Karoline Leavitt Wore Some Seriously Bad Outfits In 2025

2025 was a major year for Karoline Leavitt as she became the youngest White House press secretary in history. She also settled into married life after finally tying the knot with her much-older fiancé, Nicolas Riccio, to whom she became engaged in 2023. (The pair, who share a 32-year age gap, are parents to one son, Niko.) But fashion-wise, it was also a year of sartorial faux pas and questionable taste for Leavitt; the Gen Z conservative tends to age herself with frumpy outfits and has a bad habit of choosing silhouettes that do absolutely nothing for her figure. Granted, she's aiming for professional and put-together, but dressing for the part surely doesn't have to be this ... boring? Right? Especially since her throwback pics suggest she's capable of pulling off head-turning lewks, so perhaps it's time she brought some of that energy back to her current wardrobe. Just saying! 

Anyway, all of this is to say, Leavitt wore some seriously bad outfits in 2025, some of which we can't get out of our heads (like her oversized green blazer at a press gaggle in June — what was that?!) and could write a whole article about. Below, a roundup of her most questionable, confusing, and downright cringe-worthy looks of the year. Here's hoping 2026 is a better year of style for the press secretary.

Did somebody say hot mess express? We can't help but wonder what exactly was going through Karoline Leavitt's head when she chose this particular dress to wear to a press briefing. Between the fabric, the style, the messy curls, and her choice of footwear, everything about this ensemble just felt off. All it needed was a scarf around her neck, and she'd look like the lead of a Hallmark Christmas movie. Perhaps swapping those boots for black pumps would have made this outfit more professional and slightly less chaotic? Hmm. We have a lot of thoughts for this look, but unfortunately, none of them are positive.

Karoline Leavitt tried to bridge the age gap with her husband, Nicholas Riccio, in her stuffy old lady outfit while catching up with Donald Trump. In April, she shared this photo of herself and the president walking outside the Oval Office of the White House ahead of a scheduled press briefing. Fans would be forgiven for thinking that Leavitt was older than 27 here; she wore a tweed plaid dress with a beige cardigan and nude pointed-toe heels that overall screamed grandmacore. The dress itself was already bland enough on its own, but the addition of her sweater pushed it into dowdy territory with its muted tone that also washed Leavitt out completely. Whatever happened to a pop of color? Sigh.

Oof. This one was just hideous. In June, Karoline Leavitt spoke to a gaggle of reporters outside the West Wing of the White House in a green, dare we say, fugly, oversized blazer that looked ripped from her husband's closet. Look, we understand she took a big risk here, okay? And sometimes you win, sometimes you learn. The press secretary styled her frumpy jacket with black trousers and a pair of black-and-white heels, but the whole look just came off as sloppy. Especially with this shade of green — just tacky! Oh, well.

The upper half of this knit dress is good, the mini-skirt, though, is not. (What is with Karoline Leavitt and knits, by the way?) Of all the leggy looks she's donned since becoming press secretary, the Trump comms aide completely missed the mark in this navy blue frock by Self-Portrait that screamed Forever 21. Even for 27, this lewk felt a bit too trendy and juvenile (not to mention tacky!). Is it cute? Sure. Is it White House-appropriate? Not even close! Perhaps she should ask herself that more when choosing her next outfit. 

Has Karoline Leavitt ever heard the saying, "You should wear the dress; the dress shouldn't wear you"? 'Cause it seemed to us that she didn't get that memo. Here, she was photographed wearing a blue belted dress with a modest neckline and a loose fit, looking as though she was cosplaying a 1950s librarian or a stern headmistress. Honestly, she could've made it work with just a few undone buttons and some statement accessories, or rather, by simply tightening the belt to give her dress some structure and create a more flattering silhouette. The bedhead certainly didn't do her any favors, either. All in all, not her finest moment.

Mixing black with navy blue is always a tricky business — one that Karoline Leavitt failed spectacularly in when she dressed up for a 9/11 memorial service at the Pentagon in Arlington, Virginia. Here, she paired her Self-Portrait cropped cardigan with a black pleated skirt and oversized sunglasses with thick frames, keeping her makeup minimal and her hair sleek and wrapped in a bun. We hate to break it to you, Karoline, but Melania Trump's signature accessory just doesn't work for you. And you might want to rethink that cardigan situation.

Time for a break! Karoline Leavitt joined President Donald Trump at the U.S. Open men's final match between Jannik Sinner and Carlos Alcaraz in New York City's Arthur Ashe Stadium. Seen here with Margo Martin, the White House press secretary sported a white jumpsuit with a boxy top and high-waisted pants that didn't quite flatter her figure. The proportions were off, and she looked especially frumpy next to Martin, who was a head-turner in her black polka dot dress by Et Ochs. We appreciate the effort, but she should've followed Martin's lead and opted for a cute flowy frock instead of — whatever that is. Next!