5 Times Karoline Leavitt Has Rocked Leggy Looks

Since becoming the White House press secretary, Karoline Leavitt has shown her true colors time and time again. Not only is she unable to be truthful, most recently lying about whether the "big, beautiful bill" her boss has been touting will add to the deficit, but she has a penchant for shutting out reporters who dare to question the administration's agenda. Leavitt was one of the driving forces behind getting ABC News correspondent Terry Moran suspended because he called Trump a "world-class hater."

If lying to the American people and being rude to respected journalists wasn't enough, Karoline Leavitt fails in other ways too. She continues to wear outfits that totally miss the mark, she can't seem to leave behind one blatantly outdated accessory, and she actually managed to butcher the butter yellow color trend. By all accounts, Leavitt is a Trump devotee and, to make matters worse, she doesn't have a fashionable bone in her body.

To add to these egregious offenses, Leavitt has convinced herself that wearing leggy looks in a professional setting is a good idea. Granted, not much about the Trump administration is exactly professional, as evidenced by its rhetoric, but at the end of the day, there's a time and place for everything. Something that Leavitt doesn't appear to understand, based on her leggy looks.

Karoline Leavitt loves a frumpy look. In fact, Leavitt's worst outfits all have one thing in common: they're created for older people. Like her 59-year-old husband, for example. If you look closely at a lot of Leavitt's outfits, whether they're leggy or not, they have a cheapness to them in both design and detail. Most women in their late 20s aren't running around with rhinestone buttons. That is, except Leavitt. Even the thread in this dress she wore in March 2025 appears to have some shimmer to it that it just shouldn't. 

To make matter even worse, there's this hemline. It's not just that it's a little too short to wear to work, but the way the last few inches have been slapped onto this dress isn't just frumpy, but outdated. Everything about this look is a reminder of how much prestige is no longer part of the White House.

In March 2024, Karoline Leavitt made a campaign stop for Trump. Although the event was probably casual in nature, you'd think Leavitt would dress with a bit more decorum, especially while representing a former president and presidential candidate. After all, Leavitt appears to respect and trust Trump, so you'd think she'd be a little less leggy in her campaign looks. Plus, she just looks straight up uncomfortable in this outfit, with her knees and ankles locked together.

Miniskirts have to be one of the best items of clothing ever designed. No matter your age or body shape, they always look fun with a bit of sass. While this may have been the look Karoline Leavitt was going for during the presidential debate in September 2024, she missed it by miles.

Instead of looking like someone who was about to embark on a career in politics, she looked like she was on her way to pledge a sorority, but got lost and ended up at a presidential debate instead. It's impossible to take Leavitt seriously in this leggy outfit. And once we add in the fact that it looks like a cheap attempt at a Chanel suit, it makes Leavitt look even sillier.

Just when you think Karoline Leavitt dresses too young for her age, she does a 180 and looks like she got into her grandmother's closet. Although the Trump family women are notorious for not giving up outdated trends, it doesn't mean Leavitt has to follow suit — yet here she is, strolling around the grounds of the White House dressed like her grandma on her way to tea. 

While Leavitt may be doing her leggy thing, she's going for it in an outfit that's bland from head-to-toe. After all, who under 60 is wearing such a boring plaid getup? While there's nothing wrong with the cardigan, given what Leavitt has paired it with, the outfit as a whole is just a miss all around. It really makes one wonder why she's smiling, especially given her bland shoe choice, a trend that appears to be taking MAGA women by storm.

Back in July 2022, Karoline Leavitt joined her buddy and former White House press secretary Kayleigh McEnany at an event that Leavitt was clearly not dressed for. Wearing a short, lemon yellow cotton dress and open-toed sandals — and rocking one heck of a tan — Leavitt looked like she was ready to have cocktails with her friends after a long day at the beach. In no way did she look like someone who should be taken seriously in the political arena: an image she has taken with her into the White House.