Karoline Leavitt's Leggiest Looks Of 2025 Were All Ruined By The Same Thing

Though she has the honor of being the youngest White House press secretary to ever serve, Karoline Leavitt has a history of dressing significantly older than she really is. This often has her sporting an eerie aura of being straddled between two worlds, with her face full of potential filler and her closet trapped in the post-war era. It's possibly this incongruence that has many arguing that Leavitt's MAGA makeover has ruined her sense of style. However, there have been times when she's tried to spice up her looks, although their success rate is debatable.

There's room to argue that the press secretary has undergone quite the transformation. From sporty college student to being embedded within Donald Trump's second administration, she's had quite the trajectory. One that occasionally seems to have Leavitt want to let loose her killer legs. Unfortunately, her combative grandma sensibilities often stand in the way of her being able to pull off a bold, leggy look. From tweed nightmares to too many pockets, there's ample evidence to suggest that Leavitt's leggiest outfits have been marred by her outdated sense of style.

For a January 2025 press briefing, Karoline Leavitt donned a leggy outfit fit for the winter weather. Seen in tights and knee-high boots, her look here feels disjointed and ultimately on the cheap side. Though this isn't the frumpiest dress Leavitt has ever worn, the red fabric appears overly stretchy and has too much going on. The false pockets and pleated hem are an homage to bygone eras, but on a fabric that most likely includes polyester, it makes the whole thing come off as bargain bin biddy.

During a press briefing celebrating President Donald Trump's first month of his second term in office, Karoline Leavitt donned the outdated look of a matching skirt and cardigan. A staple of most grandmas, the sweater set harkens to the post-war era as well as the "Clueless" era, although here Leavitt looks a little more 1950s than anything else. Though her black tights were most likely a tactic to keep the overly short skirt on the more modest side, they ultimately make the look into something Leavitt potentially dug out of her husband's closet.

Though Karoline Leavitt was all smiles next to President Donald Trump in this April 2025 Instagram snap detailing her "Walk and talk with POTUS to start the day," her outfit begs to differ. The sad beige cardigan is one of the trends we're begging Leavitt to ditch in 2026, and this photo is ample proof as to why. The bland oatmeal color does little for her complexion, and when paired with the tweed mini dress, it makes the overall look feel slightly depressed and at odds with her sunny sensibilities here. It would be wise for Leavitt to toss the outdated style and embrace her youthful glow.

In a classic Karoline Leavitt look that missed the mark, this deep blue quilted number from June 2025 did little to flatter the petite press secretary. Though there are ways to break the fashion rule of never wearing black with navy, Leavitt's pumps and bubble skirt don't quite make the cut. What's frustrating about this look is that it comes so close to working for Leavitt's small frame — it shows off her legs in a flattering way, and the cut of the skirt is youthful. But it's the texture and the giant buttons that ultimately make it look like Grandma's blanket.

Seen waltzing towards reporters outside the White House in July 2025, Karoline Leavitt flaunted quite the outdated outfit. Though she was possibly trying to show off her summer tan by revealing her gorgeous gams, the dress she chose ultimately felt more grandma than anything else. The heavy tweed looks itchy and surely uncomfortable for the warm weather, and the giant buttons do little to elevate the dress. Plus, the muted gray color does little to complement Leavitt's youthful skin tone, making the whole thing feel off-kilter.

Spotted in an August 2025 Instagram snap celebrating being "West Wing girls," Karoline Leavitt is surrounded by Meghan Bauer and Melania Trump lookalike Margo Martin. While no one is nailing their look in this photo, Leavitt was at least trying to show a little leg for the summer moment. However, once again, Leavitt's outdated sense of style did her dirty and left her vulnerable to yet another grandma fashion fail. The pleated tweed skirt is not only tacky, both figuratively and, most likely, literally in the humidity of Washington, D.C., but it also looks overly cheap. Not the chicest look for someone who surely lives the luxe life.