Karoline Leavitt's Fashion Fails We Can't Ignore

Bursting onto the scene as the fresh new face of Donald Trump's second presidential administration, Trump spokesperson turned press secretary Karoline Leavitt is making waves and taking names. After Leavitt had a heated exchange with CNN's Kasie Hunt, it was clear she was destined to secure a golden position with the 47th President. However, being in the public eye also comes with its fair share of scrutiny from strangers, and Leavitt is not immune. Not only is Leavitt now trying to outrun plastic surgery rumors, she's also going to have to gear up for some rampant criticism about her wardrobe.

Typically the type of workwear that's expected on Capitol Hill errs on the side of professionalism, with suits, jackets, ties, and formality. Yet, when it comes to the Trump team, tradition is not usually their bag. For her part, Leavitt often taps into her Catholic roots and has been boasting some pro business looks — a sign she's taking her job as the country's youngest press secretary very seriously. However, not all of her outfits have hit the mark. In fact, some of Leavitt's fashion has failed her in miserable ways. Here's a peek at just a few of the outfits Leavitt might want to purge from her closet.

Coming off the heels of Karoline Leavitt's bruising 2022 congressional campaign defeat to Democrat Chris Pappas, the New Hampshire wannabe politician traipsed down to Aruba, Palm Beach in the Caribbean to nurse her wounds. In her Instagram post detailing her reasoning for the trip she stated, "A week to relax and reflect." However, one of the reflections she should have taken into consideration was her own in the mirror before wearing this swirl mess of a dress.

Still in debt after her failed congress run, maybe Leavitt was trying to save some money by pulling out a dress from decades past. But the marbled paper look is not really working. Not only that, but the colors are a bit too cacophonous, the pops of orange and purple don't blend well with the neon periwinkle background. Plus, the sheer bottom third is truly mysterious, ensuring that the look can't be cohesive. Too much is going on, but the smile on Leavitt's face indicates she was just happy to be away from chilly New Hampshire in the winter.

By March of 2023, Karoline Leavitt was ready to get back in political action and popped down to West Palm Beach, Florida "for business and pleasure," according to Instagram. During this time Leavitt was a spokesperson for Donald Trump and his presidential campaign, and was undergoing her unrecognizable transformation since being hired by Trump. Seen here in her signature pose (which is super cute and flattering) Leavitt is rocking an unfortunate error that's become part of this evolution. Incredibly fond of body-hugging jersey knit outfits, Leavitt pairs this similar style of fabric with a questionable pattern.

The zebra stripes, which are most likely supposed to create a waist-cinching illusion, give the appearance of a crease running down the middle of the dress. Not only that, but the pattern is overly busy and doesn't align well with the scoop neck top. The gray-green and cream color of the stripe pattern is also not quite perfect for Leavitt's glowing skin tone. Had the dress been all cream or all green, it would have accentuated her tan much better.

As spokesperson for Donald Trump's 2024 presidential campaign, Karoline Leavitt updated her headshots on Instagram in a rather questionable outfit. Boasting a new platinum blonde refresh, Leavitt is seen beaming in a black zip-up jacket with a crisp white button down underneath. This look does two things wrong. For starters, the jacket is much too casual and is rather reminiscent of a Dickie's work jacket — but even those have lapels. Plus, the buttoned all the way to the top look for the undershirt makes her look like a mean school teacher from the 1800s instead of a young and savvy communication strategist.

Leavitt even wore the outfit during an appearance on Newsmax to defend Trump when he was indicted in New York for his hush money trial. Although, in this appearance Leavitt unbuttoned that top button, as it must have been hard to communicate her ire with that in the way. Unfortunately for Trump, not even Leavitt's spitfire performance could save him from a guilty verdict in the case, which Trump, of course, used some choice words to express his disappointment over.

While Donald Trump was battling a bored crowd at his Madison Square Garden rally in October of 2024, spokesperson Karoline Leavitt was giving everyone something to talk about. In a post to Instagram, Leavitt is seen posing alongside Trump's director of media for his campaign, Sonny Joy Nelson. Joy Nelson is wearing a demure green dress with some suspicious sleeves, but Leavitt is seen dressed in what appears to be a black, fake leather dress. Pleather, which is mostly plastic, is a notoriously cheap material known for its popularity in the 1990s. As Leavitt falls into that uncanny valley of being on the cusp of Millennial and Gen Z, it would make sense she'd want to tap this look for an outfit. However, it appears this type of styling is a repeat offender for her.

Posing alongside the President on January 1, 2025, Leavitt once again donned a black dress with what could be fake leather detailing. Regardless of the quality of the potential leather, it shows up dull when photographed, which most likely isn't what the expert communicator is going for. Plus, the belt on the above dress almost appears as if it has been sewn in, instead of worn on top. Having a belt be a feature of a piece can often indicate low-cost, low-quality fashion, which is certainly not the vibe Leavitt wants to be putting off. 

As she started to settle into her position as White House Press Secretary, Karoline Leavitt took the time to pose with Communications Director Steven Cheung. With Washington, DC experiencing some chillier-than-usual temperatures in the winter of 2025, it would make sense that Leavitt would want to bundle up, but this all white outfit without a peek of skin is strangely off putting. First, the whites don't match. The jacket is a different tone than the ribbed dress which is a different tone than the knee high boots.

Once again finding herself straddling the styles of a Millennial mom and Gen Z upstart, Leavitt is reaching back to the wrong era of fashion with this outfit. Leather knee high boots were wildly popular in the 2010s, but have since faded away to make room for Chelsea boots and chunky sneakers. The midi-length dress is actually pretty cute, but that white is certainly a risk for any working mom to take (hope she has a Tide pen handy). And the jacket with its slightly fuzzy vibe can't seem to figure out if it wants to be professional or in a remake of "Clueless." Considering Leavitt is far from clueless, hopefully she can toss these 'fits to the curb during her White House tenure.