It’s pretty clear Karoline Leavitt’s personal style leans classic, and we’ll be the first to say she’s sported some cute lewks since becoming Donald Trump’s press secretary. However, there have also been a few occasions when she’s ended up looking more frumpy than fashionable.
We’ll start with the plummy Zara ensemble she picked for her very first news conference. On paper, it was fine, and the color was a bold choice. However, that’s where the positives ended. The particular suit she picked wasn’t particularly flattering for her petite frame (to get an idea of just how short Leavitt is, we refer you to the height difference between her and Lara Trump), and the boxiness ended up drowning her. Had it been more cinched in, that might have helped. Granted, the blazer did have a cinching belt detail at the back, but it was incredibly subtle from the front. Likewise, if the pants had been palazzos, that could have created a longer, less frumpy line.
Another offender to this look? The shoes. While Leavitt actually styled the very same pair of shoes in a more youthful way when she addressed reporters outside the West Wing in early February 2025 (on that particular occasion, she went for an all-black look with diamante detailing both on her jacket collar and on the shoes), pairing them with her already-figure-shortening purple suit only made her look even shorter. Mary Janes can be cute, but because they draw a straight horizontal line across a wearer’s foot, they create the illusion of much shorter legs. On a taller gal (think Kate Middleton), not quite as noticeable. On Leavitt … noticeable. Had she picked a pair of heels without a strap, that would have given the illusion of some height.
Karoline’s camel coat detracted from a potential lewk
Moving on to another bold moment gone wrong, in March 2025, Karoline Leavitt headed off to speak with reporters in a bold pink dress, which she paired with black heels. That, in itself, was pretty chic. In fact, we dare say it gave subtle Elle Woods vibes. However, the camel coat she popped on top made things messy.
To clarify, the coat being camel isn’t the problem here. In fact, done well, the combination of pink, black, and camel could actually make for a very fresh pairing — and because the buttons and belt buckle on her dress were tortoiseshell, there was a touch of cohesiveness in that, too. However, the coat she wore ended up feeling fairly frumpy. The woolly fabric looked a little too cozy for a press briefing, and it almost gave the sense that as she was leaving the house, an elderly relative (or, ahem, her much-older husband) reminded her to take something warm, so she tossed on whatever was closest.
Granted, another style of coat in the same fabric might not have been quite as bad, and even the coat at hand might have worked if she’d gone for a more neutral dress. However, the fact that we were given a dramatic winged collar, a wide notch lapel, pink, and flap collars all in one look is … something. Had the coat been more simple, or even if Leavitt had kept the dress’s collar under the coat itself (a surefire way to make things feel less old-fashioned), we may have felt differently. But she didn’t, so here we are.
Karoline Leavitt’s black and white look was very dowdy
Possibly Karoline Leavitt’s frumpiest look to date was the black and white ensemble she wore for one of her first days on the job. Obviously, we’re referring to the white top, white pants, black coat, black gloves, and black heels look.
We’re not sure where to start, because pretty much every aspect of this outfit missed the mark, but let’s go with the bizarre shoe choice. Despite being completely bundled up on the top half of her body, Leavitt chose to wear a pair of heels rather than boots, which made everything look unbalanced. Then, there was the specific choice of coat (again). This time, it wasn’t the fabric but the actual design that felt frumpy, hitting just above the knee. Leavitt also eschewed the belt, which created another boxy silhouette.
The cherry on top, though (and what made everything feel even more old-fashioned), was Leavitt’s brooch. Fastened to her top, right above the coat’s opening, it almost looked as though she’d worn her necklace above her shirt. No matter how many influencers try to convince us to bring this back, it’s giving less “old money style” and more “old,” period. Of course, we may be wrong, and it may not even be a brooch but rather a feature of Leavitt’s top. Either way, we’re going to say this is one of Leavitt’s worst press briefing outfits yet.
Karoline Leavitt’s pastel blue dress could have been great
Moving on from an outfit with zero redeeming factors to one we really wanted to love, Karoline Leavitt’s pastel blue dress and cardigan combo had a ton of potential … and we’re kind of mad it didn’t live up to it.
In fairness to Leavitt, we’ll start with all the good things. For one, she looked phenomenal in the color. Her choice in shoes was also stellar (read: nude and no more Mary Janes). What’s more, it’s definitely giving Princess of Wales vibes. However, there were a few details that stopped Leavitt’s lewk from being great. Once again, her choice in outerwear created a very boxy look, which in turn made her look shorter, even with the nude heels. As seen in videos from the day, the sleeves on the jacket were also fairly baggy, which added even more boxiness. Had the jacket been cropped slightly higher, that could have been avoided. That said, there were even easier ways around it: Leavitt could have rolled up her cardigan sleeves to take it from mumsy to effortless, or even ditched it altogether (a la Kate Middleton).
Like we said, there’s no question that Leavitt prefers old school chic, and we certainly don’t begrudge her that. However, if it is a Middleton-esque vibe she’s going for, here’s hoping at some point she goes for lines that elongate her figure, rather than drown it.
