From Laura Bush's Red Dress to Melania Trump's Jacket, Why a First Lady's Fashion Is Politics

Win McNamee/Getty Images; Chip Somodevilla/Getty; Arnaldo Magnani/Getty From left: former First Ladies Michelle Obama, Melania Trump and Laura Bush

It was early on in the George W. Bush administration when then-First Lady Laura Bush made a trip to the Ronald Reagan Presidential Library in Simi Valley, California. The occasion was an exhibit of the most notable ensembles worn by Nancy Reagan, a first lady who loved to dress up (and was, more often than not, criticized for her expensive taste in clothing).

Seeing firsthand the popularity of the exhibit underscored for Mrs. Bush the importance of the sartorial choices made by a first lady — and the fact that she'd likely face criticism no matter what she wore.

"[Nancy Reagan] told Mrs. Bush at the time: 'You know all those clothes I was criticized for? Now they're lining out the door to see them,' " Anita McBride told PEOPLE in a recent interview.

McBride, Mrs. Bush's chief of staff, says that the simple act of getting dressed is "always a conundrum for first ladies."

"There are first ladies who are generally interested in fashion and follow the trends, but all first ladies, Laura Bush included, really do feel this sense that all the eyes of the world are upon them," she says. "So dressing the part of a first lady takes on an entirely different dimension due to that pressure."

As Hervé Pierre, who was the first lady's stylist while Melania Trump was in the East Wing, explained to Women's Wear Daily in January: "It's not just like [finding something for] a black tie or a cocktail party. You have all the glamour, but then you also have hospital visits and everything else. The panorama of the wardrobe for a first lady is so big because there are so many events that need to be fulfilled."

"Politics and pleasing the eye," Pierre said, "are two completely different things."

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For her part, while Mrs. Bush "was never much of a clotheshorse," McBride tells PEOPLE she made some important sartorial choices early on in her husband's White House tenure: one, that clothing could be directly connected to policy; and two, that even first ladies should be able to recycle the clothing they wear.

"I think one of the things that was important for her was connecting the fashion to the policy," McBride says.

That was evident in the first lady's role as honorary ambassador of the Red Dress Project for heart disease. "She felt that nothing attracts attention like a red dress and it was the perfect symbol: Even a little red dress can save lives," McBride says.

Arnaldo Magnani/Getty Laura Bush

Mrs. Bush wasn't the only first lady to realize that fashion could have an impact. Donald Trump's wife made perhaps one of the most notorious sartorial choices of any first lady when she donned a Zara jacket that read "I Really Don't Care, Do U?" on a 2018 trip to a migrant child detention center amid the rollout of her husband's divisive immigration policies.

In a subsequent interview with ABC News, Mrs. Trump insisted the jacket wasn't meant as a message concerning immigration but was instead "for the people and for the left-wing media who are criticizing me. I want to show them I don't care. You could criticize whatever you want to say. But it will not stop me to do what I feel is right."

Her spokeswoman at the time, Stephanie Grisham, went on to refute this in a book, however: Grisham wrote in a recent memoir that Mrs. Trump had bought the Zara jacket herself and seemed unaware of the signals it sent during her trip. According to Grisham, President Trump was the one who said they should argue the message was intended for the press.

Grisham had more fashion stories to relay in her tell-all, including how the first lady dressed — inadvertently or not — like "a Safari Barbie" for her solo trip to Africa in 2018.

While aides and Mrs. Trump deliberated the clothing choices at the time, Grisham writes, "One person in the group ended the discussion with a very definitive 'Ma'am, they're going to beat you up no matter what. I say wear it. You look fabulous, and you're a fashion icon!,' and with that she gave us one of her intoxicating laughs."

Chip Somodevilla/Getty Melania Trump

Other first ladies have made statements via their outfits in different ways. President Dwight D. Eisenhower's wife, Mamie Eisenhower — whose personal style was largely eclipsed by the first lady who succeeded her, Jacqueline Kennedy — enjoyed dressing "fashionably but also sensibly," White House historian Lina Mann tells PEOPLE.

"She was used to not making due with much, so she shopped for bargains," Mann says.

Mrs. Eisenhower was largely responsible for popularizing the 1950s American housewife look: one piece, full-skirted shirtwaist dresses worn with lots of jewelry.

"She loved to accessorize, so she would have a full set of jewelry with a double- or triple-chain of pearls, matching earrings and a signature charm bracelet which featured 20 charms featuring 20 points in her husband's career," Mann says.

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Like Mrs. Eisenhower, Mrs. Bush did not have a personal stylist during her time in the White House, opting instead to work directly with designers, such as Oscar de la Renta, who dressed her for many occasions.

