Karoline Leavitt's Outfits Are Making Her Look So Much Older

If you had to guess Karoline Leavitt's age based on her public appearances, 27 probably wouldn't be your first pick — but that's exactly how old she is in 2025. Born in 1997, Leavitt is by all accounts Gen Z, even though her wardrobe bears no hint of this. From grandma sweaters to schoolteacher skirts and prim blouses, the White House press secretary is particularly fond of oversized matronly maxi dresses that do her no favors.

She makes all the outdated clothing mistakes that instantly make you look older; think frequent pantyhose, shapeless silhouettes, and head-to-toe black with zero contrast. She also gravitates toward ditzy patterns and washed-out colors that are really popular with the older generation and rarely seen with her younger peers. As a result, when she poses with the 40-and-up Mar-a-Lago crowd, as seen on Instagram, she blends in a little too well.

Now, to be fair, Leavitt isn't the only Trump-world woman with a history of fashion missteps (Kimberly Guilfoyle's inappropriate outfits forever haunt us). However, the White House press secretary is the only one with a vastly unwavering record. And when you factor in other elements of her life, like her traditionally styled home and a husband 32 years her senior, the dots start connecting. Is "grandma chic" just Karoline Leavitt's personal style, or is there something deeper behind her wardrobe choices?

A dive into Karoline Leavitt's older Instagram posts, before her failed congressional run, much older husband, and federal appointment, reveals a completely different side of her. It's true that she always aligned with the pro-Trump crowd, but her wardrobe used to tell a younger, chicer story. She was clearly proud of her body and knew how to appropriately show it off in cute summer dresses, pants, and blouses.

Fast forward a few years, and everything she wears now is oversized and hits below the knee without a hint of cleavage in sight. Our theory? Karoline Leavitt is actively distancing herself from the unique traits associated with Gen Z. Let's face it: Zillennials don't exactly have the best workplace reputation among older generations, who still hold most of the power. And as the youngest White House press secretary in history, Leavitt can't afford a single misstep that might spark comparisons to how an older, more "experienced" person might handle the job.

Between her aging wardrobe and older husband, Leavitt isn't being viewed through the same lens as most working-class Gen-Z professionals. More impressively, her outfit choices prove just how powerful fashion can be. She's carefully curated a persona through clothing, and though the result is painfully drab, the strategy is undeniably smart. But here's the twist: It is possible to look mature and respectable without leaning into a wardrobe that feels stuck in another decade.

Regardless of how sus Karoline Leavitt's shift to ultra-mature fashion may seem, one thing's for sure: Style is customizable. There are countless style secrets that can help you look older without showing up like you raided a retiree's closet. Stylish doesn't have to mean scandalous, and there's a whole lane of grown-up fashion that still feels fresh.

For starters, she could trade in the oversized 'fits for tailored pieces. Think silk trousers, which are a timeless workwear staple that flatter without overexposing. Buttoned-up midi-skirt suits with a cinched waist are another great option that strike a balance between experienced and effortlessly modern. And tailored vests are the perfect workwear to look casual without sacrificing dominance.

Leavitt's makeup game could also use a refresh. Right now, she leans into heavy foundation, dusty mauve lip shades, and eye makeup that doesn't flatter her features. A more natural base, a hint of pink on the lips, and a lifted eyeshadow look could work wonders and help her lose the tired effect. These changes won't give "Gen Z queen" energy, but they also won't age her into oblivion.