Karoline Leavitt Ruined Her Latest Press Briefing Outfit With One Glaring Mistake

Karoline Leavitt was all smiles when she took to the James S. Brady Press Briefing Room in the White House's West Wing on May 9, 2025. She was there to talk about Donald Trump's trade war fallout and ongoing talks to end the Russia-Ukraine war. However, her outfit took center stage. Leavitt looked like she'd rummaged through Hillary Clinton's closet before deciding to plump for a powder blue pantsuit, which wouldn't have been too bad — if it actually fit. However, the big boxy jacket hung off her small frame and looked three sizes too large, while the pants tightly stretched against her legs as she strode in, appearing way too small.

Leavitt has a history of wearing outfits that totally miss the mark, busting out with animal prints and leather on inappropriate occasions, and dressing in skin tight black jeans and stilettos when attending formal events. Oh, and lest we forget! There was the red dress with black trim that she chose to previously address the press about Trump's controversial tariffs in April 2025 — with a focus on China. Kind of unfortunate given the lace trim was actually made in Mabu, China, according to factory workers. "Accusing China is business. Buying China is life. The beautiful lace on the dress was recognized by an employee of a Chinese company as its product," Chinese envoy Zhang Zhishen posted on X, formerly Twitter, along with screenshots from the machinists who created it.

Karoline Leavitt doesn't always make mistakes like that with her choice of clothing. In May 2025, Leavitt showed off her killer abs in skin-baring workout gear. She posted a video of her lifting dumbbells, using the opportunity to spread the gospel according to MAGA. Leavitt said she was done with "woke" brands such as Nike, which caused outrage throughout the conservative world by partnering with Dylan Mulvaney, a female transgender social media influencer, to promote its Alate padded sports bra. (Leavitt added a vomit emoji at the end of her complaint in case anybody was left in doubt as to her true feelings.)

Instead, Leavitt shared that she was thrilled to discover her new favorite workout manufacturers, who "are a pro-America, conservative workout apparel company based in the USA and their clothes are seriously AMAZING!" She continued the Insta promo by decreeing that US citizens should boycott inclusive corporations and "spend our money elsewhere and support businesses that align with our values. That's capitalism, baby!"

However, Leavitt rarely flashes the flesh, preferring instead to often dress more modestly, or some might say, dowdy. Leavitt has aged herself by wearing a frumpy outfit on more than one occasion. It's sparked speculation that maybe Leavitt's trying to bridge the 32-year age gap with her husband by occasionally wearing stuffy old lady outfits. But, whatever the case, girlfriend could do with hiring a stylist STAT.