We are currently in one of the most tumultuous periods of politics in recent history, and all eyes are on the White House. America’s new oligarchic government is a scary sight to see, and fashion has a bigger impact on politics than you might expect.
Back in 2016 during Trump’s first term in office, many high profile designers who once held a positive relationship with the White House refused to dress First Lady Melania Trump. Designers such as Tom Ford and Marc Jacobs refused to dress the Slovenian native, with Jacobs– an outspoken liberal and supporter of Hillary Clinton–told WWD that he would “rather put [his] energy into helping out those who will be hurt by Trump and his supporters”.
Ford had a more accommodating reason for declining to dress Trump, stating that “even had Hillary won she shouldn’t be wearing my clothes, they’re too expensive” and that “the first lady has to relate to anybody”. However, the tides will most likely shift for Melania Trump’s second go around as First Lady due to Bernard Arnault– LVMH CEO–and his daughter– Christian Dior CEO Delphine Arnault– attended Donald Trump’s second inauguration back in January.
So, will designers still be able to pull memorable looks like they used to, or will they be too steeped in controversy for the actual designs to be noticed? With that said, here are the most memorable moments in FLOTUS fashion history and the fascinating stories behind them.
Dolley Madison: A red velvet gown salvaged from curtains?
Dolley Madison was the wife of number four, James Madison, whose presidency lasted from 1809 to 1817. Dolley Madison is a very underrrated First Lady, basically inventing bipartisan cooperation. Madison, when holding Washington social events, would invite members from both the Republican and Democratic parties, allowing them to socialise.
Madison is ranked among the top six most highly regarded First Ladies for the positive changes she made to the White House, but was she also one of the first upcycling fashion icons?
In 1814, the British attacked Washington, burning the White House to an inhospitable level. But, before fleeing, Dolley managed to grab some White House treasures like the Lansdowne portrait of George Washington, silver, china, and importantly curtains.
Madison managed to save red velvet curtains from the Oval Drawing room (now the Blue Room) before fleeing to Georgetown. Madison had great affection for the drapes, despite the fact that they were not the first choice for the room. Madison died in 1849, and her remaining possessions were sold at an auction a few years later, and in a trunk belonging to Madison, was a red velvet gown.
The collection was donated to the Greensboro Historical Museum, where Madison was born, in the 1960s and the dress was featured in an exhibition in the late 1970s. In an accompanying exhibition book, it was noted that the gown was not made from the lighter velvets normally used for clothing. This was enough for speculation to appear that Madison had in fact repurposed the Drawing Room curtains into a fiery red empire waist gown.
This rumour has never been confirmed to be true as there are no documents linking the dress to a tailor. The dress has also been held under a microscope alongside the curtain fabric, and it couldn’t be confirmed whether it was the same fabric or not. I would like to believe though, that the rumours are true, why else would Madison lug around such a heavy dress in such a distinct fabric and colour? For this alone, Dolley Madison belongs in the FLOTUS fashion hall of fame.
Jackie Kennedy: A pink suit and pillbox hat which none of us will ever see
I think it is safe to say that Jackie Kennedy is probably the most fashionably iconic of the First Ladies. With a tenure marked by multiple personal and political tragedies, Kennedy (later Kennedy-Onassis) was one of the most influential figures in fashion in the early 1960s. Kennedy was the wife of John F. Kennedy, the 35th president from 1961 to his assassination in 1963. Despite being First Lady for a very short time, Jackie made quite the impact in the White House.
Kennedy was frequently featured in fashion magazines, and was named one of the best dressed women in the world in the 1960s. Despite the fact Kennedy’s father was a stockbroker, her mother a socialite, and she literally married into one of the most prominent and rich American families ever, Kennedy’s penchant for expensive French designers drew shock and backlash from the American public.
Inside the White House, Kennedy’s most prominent feat was her dedication to promoting and preserving the White House through an extensive restoration which she oversaw. Kennedy established a fine arts committee to help the project along, and in 1962, hosted the famous televised tour of the White House, which won her an Emmy, making Jackie the only First Lady to ever be awarded one.
