear the pussy-bow blouse and she definitely won't be the last, but considering the history of the blouse, it's not just a strange choice for her, but completely inappropriate. This is especially the case given the fact that in this photo of Leavitt, she was in Manchester, New Hampshire campaigning for Trump in May 2023. Also called a "the lavallière," the pussy-bow blouse came into fashion in 19th century France and was often worn as a sign of resistance, as more women entered the workplace, as well as a garment mostly worn by artists, intellectuals, and people who politically aligned themselves with the left. It was a staple in Kamala Harris' campaign outfits for a reason. It has also been suggested that when Melania Trump wore the pussy-bow in 2016, shortly after Trump's infamous Access Hollywood tape was aired, she was making a statement by wearing it.

In 2018, when Sara Danius, secretary of the Swedish Academy, was pushed out of her position, the pussy-bow became even more political. "[Danius'] signature blouse went viral... The garment (became) a feminist symbol," gender studies professor Jenny Sundén told CNN. "People even took it to the streets, this pussy-bow blouse manifestation outside the Stock Exchange building in Stockholm, where the Academy convened." If Leavitt knew these things and the intricate history behind the seemingly innocent blouse, she probably wouldn't be caught dead in one ever again.

In 2020, Karoline Leavitt chose to wear this little number to the White House Christmas party. While it's not a bad or even ugly dress, per se, it's the person who's wearing it that make it problematic. 2020 was the year of COVID-19. Not only did the world shut down for months to try to get control of the epidemic, but the World Health Organization now puts the death toll from COVID-19 at more than three million in 2020 alone, a figure that has only come to light in the last few years. However, despite the worldwide tragedy unfolding all around her, here's Leavitt — without a mask, mind you — rocking a sparkling dress at a holiday party. 

In case you blocked it out because you don't want to remember the horrors of it all, holiday season 2020 was unlike any other. People were forced to stay put and not travel to see loved ones, for fear of the health risks they might be taking for themselves or those around them that might be extra vulnerable to COVID. But clearly this wasn't a concern for Leavitt or anyone else at the holiday party. Instead, these people basically gave a middle finger to the restrictions at the time, putting everyone they came in contact with in jeopardy of contracting COVID. 

Although Karoline Leavitt may only be 27, that doesn't mean she can't show some level of professionalism when she attends work-related events — and this absolutely isn't it. In September 2024, Leavitt attended the presidential debate dressed like she was about to pledge a sorority in 2005 instead be a representative of Trump, which she was at the time.

The pink and beige plaid suit comes across as a bad Chanel knockoff — and knocking off Chanel is never acceptable — but it just reeks of someone who clearly has no idea how to dress for the year or the event she's attending. Granted, the Trump family has a love for outdated trends and the entire administration isn't known for their sense of fashion. But one would think that because Leavitt does have youth on her side, she'd be a bit more in-the-know of current styles. Between the Pepto-pink shirt, plaid suit, and a skirt that's a bit too short for such an event, it's hard to take Leavitt seriously — not that it's easy to take her seriously as press secretary either considering her approach.

Not to compare Karoline Leavitt to someone who campaigned for Kamala Harris in the fall of 2024, but there's a very good chance that anyone who was out there representing Harris was not showing up to rallies in a pleather dress. But yet here's Leavitt having a grand old time at Trump's Madison Square Garden rally in October 2024 wearing a pleather concoction that looks like it's supposed to made of alligator or a similar type of animal.

"This is an iconic moment for our campaign," Leavitt told Fox News that night. "President Trump is iconic. Madison Square Garden is iconic. It's his home city, he helped build the skyline of this city and this really marks the closing pitch for our campaign."

In the photo, Leavitt poses with campaign colleague Sonny Joy Nelson who seemed to miss the memo on flouncy sleeves being out-of-style. However, Nelson did nail the color theme by choosing to wear teal as if she, like Serena Joy Waterford, is married to a commander of Gilead. This is also a color that Ivanka Trump has sported during one of the many times that her outfits totally missed the mark.

Let's be honest: the mob wife aesthetic is fun. A lot of fun. Big hair, lots of makeup, long talon-length nails, the perfect amount of gaudiness, and with an attitude that can be both shrill and terrifying, it's no wonder that here we are in 2025 and celebs are proving the mob wife aesthetic isn't going anywhere. One of the most essential components of this particular aesthetic is the leopard print. It's also a print that Karoline Leavitt thought appropriate to wear to the 2025 CPAC on February 2021, because of course she did. To make matters even worse, she paired the dress with the black knee-high boots — great for a night on the town, but not a political event.

On the day that Leavitt wore this outfit, she did an interview with Mercedes Schlapp in which she spoke about all the women in the Trump administration and how much Trump believes in and listens to women. At another point, Leavitt sat down with Megyn Kelly, who not only has worn several things that have fallen flat herself, but has defended blackface in 2018, which led to her losing her job. Although Leavitt didn't praise Trump in this particular interview and his respect for women — her words; not ours — she did talk about her congressional run quite a bit. You know, the one she ran with Trump-style corruption and for which her debt still lingers.