Karoline Leavitt Has Flaunted Her Killer Legs More Than Once

Before becoming the youngest ever White House Press Secretary, Karoline Leavitt made sure to pack in a full life. Now that Leavitt is holding daily press briefings, going on the offensive for President Donald Trump and his second administration, it seems she's pivoted her style to reflect such a major career change. Leavitt, a Gen Zer, has become known for wearing outfits that skew into a higher age bracket. Often covering up the entirety of her tiny frame, Leavitt seems to prefer a matching cardigan set over a sleek, sophisticated pantsuit. While it's well within her right to dress however she wants, this new sense of style is a departure from the days where Leavitt loved to put her legs on display.

Before entering the White House, while she was helping Trump with his presidential campaign, Leavitt often opted to wear outfits that showed off just a bit more skin than her current American Girl Doll looks. It could be that now she's a wife and mother, Leavitt feels the need to leave her beach bikini days behind her. Or maybe the chilly winter and spring climate of Washington, D.C. has seeped into her bones. Whatever the case may be, there are still plenty of moments before Leavitt underwent her transformation to become press secretary where she felt comfortable showing off her killer legs.

Seen here in a July 16, 2023 Instagram post, Karoline Leavitt felt the need to show off the labor of some surely grueling workouts. With the quaint caption of, "Nantucket, you're cute," Leavitt seems to be wanting to be told that she, also, is cute. Smirking in her dark workout onesie, Leavitt looks ready for anything from the gym to the sea. The spandex of it all makes the fit hug her body nicely, and her pose really does show off her gorgeous gams. It's safe to say that this is not one of Leavitt's outfits that have missed the mark.

Leavitt's stop in Nantucket, Massachusetts was just one of many luxurious vacations the pintsized powerhouse goes on. During the span of 2018 to when this photo was taken in 2023, Leavitt had been to Rome, the Swiss Alps, Amsterdam, England, Greece, and managed to vacation in gorgeous parts of the United States. It seems Leavitt was trying to pack in as much adventurous youth as she could before settling down with her much, much older husband. Luckily those adventures also included getting to show off her legs before seemingly putting them away for a while.

Continuing to soak in the sun and sea in Salisbury, Massachusetts, in July 2023, Karoline Leavitt posted to Instagram that she was enjoying a "Beach day with my beach bum." The corresponding photo shows Leavitt tossing a child in the air (most likely a nephew as Leavitt wouldn't welcome her son for two more years). What is clear from this photo, though, is just how happy Leavitt is to be on the beach, as well as boasting incredibly tanned legs to match.

Sure, there are some flaws to this outfit — even a simple bikini at the beach can have downfalls. The floppy hat does feel a bit over the top, just because it's recommended to wear sunscreen and protect your skin from the sun while at the beach doesn't mean you have to wear something embarrassing. And the bikini choice of Leavitt is also just a bit bland, and the color brown feels off for her skin tone, especially when she's this tan. Luckily the legs save the day, carrying the weight of some poor fashion choices (and being strong enough to help her toss a child in the air).

Before dressing in all pink to try and be White House Barbie, Karoline Leavitt tried out a blue phase. Posing for an Instagram post, Leavitt is seen in a sports bra and matching cobalt leggings. Standing in front of Lake Tahoe, Leavitt's caption says, "If Heaven were a place on Earth... it would be here." While these leggings appear to cover up more of Leavitt's legs than some of the other outfits on this list, they still manage to show off her toned features in a casual way.

The laid back and low key hair she's rocking here is a nice break from Leavitt's nursing home-inspired White House looks. In fact, this whole outfit is a reminder that Leavitt used to at least want to act and appear her age. As someone in their late 20s, the style Leavitt is bringing to her position within President Donald Trump's second administration is one full of frump and fillers (well, potential fillers, anyway). To see her living a life where getting a tan and strolling on the beach was a big priority comes as such a shock now. Hopefully she can find time to take a break from spewing questionable answers from the press podium to reconnect with this version of herself. 

While serving as national press secretary for Donald Trump's 2024 presidential campaign, Karoline Leavitt hit the road to promote Trump any way she could. A photo published to her Instagram on March 5, 2024, shows a behind the scenes glimpse at what some of that job description entailed. Seen smiling in a bright pink blazer and plain black dress, Leavitt's caption simply states, "Warming up the crowd for 47." Sitting across from her is Brian Glenn, boyfriend of controversial republican Marjory Taylor Green. While it's clear the intent of the photo is to show how Leavitt fulfilled her role while on the road, what takes center stage is actually how short her dress accidentally is here.

Crossing her legs at the ankle like a true demure professional, Leavitt does a great job of downplaying how much skin she's showing. Whether on purpose or by accident, the simple little black dress Leavitt chose to wear for the event got even smaller when she took the seat across from Glenn. Strangely, this is one of her more coordinated outfits. It's a classic look — a large blazer over a tiny dress is always an easy way to elevate what could be a boring outfit. What makes this piece so shocking is how far she's moved away from this type of style, especially now that Leavitt is opting to wear frumpier dresses.

On September 10, 2024, Donald Trump and Kamala Harris verbally sparred in the only debate between the two presidential candidates. Even though Trump refused to return to share the stage with Harris after the event, Karoline Leavitt still took to Instagram to claim victory. Posting a snap of herself in front of a presidential debate-themed step and repeat, Leavitt wrote the caption, "Debate Night W," indicating that she thought Trump had won the exchange. The outfit Leavitt chose to wear to celebrate taps into the nostalgia of the movie "Clueless," which is full of matching patterned blazers and mini skirts.

This type of tailored blazer has a fun and effortless feel, as opposed to the stiff and boxy "Little House On The Prairie" sweaters Leavitt has been wearing more recently. The pattern is a fantastic refreshed classic, and her matching pink shirt makes the whole thing work. Plus, the short skirt allows Leavitt to show off her legs in a way that still fits with the vibes of the outfit. If anything, this is a great example of what a 20-something staffer in the White House could be wearing to remind everyone she's still young and fun. Instead, Leavitt has continued to choose more covered-up and dowdy fashions as press secretary. Which is well within her right, but still a bit concerning that a mother who isn't even 30 yet wants to dress like a grandma.