Karoline Leavitt's Pre-Trump Daisy Duke Outfit Looked Painful To Wear

Karoline Leavitt has been dressing way older than she is since taking on the role of White House press secretary in January 2025. Yet, it seems that her style wasn't always this way. Photos of Leavitt before she joined the Trump administration show that she used to have a very different sense of style — an aesthetic that was at least more age appropriate. That doesn't mean, however, that she wasn't still sporting fashion fails we couldn't ignore. One outfit, in particular, almost makes us happy she started wearing the wardrobe she sports today ... almost.

Leavitt became the youngest White House press secretary in history when she got the gig at the age of 27. Less than two years prior, though, she was just a normal 20-something posting photos with pals on Instagram. In 2023, she shared a June photo dump on social media, which featured a photo of her holding a "Trump Make America Great Again" sign as the first image. Another photo in the series showed her signing merch for someone wearing an "impeach Biden" T-shirt. Evidently, some things never change. What has changed since then, though, is her tendency to actually dress like the young woman she is. One photo showed her sporting some Daisy Dukes. And, in this case, the term "beauty is pain" isn't exactly correct. Just because an outfit looks painful doesn't mean it's cute.

One of the photos in Karoline Leavitt's Instagram carousel showed her posing with pals. Each of the friends was wearing denim shorts for the occasion, but no one's shorts were quite as short or as form-fitting as Leavitt's were. She paired her Daisy Dukes with a black Gucci belt, matching cowboy boots, and a tucked-in beige tank top. We imagine that sitting down in an outfit like this would be a bit on the uncomfortable side, and it's possible that this is one reason why it's a far cry from the stuffier-looking outfits we see her sporting today.

The Daisy Dukes are the part of this photo that probably caught most folks' attention first. With another glance, though, it's interesting to note that Leavitt was nearly unrecognizable before she formally joined Donald Trump's circle. Based on this picture, it's easy to see why Leavitt can't escape plastic surgery rumors. She didn't yet have her try-hard pout that may come from lip fillers, and she's smiling in a relaxed way that has seemingly been completely replaced with a stern scowl these days. While the micro shorts may look a bit uncomfortable, the photo makes it easy to wonder if she felt happier and more like herself in the Daisy Duke-clad good old days.