This Frumpy Karoline Leavitt Outfit Is More Proof She Doesn't Know How To Dress Her Age

When people are accused of not dressing their age, the image that usually comes to mind is an older person clinging to trends from younger generations. However, White House Press Secretary Karoline Leavitt has flipped the script, often dressing as if she were older than she is. We've long argued that the "dress your age" adage should be banished from fashion discourse, but this feels like an exception. 

If Leavitt's wardrobe choices leaned vintage or had vibrant pops of personality, we'd be the first to defend her. Instead, she gravitates toward pieces that even fashion-conscious grandmas would politely return. Take the look she wore on July 3 during President Donald Trump's press briefing, for example. It was a joyless pairing of a plain black dress with a white jacket and a pair of outdated ballet flats. This outfit did nothing for Leavitt and, more importantly, failed to express her personality. 

We happen to know that this wasn't always how her wardrobe looked. Don't believe us? We discovered that Karoline Leavitt's outfits are making her look older simply by comparing her previous photos, which show outfits with personality and edge. But somewhere along the way, that spark got traded for press-room beige. What makes it worse is that Leavitt is one of the most prominent Gen-Z figures in the Trump administration. Whether Zoomers like it or not, she's their only real fashion representation in that space, and she's not doing them any favors.

One of the most recurring fashion mistakes Karoline Leavitt makes is choosing outdated patterns that are devoid of style and age her. Glam spoke to stylist Joseph Katz back in March 2025 about clothing colors and patterns that make you look older, and one of his top tips was to swap traditional check patterns for polka dots to keep looks fresh. But just a month later, Leavitt showed up wearing not just a check-patterned dress but also one made of brown tweed, which also tends to age the wearer if not styled well.

To make matters worse, she draped a beige cardigan over it like a security blanket. The heels were gorgeous, true, but they did little to elevate the look on their own. She also left a lot on the table, considering that tweed can be styled in so many ways. For example, the fall 2023 tweed trend gave it a preppy, stealth-wealth update that's easy to achieve if you put in a bit of work to modernize it — that means bright colors, nontraditional silhouettes, or at least a dash of personality. Unfortunately, Leavitt did none of the above.

One of the few highlights of Karoline Leavitt's closet is her willingness to experiment with color, a trait that is very Gen Z. Some of the biggest trends of 2025 have centered around bright manicure shades, blue dresses paired with statement shoe colors, and white dresses worn with metallic shoes for summer. Leavitt clearly got the memo on color, but unfortunately, that's where her ability to dress her age seems to stop. She often pairs cute shades with outdated silhouettes that do nothing to enhance or complement her looks.

A sad example of this is a stunning baby-blue outfit that could have been a slam dunk. The color made her hair pop and her skin glow, but it was completely sabotaged by a conservative pleated midi dress and a boxy cardigan that greatly aged her. One commenter pointed it out directly: "How can someone be so young yet look so OLD?" There are over 14 types of dresses that every woman should own, and yet Leavitt only seems to have one — and the oldest version of it at that.