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First Lady fashion ranked: From Jacqueline Kennedy to Michelle Obama

Whose White House wardrobe comes out on top? We delve into the sartorial archives of history's fabulous First Ladies

Tania Leslau
Fashion features writer
November 5, 2024
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First Ladies and their wardrobes are pure dynasties unto themselves. Each one commands a look that tells us precisely who they are, or at least who they want us to think they are. 

Jaqueline Kennedy, for instance, didn’t merely enter the room; she glided in as if escorted by a parade of pastel-coloured suits and pillbox hats. She gave American fashion its own grace note, creating a uniform that felt equal parts Audrey Hepburn and royal.

Then there’s Nancy Reagan, who had her ‘Red’ phase, turning the hue into a declaration of power. Nancy didn't do soft; she did statement, and her wardrobe was practically a Dior-sponsored event. 

 Former First Lady Jacqueline Kennedy enjoys herself at a picnic circa the 1960s.  © Getty
Former First Lady Jacqueline Kennedy in the 1960s

Fast-forward to Michelle Obama, the champion of sleeveless sophistication. Her J. Crew-meets-Jason Wu style was part invitation, part power move, showing us that style and substance can tango to create a powerful yet personable facade. Melania Trump’s icy elegance felt almost cinematic, as if she stepped out of a high-fashion noir film. 

Each First Lady’s wardrobe reflects the political zeitgeist. They’re icons not just of fashion, but of how fashion frames power.

First Lady Claudia 'Lady Bird' Johnson in 1965© Getty
First Lady Claudia 'Lady Bird' Johnson in 1965

So, considering the current, not to mention, intensely heated political Presidential Campaigns of Donald Trump and Kamala Harris, what better opportunity to dissect the archives of these fashionable First Ladies?

We ranked the fashion of history’s First Ladies who debuted distinct yet ever-eye-catching looks. Please note, all opinions are my own and I am easily swayed by early 20th century ruffles. 

History's most stylish First Ladies:

10. Melania Trump 

2017-2021

2017-2021

Unlike several of her husband's policies, Melania Trumps' style is solid. Her style is defined by a polished, often minimalistic elegance that combines luxury and high fashion with a distinctly European sensibility. 

Sleek, tailored silhouettes and neutral colour palettes are her go-to, frequently peppered by bold structured pieces. She's championed designs by a variety of high-end designers like Dolce & Gabbana, Hervé Pierre, Dior, and Ralph Lauren, culminating in a safe but structured wardrobe spanning trench coats to tailored suits and dramatic evening gowns.

Her most notable outfit came back in the summer of 2018, when the then-First Lady visited a migrant child detention centre in Texas. Her outfit choice sparked media sensation - with the 54-year-old sporting a $39 Zara jacket emblazoned with the phrase: ""I really don't care, do you?"

9. Eleanor Roosevelt

1933-1945

1933-1945

Eleanor Roosevelt is remembered as a trailblazing First Lady, human rights advocate, and champion for social justice. She transformed the role, promoting civil rights, women's empowerment, and global humanitarian work. Known for her activism, she later helped draft the Universal Declaration of Human Rights, cementing her legacy in American and world history.

Her fashion was practical, modest, and understated, reflecting her dedication to public service over style trends. Unlike more overtly glamorous First Ladies, Eleanor favoured simple, conservative silhouettes with long skirts, tailored jackets, and modest necklines, often accessorised with pearls or a brooch. Her wardrobe was functional, suited to the busy life of a working First Lady deeply involved in activism. While she rarely sought to make fashion statements, her look conveyed an image of approachability and sincerity. Yet, on formal occasions, she embraced elegant evening gowns that balanced her understated style with the dignity her position required.

8. Jill Biden

2021-Today

2021-Today

Dr. Jill Biden, the current First Lady of the United States, is known for her commitment to education, military families, and cancer research advocacy. A lifelong educator, she continues to teach English at a community college - a historic first for a sitting First Lady. Her support for military families and cancer awareness, often through initiatives like Joining Forces and the Biden Cancer Initiative, reflects her deep sense of service and empathy.

Her fashion style is polished yet accessible, frequently featuring vibrant colours, bold patterns, and a mix of American and international designers such as Brandon Maxwell, Gabriela Hearst, and Markarian. Known for embracing florals and classic silhouettes, she exudes warmth and professionalism. She often wears dresses with sleeves, tailored jackets, and midi skirts, crafting an image that’s both sophisticated and approachable. 

7. Hilary Clinton 

1993-2001

1993-2001

Hillary Clinton is marked by her extensive political career and dedication to public service. She served as First Lady, U.S. Senator, Secretary of State, and was the first woman to secure a major party’s presidential nomination. Known for her advocacy on healthcare, women’s rights, and children’s issues, she’s a key figure in American politics.

Her wardrobe reflects a focus on power and practicality, often centred on her iconic suits, which have become a defining feature of her style. She frequently wears suits from American designers like Ralph Lauren and Michael Kors, symbolising her dedication to country. Throughout her career, she’s also been seen in pieces by Oscar de la Renta, whose classic designs aligned with her formal appearances as First Lady and Secretary of State.

