President Donald Trump’s new press secretary is still learning the ropes of her job and figuring out her personal work style along the way. Thus far, Karoline Leavitt has worn many outfits that missed the mark for one reason or another: off-putting colors, poor fits, or just plain unflattering. (Once, Leavitt wore an outdated suit with a floral shirt that looked like the upholstery on Grandma’s couch.) But of all her fashion fails, one stands out for its political cringiness rather than its style.

On January 31, 2025 — just days after Trump took office — Leavitt led a White House press conference, during which she discussed the tariffs the president planned to impose on China, Mexico, and Canada to boost the American economy and slow the flow of fentanyl into the U.S. Unfortunately, she chose an outfit that was wrong for the occasion on several counts. Her bright red sweater dress wasn’t quite businesslike enough for the occasion, not to mention being a bit stuffy for a Gen Z staffer. The most problematic issue, though, was the manufacturing. Zhang Zhisheng, the Chinese ambassador to Indonesia, put up a comment on X (formerly Twitter) pointing out that the dress appeared to have been made in China. Zhang added a biting comment essentially saying: “Complain about China’s business practices all you like, but hey — you’re still buying our products.” It was an embarrassing “gotcha” that even Leavitt is probably cringing about now.

Karoline Leavitt Needs To Watch Her Messaging

Karoline Leavitt in red sweater dress stepping onto White House platformMost of us don’t dress with a particular agenda in mind, but public figures have to be keenly aware of the messages they send with their clothing. For instance, First Lady Melania Trump has worn outfits that mean more than you might realize, such as the no-nonsense pantsuit she wore for her first official portrait in President Trump’s second administration. (We’ll hold off for now on discussing that infamous “I Really Don’t Care, Do U?” jacket.) Karoline Leavitt has now learned it’s not a great idea to wear a “Made in China” product when your boss is trying to convince the world that mean ol’ China needs to be punished with tariffs which will raise the prices on dresses like hers. Granted, some on X are claiming Leavitt’s dress was actually American-made, but a rookie cabinet member can’t afford to make such easily avoidable slip-ups.

With time and perhaps some coaching from a fashion advisor, Karoline Leavitt can refine her personal style and perhaps convey an important personal or political message in an intentional way. She could even take inspiration from another fashion-forward first lady. Michelle Obama’s bold 2024 Democratic National Convention outfit sent a strong message to former haters. As she sang the praises of candidate Kamala Harris, she wore a sleeveless suit.

It was a pointed “f-you” to everyone who once criticized her sleeveless dresses as being too skin-baring and unprofessional for a president’s wife. Maybe Leavitt will never be able to wear a typical Gen Z hoodie-and-flare-jeans ensemble to an official press briefing, but hopefully by the 2028 elections, she’ll have found a look that looks both businesslike and youthful.