Hillary Clinton also had close relationships with designers, including Ralph Lauren and Calvin Klein, both of whom designed a look that became her signature: the pantsuit.

Meanwhile, incumbent First Lady Dr. Jill Biden has strategically remained mum on her fashion choices, though they haven't been immune to (even minor) buzz.

"It's kind of surprising, I think, how much commentary is made about what I wear or if I put my hair in a scrunchie," Biden said in an interview for Vogue's August cover story.

In his WWD interview in January, Pierre reflected on the scrutiny of the role: "The next stylist for the first lady will be jumping into a situation that is — I don't want to say James Bond-like — but it is very mysterious and secretive."

PAUL J. RICHARDS/AFP via Getty Bill (left) and Hillary Clinton

Even in centuries past, stylists have proven an integral part of a first lady's team.

"A good early example of someone working with a specific [stylist] was Mary Todd Lincoln," Mann, the historian, says. "She worked with a seamstress named Elizabeth Keckley, who was formerly enslaved and developed a robust seamstress business. She became her main designer, and that was pretty early on in the 1860s, so there is precedent for that."

The relationship wasn't immune to scandal, however.

After President Abraham Lincoln was assassinated and his widow left the White House, she made what would become an ill-fated visit to New York.

"She didn't have a lot of money, so she and the seamstress took this trip and tried to sell their gowns and it became a public scandal several years later when Keckley wrote a memoir," Mann explains.

In recent years, stylists have become even more important to first ladies.

Michelle Obama, for instance, has forged a strong relationship with Meredith Koop, who helped conceive of some of the former first lady's most iconic looks, such as the thigh-high Balenciaga boots she wore to close out her 2018 book tour.

"Working with Balenciaga and commissioning that look was a risk. I didn't know if she would go for it because it's not something everyone is going to get or like," Koop told PEOPLE in a recent interview. "It's bold, it's different and it's challenging. The fact that she rocked it was a reflection of her power, her confidence and her presence. It was part of her coming into her new chapter as Michelle Obama."

Getty Former President Barack Obama and former First Lady Michelle Obama arrive to President-elect Joe Biden's inauguration on Jan. 20 at the U.S. Capitol

Working with couture designers on bespoke creations is certainly par for the course for most first ladies, but many have opted to don clothes that everyday Americans can also access.

As Mann explains, Eleanor Roosevelt wasn't known for high fashion, "but what she represented is notable because she came to the presidency in the middle of the Great Depression and World War II followed that — so her style tried to focus on practicality, clothes that were easily made and could be worn for multiple occasions."

The inaugural gown worn by Franklin D. Roosevelt's wife in 1933, for instance, came with detachable sleeves, so it could be worn for everything from an evening event to a daytime party.

Decades later, Mrs. Bush was also careful to recycle her clothing, McBride says: "A dress worn to White House correspondents' dinner in the spring, for instance, she could also maybe wear to the Congressional Ball in December."

There is, however, a downside to wearing the same thing twice.

"Almost everything you wear as first lady is catalogued," McBride says. "For each outfit, a personal aide will write down where it was worn and when on a little card placed in a plastic sleeve with each sort of outfit. This way you are sure not to wear it to the same event a second time."

Of course, the cataloguing only extended to the most heavily-photographed outfits, McBride notes — which presented a problem.

"One day, Mrs. Bush had an interview with Chris Wallace," McBride recalls. "So she showed up on Sunday morning and was waiting in the green room watching the show and they were showing previous footage of her to announce her appearance. Of course, in the footage she was wearing exactly the same thing she had on in the green room."

After quickly switching outfits with her press secretary in the green room, Mrs. Bush then ran onto the set for her interview.

AFP/Getty Jill Biden

It wasn't the only time she had to hastily change her ensemble. McBride remembers another instance — the Kennedy Center Honors in 2006 — in which she purchased a brocade lace dress off the rack from Oscar de la Renta.

"Prior to the honor, Laura shook hands at a private White House reception. Imagine her surprise when, in the receiving line, there was not one, not two — but three women wearing the exact same dress," McBride says.

In the intervening moments that between the reception and the event at the Kennedy Center, McBride says Mrs. Bush went upstairs to the residence and changed into a different gown. ("Even with fashion, there can be mishaps along the way.")

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Of course, there can also be wonder, such as in the case of a plum-colored flared trouser and turtleneck look designed by Black designer Sergio Hudson for Obama at the 2021 inaugural ceremonies.

"The Sergio Hudson look was, for me, about excellence, perseverance and, again, confidence," Koop told PEOPLE, adding: "For these big fashion moments, I try to reflect Michelle's evolution and the overall moment. It doesn't always coalesce — but when it works, it's magic."