A Shift in Fashion Choices
When people talk about dressing their age, the common image that comes to mind is an older person trying to keep up with younger trends. However, White House Press Secretary Karoline Leavitt has taken a different approach, often appearing older than her actual age through her wardrobe choices. While we have long believed that the “dress your age” rule should be removed from fashion discussions, Leavitt’s style seems like an exception.
If Leavitt’s clothing choices leaned toward vintage or had vibrant personality, we would support her. Instead, she tends to wear pieces that even fashion-conscious grandmas might find outdated. For example, during a press briefing on July 3, she wore a plain black dress with a white jacket and outdated ballet flats. This look lacked any flair and failed to reflect her personality.
We know that this wasn’t always how her wardrobe looked. By comparing her previous photos, we can see that she once wore outfits with more personality and edge. However, at some point, that spark was replaced with a more muted, press-room beige palette. 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 is their only real fashion representative in that space, and she’s not doing them any favors.
Outdated Patterns and Aging Looks
One of the most recurring fashion mistakes Leavitt makes is choosing outdated patterns that make her look older. In March 2025, stylist Joseph Katz spoke about clothing colors and patterns that make you look older, suggesting that traditional check patterns should be swapped for polka dots to keep looks fresh. Yet, just a month later, Leavitt wore a check-patterned dress made of brown tweed, which tends to age the wearer if not styled well.
She also draped a beige cardigan over the outfit, resembling a security blanket. While the heels were beautiful, they did little to elevate the look on their own. She missed an opportunity to modernize the tweed, as the fall 2023 trend gave it a preppy, stealth-wealth update that could have been achieved with bright colors, nontraditional silhouettes, or a dash of personality. Unfortunately, Leavitt didn’t take any of these steps.
Color and Silhouette Mismatch
Leavitt has a tendency to experiment with color, a trait that aligns with Gen-Z fashion. 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 her ability to dress her age seems to stop there.
She often pairs cute shades with outdated silhouettes that do nothing to enhance or complement her looks. A sad example is a stunning baby-blue outfit that could have been a hit. The color made her hair pop and her skin glow, but it was completely ruined by a conservative pleated midi dress and a boxy cardigan that aged her significantly. 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, but Leavitt only seems to have one — and the oldest version of it at that. Her fashion choices seem to lack the creativity and modernity that could help her represent her generation more effectively.
