Karoline Leavitt Outfits That Totally Missed The Mark In 2025

Although it's unlikely anyone in the Trump Administration will be winning any fashion-related awards this year — or ever, for that matter — when it comes to consistently missing the mark with her outfits, you can always count on Karoline Leavitt to take the crown. While she may not be the worst dressed in the White House, as that honor goes to Pam Bondi and her penchant for outdated trends, Leavitt isn't too far behind. Whether she's showing up to her job as the youngest press secretary or out and about with her family, in 2025, Leavitt's outfits always have an element about them that feels off. If her ensembles weren't painful enough on the senses, Leavitt's go-to accessories are also woefully outdated.

What's most interesting about Leavitt's outfits is that she has professional assistance in the style department. She works with a Boston-based pharmaceutical consultant-turned-fashion-designer, Christopher Cuozzo for some of her looks. Cuozzo, who never studied fashion, having a degree in political science instead, told WWD in May 2025 of Leavitt, "I think she's very well-dressed whether she's in my garments or someone else's. She presents herself very well." One look at Cuozzo's Instagram and it's understandable why this is his opinion on the matter. In other words, he's definitely no Tom Ford.

As 2025 comes to a close, we thought it would be a good time to look back at Leavitt's outfits from the past year that missed the mark. While some are far more egregious than others, consider every one a lesson in what not to wear.

While Karoline Leavitt has many frumpy work outfits that don't flatter her, this periwinkle dress that looks more like a belted bag, is at the top of the list. Why anyone under the age of 60, who isn't involved in a religious organization that demands women dress like this, would want to wear this outfit, is truly baffling. Not only is it ill-fitting, too conservative, and not doing Leavitt any favors, but it doesn't even constitute being proper work attire. Unless, of course, one were an elderly schoolmarm. Then, and only then, would this make sense for the workplace.

As we saw in 2025, menswear outfits were everywhere, and no one could get enough of the oversized blazer trend. But when Karoline Leavitt tried her hand at this comfy yet chic look in June, she missed the mark entirely. In fact, Leavitt's attempt at playing with proportions was such a fashion fail that it was literally stunning to witness. Not only was the blazer cartoonishly large, but the lime green color clashed with her complexion. As for the black pants, they should have been tighter in order to nail the trend. Instead, Leavitt looked like she was being swallowed by the outfit.

While she wears a lot of questionable articles of clothing, Leavitt's worst outfits all have one thing in common: she's dressing for her husband's age bracket. Leavitt, who turned 28 in August, is married to real estate developer, Nicholas Riccio, who turned 60 earlier this year. The pair have a whopping 32-year-age difference between them. Because of this, when Leavitt pulls out a pink sweater that looks like it was crocheted by her grandma and is embellished with tacky silver buttons, it's easy to understand why: she's dressing for boomers.

As if one homely sweater wasn't enough, Karoline Leavitt showed up to work in a purple twin-set that looked almost identical to the pink one. Again, this was a frumpy, unflattering choice for a Gen Z public figure. To make the outfit even worse, she paired it with high-waisted khaki pants that fit more like mom jeans than the way flat-front trousers should fit. Although one could argue dressing fashion-forward isn't a requirement to be press secretary, as evidenced by her onslaught of cringe-worthy ensembles, everything about this looks cheap and suggests a disconnect with the times.

Considering the fact that Karoline Leavitt has rocked leggy looks, even to work, when she does a 180 and wears something so ultra-conservative like this, it further proves that she struggles to maintain a sense of cohesive style. While at a glance, there was nothing particularly wrong with this outfit, especially if she were headed to church, it was an odd choice for a day at work.  The matching knit fabric on the dress and cardigan made matters even worse because it cheapened the look's overall appearance.

As Karoline Leavitt proved earlier in 2025, playing with proportions doesn't work for her at all. However, that didn't stop her from trying again in October. Again, the shirt was too oversized, especially in length. The pants were also too baggy, especially when paired with the extra large top. While one could make the case that the pinstripes were a cute choice and far more fitting for Leavitt's age demographic, the disconnect between the sizing made the outfit look mismatched — apparently, Leavitt didn't learn from proportion-playing fail 1.0.

Just when you think Karoline Leavitt can't get any more conservative, she pulls out one of her leggy looks. While a more flattering choice for her age and her shape, the glitzy thread woven into the fabric isn't professional at all. Because shimmery thread on a work outfit isn't enough, this dress is also covered in shiny buttons that serve no purpose and only exist as embellishments. In fact, the only thing even remotely professional is the bland shoe trend that took MAGA women by storm in 2025. Everything else makes Leavitt looks like it's her first day on the job and she hasn't figured out what's appropriate to wear and what's not.

What does Karoline Leavitt and a 10-year-old have in common? A love of tacky embellishments, like rhinestones and fake pearls. To add to those details, this dress even has capped sleeves with basting stitching to give them some low-key puffing. Again, this is not a professional look for anyone and it's also severely lacking in sophistication, something that can make Leavitt difficult to take seriously. Considering how Leavitt chooses to talk to some of the journalists during press briefings, you'd think she'd opt for something less juvenile. After all, no one wants to be demeaned by a Gen Zer wearing this.

While the mob wife aesthetic was still sticking around in early 2025, there's also a time and place for such an outfit — and the White House just isn't it. In February, Karoline Leavitt was spotted wearing a below-the-knee leopard print dress and black knee-high boots. Although the ensemble was covered by a fairly boring coat, when that coat came off, Leavitt was certainly delivering some Adriana La Cerva from "The Sopranos" type energy. But as much as her boss likes to throw his weight around, make threats, and use bullying tactics to get what he wants, Trump is no Tony Soprano. In other words, Leavitt should have saved this look for the club.