Karoline Leavitt has a habit of showing up to work in frumpy outfits that don’t do much to highlight her figure, but every so often, she turns heads with a surprisingly daring ensemble. During a press event in March 2025, for example, Leavitt swapped her standard boxy suit for a black fitted top and sexy pleather pants — giving Elon Musk something to look at. While trailing behind Leavitt and President Donald Trump up the steps of Air Force One, Musk was caught stealing a glance at Leavitt’s backside before quickly catching himself and looking away. Footage of the awkward moment made its way to Diario AS’s YouTube channel, where it racked up dozens of reactions and over a million views.

Most users sided with Musk, saying the Tesla and SpaceX CEO was acting respectfully and handled it better than most would have. “What is awkward about this? It was a windy afternoon and they’re both just walking to the plane,” one said. Others questioned why Leavitt would wear those pants in the first place: “Your title was fine. Yes he was trying to avoid. But I’m wondering why she would wear that.” Some even suggested that she opted for the skin-tight look knowing all eyes would be on her. “You don’t wear those pants and be worried about someone looking at you,” another user stressed. Leavitt even posted a snap of her look on Instagram, where critics continued to mock her outfit choice. “Where was your tacky polyester outfit made?” one user asked the press secretary.

Speaking of inappropriate, Karoline Leavitt is also guilty of flaunting a little too much leg in the workplace since becoming the youngest White House press secretary. In April 2025, she uploaded a photo with President Donald Trump on the White House lawn ahead of a scheduled press briefing. Leavitt sported a modest-looking dress that hit just above the knee, dressing it up with a beige cardigan sweater and heels. There was also that time when Leavitt donned a press briefing outfit in a tasteless mini-dress that showed just a little too much skin. And she did it again in June 2025, rocking a dress inspired by first lady Melania Trump that gave viewers an eyeful and her critics plenty of ammunition (seen above).

However, when she’s not showcasing her figure or flashing a little leg, Leavitt likes to play it safe with her wardrobe. Only, she occasionally misses the mark by choosing the wrong fabrics and/or silhouettes; even her hair and makeup fall flat at times. Oriona Robb, a fashion stylist, told The Mirror US in 2025: “There has been criticism that she can look almost too polished and veers towards the ‘Stepford Wife’ image, with the perfect woman appearance and not a hair out of place. … Her style is very put together and considered, which can at times feel odd given her age as she’s only 27.” 

Her advice for Leavitt? Trust her instincts. “Ultimately, if this is what makes her feel the best in her role and to be her best self in a career that is constantly in the media, she should be able to choose what she wants to wear and to have a wardrobe that makes her feel empowered and confident,” she said of the press secretary.