Leavitt’s sense of fashion, however, feels anything but celebratory.

But these are just two examples of Leavitt’s fondness for demure doily-inspired dresses.

Here’s five times Leavitt dressed significantly older than she really is.

Karoline Leavitt approaches a group of reporters outside the West Wing (2025)

In an Instagrampostsimply captioned “WOMEN FOR TRUMP,” Leavitt is surrounded by some of the MAGA elites.

However, despite being the youngest in the bunch, Leavitt picked the dowdiest clothes to wear.

In her pastel pink top and morbid black cardigan, Leavitt looks ready for a bingo hall.

Sarah Huckabee Sanders, Tulsi Gabbard, Danica Patrick, Karoline Leavitt, Lara Trump, and Kristi Noem pose together (2024)

When the couple was finally ready to tie the knot, Leavitt certainly chose quite the questionable wedding dress.

The beading creates an art deco-inspired look, which is great for architecture but tricky for clothing.

It’s an interesting choice for Leavitt to have in her closet.

Nicholas Riccio and Karoline Leavitt hold hands on their wedding day

But Leavitt’s sweater set conjures up an image closer to pearl-clutching than self-idealization.

It could be that Leavitt is trying to fit a throwback-inspired mold, but she’s ultimately falling short.

Even her youth cannot save Leavitt from dressing like a reanimated Molly McIntire American Girl Doll.

Karoline Leavitt arrives for a White House press briefing at the White House (2025)

Once again swimming in a boxy cardigan, Leavitt’s overall outfit is not just dated, but ill-fitting.

However, it leaves much to be desired.

Instead, Leavitt appears insistent on becoming the real-life embodiment of the character Angela from “The Office.”

Karoline Leavitt walks up to a group of reporters outside the West Wing (2025)

Karoline Leavitt speaks with reporters outside the White House (2025)