In recent years, she’s embraced brighter hues and prints, using designers like Giorgio Armani and Escada to convey a refined, professional look. Her love for sunset hues from orange to yellow brought a freshness to First Lady fashion, which didn't go unnoticed

6. Mamie Eisenhower 

1953-1961

1953-1961

Scoring a modest sixth place is none other than Mamie Eisenhower. A highly popular First Lady and wife of President Dwight D. Eisenhower, Mamie is remembered for her charm, vibrant personality, and her signature style marked by pink dresses and pearls. As First Lady, she brought warmth to the White House, popularised the colour 'Mamie Pink,' and was known for her dedication to hospitality and entertaining.

She embraced a traditional, ladylike style that reflected 1950s America, favouring polished ensembles with a touch of opulence. Her look emphasised charm, warmth, and the ideal of domestic elegance. She frequently wore matching gloves and hats, creating a refined, ladylike image. Mamie’s style was highly feminine, making her a popular First Lady who represented the era's domestic ideals and American glamour. Plus, the polka dots? So 2024.

5. Nancy Reagan

1981-1989

1981-1989

Nancy Reagan is known for her influential role as First Lady from 1981 to 1989, particularly her advocacy for the 'Just Say No' drug awareness campaign and her commitment to promoting a positive image for the White House. She was a devoted partner to her husband, President Ronald Reagan, and played a key role in shaping his administration's public relations. Her efforts in restoring the White House and hosting lavish social events are also notable aspects of her legacy.

Nancy's style was characterised by its classic elegance and sophistication. Her wardrobe was perfectly pappered with playful pieces, spanning rose print to metallics and polka dots. She loved her designer labels, notably wearing iconic pieces from Oscar de la Renta and Chanel. The former First Lady's signature look included tailored suits, elegant evening gowns, and bold accessories like statement jewellery. Timeless and fun, Mrs Reagan's fashion taste added a personality-fuelled spin on classic First Lady fashion.

4. Michelle Obama 

2009-2017

2009-2017

Effervescent in personality and widely beloved, Michelle Obama is one of the most celebrated First Ladies. She embraced the role from 2009 to 2017, where she focused on initiatives related to health, education, and military families. Barack Obama’s wife platformed the ‘Let's Move!’ campaign to combat childhood obesity, promoted healthy eating through the White House garden, and advocated for education through the ‘Reach Higher’ initiative. She’s also known for her persuasive writing (as evidenced by her memoir Becoming) public speaking and ability to connect with diverse audiences, becoming a role model for women and girls worldwide.

Her fashion style is distinctive and influential, blending high-end designers with accessible brands. She often wore pieces by Jason Wu, who designed her inaugural gown, alongside American labels like J. Crew and Narciso Rodriguez. Michelle embraced vibrant colours, eye-catching patterns, and modern silhouettes, reflecting her personality and confidence. Her wardrobe choices not only showcased her love for fashion but also made statements about body positivity and self-expression, solidifying her status as a modern style icon.

3. Claudia 'Lady Bird' Johnson 

1963–1969

1963–1969

Sit back down Gen Z because Lady Bird Johnson pipped butter yellow as the It-hue long before TikTok. The wife of President Lyndon B. Johnson is known for her significant contributions to environmental conservation and beautification efforts during her time as First Lady from 1963 to 1969, making her sartorially and environmentally in the know.

Her fashion style was characterised by grace and simplicity, favouring classic silhouettes and soft, warm tones  that reflected her Southern roots. Lady Bird often wore tailored dresses, elegant coats, and stylish hats, embodying the polished, sophisticated aesthetic of the 1960s. She was known for her love of floral prints, which aligned with her commitment to environmental beautification. A lady who loved a theme. 

2. Betty Ford

1974-1977

1974-1977

Greens, golds and girlish prints, Betty Ford's wardrobe never knew a dull moment. The wife of President Gerald Ford is remembered for her advocacy on women's health issues and her candid discussions about addiction and mental health. As First Lady from 1974 to 1977, she founded the Betty Ford Center in 1982, providing treatment for substance abuse, and became a prominent figure in the fight for women's rights, including breast cancer awareness and the Equal Rights Amendment. Her openness about her own struggles with addiction and health challenges helped destigmatise these issues, making her a respected advocate for social change. Très chic.

As for her style, she had a penchant for suits, longline dresses, and stand-out accessories, reflecting a sophisticated yet approachable aesthetic. Her love of vibrant palettes and pretty prints was evident -  which she pairedf with hr signature short hairstyle, making her a style icon of her era.

1. Jacqueline Kennedy

1961-1963

1961-1963

You knew this was coming. Jacqueline Kennedy, the First Lady of the United States from 1961 to 1963, is globally celebrated for her timeless elegance, grace, and impactful contributions to American culture. Her style, characterised by chic tailored suits, pillbox hats, and signature sunglasses, redefined First Lady fashion, influencing trends for decades. She often wore iconic designs by renowned designers such as Chanel and Oleg Cassini, bringing high fashion into the White House and elevating the national perception of style.

Beyond fashion, Jackie’s legacy endures in pop culture through her image as an icon of sophistication and resilience. Her role in the arts and support for the Kennedy Center for the Performing Arts further solidified her influence on American culture. Documentaries, films, and television portrayals continue to explore her life, emphasising her enduring impact on fashion and her role in shaping the public's fascination with the Kennedy family. Jackie remains a symbol of elegance and strength in the collective American memory.

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