Kennedy’s style is just as lauded today as it was 60 years ago, but only one outfit comes to mind when one immediately thinks of Jackie Kennedy, and that is the pink suit and pillbox hat. On 21 November 1963, the Kennedy’s alongside the VP and his wife Lyndon and Lady Bird Johnson, embarked on a political outing to Texas, and this was the first time Jackie joined her husband on such an occasion.
Kennedy wore a bright pink Chanel suit and matching pillbox hat. The suit, despite being a Chanel design, was actually made by New York designer Chez Ninon and copied line for line in order to bypass criticism surrounding Jackie’s preference for French fashion over American. It was actually Jackie’s husband who chose what she wore that day, wanting her to look ‘as marvelous as any of them’, the pink suit being one of his favourites.
As we all know, a short few hours later, the suit would be ruined. Jackie, despite being asked multiple times, refused to take off the suit upon her return to Washington, wanting whomever to ‘see what they have done to Jack’. It was incredibly poignant image for one of the most elegant ladies of the 20th century to appear dishevelled, covered in her husband’s blood.
The suit has become one of the most legendary pieces of clothing in American history that none of us will ever see. The suit is stored in the National Archives, and has never been cleaned. It will not be seen by the public until 2103 according to a deed by Caroline Kennedy, Jackie’s daughter. Even after the 100 year deed expires, the Kennedy’s have the option to re-negotiate for it to never be released.
And the pillbox hat? Most likely, the hat is lost forever. The last person to have had the hat, her personal secretary Mary Gallagher, never disclosed the hats location. It could be sat in the attic of a descendant of Jackie’s personnel, gathering dust, it could’ve been tossed in the bin. One of the most famous ensembles of the 20th century known around the world, also happens to be the one most shrouded in mystery.
Michelle Obama and Jason Wu: A match made in heaven
From Michelle Obama’s oh-so 2009 golden co-ord worn on election day to the outstanding Versace gown Obama wore for her final state dinner, Michelle Obama’s tenure as FLOTUS was marked by many iconic fashion moments which we all watched grow and improve over her husbands 8 year presidency. Obama’s love for expensive designers didn’t plague her tenure as First Lady like it did Jackie Kennedy’s, making her one of the most glamorous First Ladies to date.
During her time in the White House, Obama achieved a lot, most notably her Let’s Move! campaign which took steps to attempt to reverse the obesity crisis in children in America. She created the first White House vegetable garden since the Roosevelt administration and encouraged healthier food choices in schools, supermarkets and an increased focus on physical activity for children.
Michelle and Barack Obama were two of the most consistent supporters of same-sex marriage, and repealing the ‘Don’t Ask Don’t Tell’ policy which barred openly gay, lesbian, or bisexual persons from military service. She is still one of the most popular First Ladies to date due to her approachability, style, and roots, being raised on the South Side of Chicago and later graduating from Princeton University and Harvard Law School.
For both her husbands’ inauguration balls, Obama wore gowns designed by New York based atelier Jason Wu. Of the 2009 dress, Obama said in an interview with WWD in 2010 that ‘it’s simple, it’s elegant and it comes from this brilliant young mind, someone who is living the American dream’ and ‘the countless hours that you can see that he spent sewing this piece made my night even more special’. Obama called the dress a ‘masterpiece’, and accessorised it with Jimmy Choo heels. Clearly, Obama and Wu’s relationship would become a match made in heaven, as Obama chose Wu again for her 2013 gown.
For her second inaugural ball, Obama went for a dramatic, waist-clinching scarlet gown with a low back, which couldn’t be more different from her first dress. Obama clearly understands the power clothes can hold on a famous figure. Pamela Keough, author of Jackie Style, said that ‘when she wore Jason Wu to the first inauguration, he was an absolute unknown, and [she] made his career’ to Vanity Fair.
As the years went by, Obama’s style got sleeker and sleeker, with a personal favourite being the outstanding monochromatic burgundy ensemble by Sergio Hudson worn to the 2021 Biden inauguration, with Obama even matching her Covid preventing face-mask with leather black gloves and boots.
