Donald Trump’s press secretary, Karoline Leavitt, has continually missed the mark with outfits that have aged her well beyond her years. On March 27, she took to her Instagram Stories to promote the Podcast Row event at the White House. “Our team has gathered a room full of podcasters with cabinet officials [and] White House officials,” she said in a short clip. The baby blue ensemble that Leavitt decided to wear for the occasion distracted from her remarks about the event. She sported a loose-fitting full-length dress with a high collar and full sleeves. Somewhat surprisingly, Leavitt completed the old-timey look with a pair of black high heels, which seemed thematically mismatched with her outfit. The baggy blue dress concealed Leavitt’s figure and brought back memories of the old-fashioned high-collared flannel nightgown pajamas that were repopularized in the ’80s.

Leavitt earns a hefty salary as Trump’s press secretary, and she does use some of that money to buy stylish outfits that do not look straight out of the 1800s. After posting the video in the pajama-like blue dress to her Instagram Stories, Leavitt added an older snap of her wearing a chic dark green pantsuit.

Despite possessing the ability to look fashionable, Leavitt has often opted for an overly conservative aesthetic. Days before donning her frumpy nightgown look, Leavitt wore an old-timey outfit in photos she posted to Instagram to celebrate passing one million followers. She had on a lilac blue sweater and a full-length pleated skirt combo that got trashed in the comments. “Fire your stylist. You’re 27yo. This outfit is giving Nana having brunch at the club,” one Instagram user wrote. Of course, that was not the only outfit that led to Leavitt being roasted.

Those unflattering looks came just a couple of weeks after Karoline Leavitt wore a grandma-style outfit to a press briefing at the White House on March 11. It was a tweed mint green dress with short sleeves and a high collar. The old-fashioned outfit had silver adornments lining the pockets, front closure, and collar. It was so bad that it had us wishing Leavitt would take a page out of Kimberly Guilfoyle’s style playbook and spice it up a little. 

Days after, Leavitt wore a more modern outfit while addressing the press outside the White House. On March 15, she uploaded two photos to Instagram of her rocking a pink dress with buttons up the front and a belt around the waist. Leavitt wore a brown wool trench coat over the dress as she spoke outside. Even though this was a more fashionable look than her ’50s aesthetic, she was still roasted in the comment section. “It’s wildly impressive that you can make a 27 year old look 40,” one commenter replied. 

Whether Leavitt completely conceals her figure or wears something more revealing, there seems to be no satisfying the trolls. Prior to becoming the White House Press secretary, she posted an Instagram carousel from a trip to Nantucket Island in July 2023. The lead image was a spicy shot of her posing in a skintight athleisure wear romper. That low-cut number put her assets on display and was derided by those who prefer the loose-fitting apparel Leavitt opts for during pressers. “It’s not very ‘conservative’ to have your boobs hanging out,” one troll commented in March, well after the post was originally published.