Throwback Pic Of Karoline Leavitt's Attempt At A Blowout Couldn't Be More Of A Mess

White House Press Secretary Karoline Leavitt is almost as well-known for her connection to President Donald Trump as she is for sporting several outfits we hope Leavitt never wears again. The White House staffer has also shown a poor track record concerning her makeup routine which, sadly for Leavitt, can be pretty cakey. Her hair apparently isn't immune to the press secretary's poor style and cosmetic judgement either, and she especially dropped the ball on a holiday that Leavitt should have been on her A-game for.

Thanksgiving is a time for families to dress up in nice, comfortable clothes and gather together for a wholesome meal. Such was the case for Leavitt and her baby son, who were all gussied up in a photo she posted on Instagram to celebrate the holiday in 2024. Though she was obviously living it up in the moment, the special occasion might have been ruined for others after noticing the awful blowout that partially obscured her flashy Christmas wreath. Contrary to how others typically pull off the hairstyle, Leavitt's rendition lacked any volume or smoothness. Her hair instead was split into several jagged clumps, which fractured off in different directions without any real rhyme or reason.

Karoline Leavitt's broken blowout was undoubtedly the biggest blunder of her matronly getup, but the Trump staffer's frilled button-up dress wasn't any reason for her to give thanks either. The flesh-colored number mixed soft, textured material with black strips running around the neck and cuffs and down the middle with gold buttons, alongside a strangely flounced hem. Though we'll concede the outfit at least looked cozy enough to fit the near-winter occasion, we couldn't help but notice that the sweater-coded dress looked rather old-fashioned for someone Leavitt's age. 

The look comes as no surprise, however, as the youngest press secretary in history is a regular culprit of dressing in styles which make Leavitt look way older than she really is. Instagram commenters thought the same, voicing their disbelief at her young age. "How are you 27?" one asked. "You look 45." Though she might take such mature comparisons as a compliment, others could argue the outfit makes Leavitt look elderly from the neck down. 

On the bright side, though, just as with other dodgy ensembles, like the black tweed dress she donned in April 2025, which made Leavitt look like she was ready for an early bird dinner with her decades-older husband, her Thanksgiving look also could have helped diminish any questions about Leavitt's age gap relationship with Nicholas "Nick" Riccio.