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Cheperdak, a former White House staffer from Trump’s first term, is renowned for her expertise in modern etiquette across professional and social environments. Her career spans roles in news media and the legal field, including a stint as a clerk and attorney advisor at the U.S. Treasury. She ventured into etiquette consultancy after leaving the White House in 2021. In an essay for The Conservateur, Cheperdak reflected on her career shift, stating, “For me, the pivot was unexpected. I took a turn into entrepreneurship. I saw how much etiquette can help you in work and in life — and how the absence of it can quietly hurt you.” (Trump himself might benefit from her lessons.)
Cheperdak fits the typical profile of the women in Trump’s circle: blonde, white, and fit. However, she distinguishes herself by not appearing reliant on cosmetic enhancements, unlike some of her counterparts. Moreover, her keen fashion sense and apparent disinterest in stereotypical Republican makeup set her apart.
Anyway, the thing here is she fits exactly into the mold of women Trump usually surrounds himself with. One, she’s blonde. Two, she’s white. And three, she seems physically fit. But what sets this woman apart from those in Trump’s inner circle is that Cheperdak doesn’t seem addicted to lip fillers and plastic surgery (no shade to Leavitt). She actually has good fashion sense, as well, and doesn’t appear to be a huge fan of the so-called Republican makeup.
Even amidst Trump’s legal battles, it’s hard to overlook the consistent presence of similarly styled women around him. Author Michael Wolff noted, “There is always an entourage of … younger, good-looking women around Trump, all dressed the same and all who basically look the same.” These women often mirrored the appearance of First Lady Melania Trump, who was notably absent during this time. Wolff mentioned Hope Hicks, Madeleine Westerhout, and Natalie Harp as examples. “I spoke to one of the jurors. He said, ‘All of these Trump women, girls, you know, the ones who were testifying… They all dress the same and they all look the same,’” highlighted the biographer.
Donald Trump has a certain type
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For years, it’s been said that Donald Trump has a preference for women working in his administration. The author and Trump critic Michael Wolff said in his time observing the White House for his book, he noticed a striking pattern among women going around the West Wing halls. “Sitting there every day, […] I would see these women come by all who were dressed the same,” he said on “The Daily Beast” podcast. They usually came in wearing tiny pencil skirts (“this was during the winter”) and knee-high boots instead of proper heels. He found this bizarre. “You know, and I texted my wife saying, ‘God knows I could have missed some fashion trend, but I said, is this unusual?’” Wolff recalled. “‘Yes,’ she said. ‘This his would be very unusual if they are all, in this singular mode.’”
Even during his hush money trial, it’s hard not notice that Trump surrounded herself with women who all look like clones. “There is always an entourage of … younger, good-looking women around Trump, all dressed the same and all who basically look the same,” Wolff pointed out. Most often, they looked like clones of First Lady Melania Trump, who had all but vanished during that period. He cited Hope Hicks, Madeleine Westerhout, and Natalie Harp as examples. “I spoke to one of the jurors. He said, ‘All of these Trump women, girls, you know, the ones who were testifying… They all dress the same and they all look the same,” stressed the Trump biographer.
As for Trump’s newly hired etiquette instructor, we’ve yet to see whether Alison Cheperdak will play a much bigger role in this current administration. More likely the answer is no, but wouldn’t it be great if she taught POTUS a thing or two about manners?