13 Most Daring Outfits First Ladies Have Worn

Who Wore Boldness Best? First Lady Fashion Highlights

When we think about America’s First Ladies, we also think about influential icons who have used their platforms to express individuality, redefine societal norms, and inspire generations. Each First Lady brought her unique flair to the White House wardrobe, leaving a mark on American fashion.

Let’s discover together 13 daring outfits worn by the American First Ladies.

1. Frances Cleveland – wore dresses that showed her shoulders

Grover and Frances Cleveland married in 1886 and became the first president and lady who wed in the White House. Frances Cleveland was the youngest first lady in history, just 21 years old, but it didn’t stop her from becoming a real fashion icon.

She used to wear unique dressed that showed her shoulders and it was a bold fashion choice back in the 1880s. It’s interesting how, at that time, even though there were a lot of critics Frances Cleveland just listened to her hard and continued to amaze everyone with her courage and style. Was it a dangerous game she played? Totally, yes. But… was it worth it? Tell us your ideas in the comment section found below.

2. Betty Ford – was photographed in pants

There is only one time when Betty Ford was photographed in pants. She was dancing on her last day as a first lady in 1977. Oh, I almost forgot to mention that she was dancing on the table in the Cabinet Room! The photography became famous worldwide and represents one of the most iconic fashion moments in history.

Even though Betty Ford was posing and trying to support the women’s liberation movement of the 1970s, her outfit choices were still criticized by the National First Ladies Library. It was unacceptable for a first lady to be seen wearing pants.

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3. Jacqueline Kennedy – wore pink pants

In the 1960s it was considered “shocking” that Jacqueline Kennedy wore pink pants. Even though nowadays it doesn’t seem a huge fashion mistake, back in time, wearing pants and especially really bright colors, was not considered normal for the first ladies. They always needed to follow the fashion rules and be extremely careful with their appearances. Such outfits could have made her and her husband lose some votes. That’s how bad it was.

“This fall the question of style for a President’s wife may be a Great Issue. Can too much chic – or too little – mean votes?” Martha Weinman of The New York Times wrote.

4. Nancy Reagan – wore a one-shoulder dress

Back in 1981, Nancy Reagan’s choice of a one-shoulder inaugural gown was seen as a daring outfit. Robin Givhan, a senior critic from The Washington Post, said in 2016 that it was surprisingly bare for a first lady to show up like that. Nancy Reagan received a lot of criticism, even though the dress wasn’t a basic choice. It was made of lace over silk satin and designed by James Galanos.

5. Michelle Obama – wore a dress with a halter neckline and open-back

Michelle Obama made a fashion mistake at the inaugural ball gown in 2013. She wore a spectacular red dress, designed by Jason Wu, but it was considered daring. A first lady shouldn’t wear open-back dresses that reveal too much of their body. We live in a world where fashion is always changing and it feels like the rules are less and less strict, but not for the first ladies. They still need to pay attention to their appearances, to avoid criticism. As we all know, criticism can ruin a political figure’s image and career, so these kinds of outfit mistakes shouldn’t be made.

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6. Michele Obama – wore a sleeveless black dress

Michele Obama’s arms were making headlines, right after she wore a sleeveless aubergine dress for her official White House photo. Even though the first lady looked very decent and incredibly stunning, there was still a lot of criticism going on. Michele Obama wrote about this moment, considered a fashion incident, in her book called “Becoming”. So, in case you want to find out more about her, we totally recommend you purchase the book from Amazon if you haven’t already read it.

7. Michele Obama – wore a showstopping rose-gold dress

At her final state dinner in 2016, when the presidential couple was welcoming Italian Prime Minister Matteo Renzi and his wife, Agnese Landini, Obama chose to wear a showstopping rose-gold dress made of chain mail. The clothing item was considered inappropriate for the White House meeting, despite being designed by the Italian fashion house Atelier Versace.

8. Melania Trump – wore a too-expensive Dolce & Gabbana jacket

The first lady appeared at a summit in Italy in 2017 with a spectacular jacket with a lot of unique floral appliques. She was attending the Group of Seven summit and her outfit choice was harshly criticized. The full cost of the jacket was more than most Americans make in a year, so the controversial choice has attracted much criticism.

How the First Lady looked on that day was breathtaking. She added her final signature to the look by wearing her famous sunglasses. But, unfortunately, her beauty didn’t help her escape from the embarrassing situation.

9. Melania Trump – wore a hot-pink dress with voluminous sleeves

According to Insider’s Kate Taylor, Trump’s fashion choice for a 2017 speech at the UN indicated her lack of public speaking. Melania Trump wore a hot-pink Delpozo dress with voluminous sleeves which was considered a big mistake by fashion critics. She should have chosen something way more elegant and simple. The dress looked oversized behind a podium.

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10. Melania Trump – “I really don’t care. Do u?” Zara jacket

Probably one of the most notorious fashion moments made by Melania Trump, was when she wore a Zara jacket with a message that was considered totally inappropriate and judged by lots of Americans. The First Lasy wore the jacket with this controversial message when she visited immigrant children at a government facility in 2018.

Later, in an ABC News interview, she said the message was meant for the people who constantly criticize her. She has been feeling overwhelmed by all the critics, she even said that it seemed like she was the most hated person in the world.

11. Melania Trump – wore a hat that stole the show

In 2018, Melania Trump was welcoming French President Emmanuel Macron to the White House. The First Lady was wearing a big white hat that matched her white belted suit by Michal Kors. Even though it wasn’t considered a huge fashion mistake, it wasn’t considered one of her best outfit choices.

12. Jill Biden – wore black patterned tights

The black patterned tights the First Lady wore in 2021, became known as “Fishnetgate”. Jill Biden was previously wearing the tights in May 2016 and her outfit was considered too risky.

In 2021, after a lot of criticism, Biden responded in an interview with Vogue. She said that she was amazed at how much people pay attention to every little detail. She also made sure to clarify that they weren’t lace or fishnets, the tights were very pretty stockings.

13. Jill Biden – wore a glittering dress that showed her shoulders

At the 2023 Grammys, Jill Biden went on the stage to present the award for an Iranian singer and songwriter. Shervin Hajipor won the award for Best Song for Social Change for her protest anthem “Baraye”. The First Lady also presented the Best Song award which went to  Bonnie Raitt’s “Just Like That.”

The glittering custom Oscar de la Renta gown was not seen as a wise choice for the event. The glitter couldn’t make the critics not to observe Jill Biden’s shoulders.

Before leaving, tell us about your opinion. Who wore it best? Are the waves of criticism too harsh? Or should the American First Ladies pay more attention to what they wear?

Considering the 2024 Presidential Election results, you may want to read more about our First Lady, Melania Trump. Here is a great article that can be found on our website: 5 Melania Trump Facts Revealed in Tell-All Book.

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