Karoline Leavitt's 'Grandma Chic' Moment With Margo Martin Is Giving Sewing Class Dropout

Since she took the job as White House Press Secretary, there's been a lot of buzz about Karoline Leavitt's youth. At a recent White House event, the 27-year-old mentioned that she's part of Gen-Z, or, to get more technical, "Zillennial, 'cause I'm right on the cusp of millennial and Gen Z" (via Instagram). When it comes to fashion, however, Leavitt's preferred style consistently skews way older -– a couple of generations older. This contrast is even more evident when Leavitt hangs out with her peers, as illustrated in a May 2025 Instagram carousel posted by Margo Martin, Donald Trump's special assistant and communications advisor. Like Leavitt, Martin's been with the Trump team for a while, formerly serving as deputy communications chief.

Martin, who's 28,opted for a classic all-black combo of pants and a double-breasted jacket, and Leavitt chose her usual grandma-esque look. The press secretary wore a midi-length skirt, an embellished cardigan, and a shirt with prominent bell-shaped cuffs. A closer pic reveals Levitt's sweater is replete with bead-dazzled additions on the neckline, pockets, and front of the sweater. While this is hardly surprising, what really stands out is that Leavitt needs tailoring. At five feet four inches tall, she's right on the border between shorter and regular length sizes. Here, her skirt looks a bit too long. In addition, the extra length on her sleeves seems unnecessary, especially since the material swallows up most of her hand. In the close-up shot, Leavitt even has the cuff flipped back to get it out of the way.

As colleagues, Karoline Leavitt and Margo Martin likely spend a lot of time working together, and on some occasions, their fashion has been in sync, whether it's similar styles or color palettes. For instance, during the 2025 Super Bowl, both women wore black dresses, albeit with a couple of twists. Martin's lighter-weight dress required her to top it with a jacket to ward off the chill, while Leavitt showed her love of leather. Here, accurate sizing made all the difference in Leavitt's look. The press secretary's choice of material was perfect for the weather, and the hem hit just above her knee. The long sleeves ended in two tighter cuffs, precisely at Leavitt's wrists, similar to a button-down shirt.

Unfortunately, sometimes, their similar fits reflect Leavitt's stereotypical grandma style. In a pic from October 2024, Martin and Leavitt wore white dresses with pleated skirts. Martin's dress may have lacked Leavitt's nautical stripes, but they both had tacky, over-the-top large buttons that would be better left many decades in the past.

Martin also copied Leavitt in her May 2025 Instagram photo dump. Although they're not together in the photo, Martin is wearing a bland cardigan with more giant buttons. Tall and with long, brown locks, Martin resembles Melania Trump, and she was even mistaken for Melania when she wore sunglasses at Donald Trump's June 2023 court proceedings. Not here, though — it looks like Martin got cold at work and Leavitt lent her a sweater.