Karoline Leavitt's Magenta Monochrome Moment Is An Ill-Fitting Mess

How is it possible that America simultaneously has the youngest-ever and oldest-ever White House press secretary in office right now? Karoline Leavitt may only be 27 and a member of Gen-Z, but she clearly shops at stores primarily frequented by Baby Boomers. On April 29, 2025, the New Hampshire native gave a press briefing and decided to wear some kind of magenta matching set that just screams: "I'm an 80-year-old woman trapped in the body of a twenty-something!"

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The monochromatic outfit doesn't fit well and makes her look much older than she is (closer to Leavitt's husband Nicholas Riccio's age, in fact), which sadly seems to be the Trump staffer's go-to style. Before becoming press secretary, the mother of one dressed in attire much more reflective of her own generation, but that era has apparently ended. Now, Leavitt wears expensive outfits reflective of her wildly lavish life that, regardless, age her considerably. Suffice it to say that many of Leavitt's fashion choices have missed the mark and this nightmare-inducing magenta monochrome, two-piece matching set is definitely among them.

Besides dressing like she's in her 80s, that magenta getup wasn't the first time that Karoline Leavitt sported a monochromatic look. In April 2024, the youngest White House press secretary in U.S. history donned an all-green outfit that would even offend Kermit the Frog. She posted a couple of photos to Instagram, showing off her then-baby bump, but the pea soup-colored green fabric stole the spotlight. 

Leavitt also rocked a full baby blue-inspired outfit back in March 2025, which she also shared on Instagram. That color was much easier on the eyes than that green monstrosity was, but the cardigan matched with the long pleated skirt made her look more like a stereotypical sister wife from a past era rather than a young woman living in modern times.

And, in October 2023, the future Trump staffer donned a red dress with some kind of matching choker attached to it. She snapped a picture of the outfit while hanging out in Boston, Massachusetts. "The birthplace of the American Revolution. I love this city," Leavitt captioned the post on Instagram. This dress would actually work for her if it didn't have that bizarre neckwear attached. We wonder what monochromatic color she'll wear next.