Karoline Leavitt's Frumpiest Work Outfits That Didn't Flatter Her

At only 27 years old, Karoline Leavitt is the youngest White House press secretary in the history of the United States. Every day Leavitt gets behind the podium to dodge questions, insult left-leaning publications and news organizations, and repeats the lies and misinformation of the current president. It's a dirty job, but Karoline Leavitt seems to be enjoying herself, as well as her new-found fame.

But like so many of her GOP colleagues, Leavitt has a history of outfits that completely missed the mark, as well as terrifying makeup mistakes that are hard to ignore. In other words, Leavitt, at least in regards to style and fashion, is exactly where she needs to be: in the Trump administration. All one has to do is look at her work outfits. Despite her youthful age, Leavitt chooses to wear some of the frumpiest garments out there. 

While it might be easy to suggest that Leavitt's worst outfits all have one thing in common, her fashion faux pas go beyond one mistake. What's more believable is that Leavitt simply has no idea how to dress herself. Whether it's for work or Easter at the White House with her family, Leavitt's outfits are a master class in how to look as frumpy as possible.

There's so much wrong with this periwinkle dress that it's difficult to know where to start. At first glance, Karoline Leavitt looks like she's trying to channel the pilgrims, that is if the pilgrims had access to blue dye. But on second glance, she looks like a 20-something playing dress-up in her grandmother's clothes. In either case, it's a bad look. So bad that it makes one wonder if Leavitt has a mirror at home.

So many important and powerful women have worn the pussybow blouse and nailed it. Most notably, the pussybow blouse is a garment Kamala Harris rocked during her campaign to send a bold message. But on Leavitt, with this gaudy print to boot, it's just a disaster. If that weren't enough, even Leavitt's shoe choice is bad. Although it's painful to call Chanel frumpy, and may make Coco roll over in her grave, this particular shoe is not for someone under 60.

Here's the thing: monochromatic can be a really winning look. Unless, of course, you're Karoline Leavitt. Here, she's wearing some sort of off-brand twin set paired with a matching ankle-length pleated skirt. Not midi- or tea-length, but pretty much right down to her bland shoes, a trend that's taking MAGA women by storm. Everything about this outfit misses the mark — not that her fellow MAGA buddies are doing much better at avoiding their own take on frumpiness.

When you work for the Trump administration, apparently there are no days off. That's why, on Easter 2025, Karoline Leavitt was fielding questions from reporters in her Sunday best — or was it? If you pay attention to Leavitt's clothes, you'll see a theme. Not only are they frumpy, clearly designed for someone 30 years older or more, but she has a thing for belts and rhinestone buttons. If Leavitt was trying to embrace the worst of the Y2K fashion revival, this look would make sense. However, that's likely not the case. As for the belt, it's just as pointless as the belt Carrie Bradshaw wore around her bare midriff in an episode of "Sex and the City."

In February 2025, Karoline Leavitt was spotted on the White House lawn wearing a dress that was equally gaudy and frumpy, with outdated sleeves and a very questionable hem. In addition to this peculiar getup, Leavitt was carrying an outdated accessory that she can't seem to leave behind: a Neverfull MM tote bag by Louis Vuitton. 

Leavitt is new money by all accounts, so she may not be aware that monogram bags, including those by Louis Vuitton, are outdated. But you'd think she would have opted for another dress before leaving the house. Between the frumpy outfit and the outdated bag, Leavitt is aging herself. But maybe that's the point. If she looks 50-something, then the age gap between herself and her husband won't be so glaring.