Post First Lady-dom, Obama has been embracing her black heritage in a way she felt not possible as the most famous woman in America given how ruthless the American media can be. On her 2022 book tour, Obama wore her hair in curly up-do’s, braids and braided high ponytails and has continued to do so since.
Melania Trump: the ‘I really don’t care, do u?’ coat which sparked outrage
Heading back into the White House for the second time, all eyes will be on Melania Trump’s style choices, which were often hotly contested during her first run as FLOTUS. Trump’s 2016 Tiffany blue inauguration dress by Ralph Lauren was very The Handmaid’s Tale-esque, and her 2025 ensemble’s hotly debated wide brimmed hat had rumours flying that she simply wore it as she didn’t want Trump’s mouth anywhere near hers.
In 2018 on a trip to a migrant child detention centre in Texas, Trump made a very questionable fashion choice en route. Instead of a demure, somber outfit, Trump wore a $39 khaki jacket from Zara emblazoned with the words ‘I really don’t care, do u?’ on the back. At the time, Melania’s spokespeople insisted there was no hidden message in the jacket, and she simply wore it on and off the plane, but later in an interview with ABC, Melania declared there was indeed an intention behind it.
Trump declared that the jacket “was for the people and for the left-wing media who are criticising me. I want to show them I don’t care. You could criticise whatever you want. But it will not stop me to do what I feel is right”. Despite Melania’s rationalisation behind the choice, it is still debatable whether a trip to a child immigrant detention centre is the time to make a statement.
Going to a border where, under her husband’s administration, children were being held and families ripped apart, didn’t exactly feel like the time or place to take a stand. An act which could have been seen as caring and sympathetic was immediately undercut by a callous fashion choice.
Nancy Reagan: The iconography of ‘Reagan red’
Colours can often define the tenure’s of First Ladies. For Jackie Kennedy it was pink, for Lady Bird Johnson it was yellow. But, no colour was more iconic to a FLOTUS than red was for Nancy Reagan. Reagan and red were a match made in heaven–literally, Reagan was also buried in red. Often overlooked, Nancy Reagan was one of the most fashionable ladies in the 1980s, epitomising the periods over the top prints and structures in a signature crimson.
By sticking to her signature colour, Reagan became a style icon as her husband transformed the landscape of the US. Reagan had a size two waist and loved to show it off, ‘I like red,’ she once said according to Town and Country magazine, ‘it’s a picker-upper.’ Whether she was entertaining Mr T or Princess Diana, Reagan was in red.
During her time as First Lady, Reagan sought private donations to completely renovate the living quarters of the White House as well as rooms adjacent to the Oval Office. Many of the changes Reagan made to the White House still stand today, despite some of the renovations receiving criticism for being funded indirectly by the tax-paying public as they were somewhat funded by tax-deductible donations.
In 1982, Reagan launced the infamous Just Say No drug awareness campaign, which became her major initiative as First Lady. Reagan was very involved in the campaign, travelling across America visiting rehabilitation and prevention centres. She appeared in the music video for Stop the Madness, a 1985 Just Say No endorsed music video starring names like Whitney Houston, Arnold Schwarzenegger and La Toya Jackson. In 1988 she was the first First Lady invited to address the United Nations General Assembly where she she spoke on international drug and trafficking laws.
Despite this, Reagan was most known for her lavish style, with her inaugural wardrobe believing to have cost upwards of $25,000. Her elegant and lavish fashion was often hailed as the epitome of glamour, but was also steeped in controversy. In 1982, Reagan revealed that she accepted thousands of dollars in clothing and jewellery, defending her actions by stating that she was promoting the American fashion industry. Regardless, to be so associated with a shade of red to have it named after you, makes Nancy Reagan a FLOTUS fashion icon.
FLOTUS fashion has always been a fascinating mix of personal style, political messaging, and cultural influence. From bold statements to subtle symbolism, each FLOTUS has used fashion to leave her mark. Whether intentional or not, their outfits have sparked conversations that go far beyond the clothes themselves—proving that in the world of politics, even a dress can make history.
