Hillary Clinton's Jaw-Dropping First Lady Fashion Moments Put Melania Trump To Shame

By Camille Terrania
Democratic presidential debate features candidate former Secretary of State and U.S. Senator Hillary Clinton at Wynn Las Vegas in first CNN Democratic Debate on October 13, 2015 (2015) Joseph Sohm/Shutterstock

The fashion of first ladies has captured and held the interest of the public since the dawn of the U.S. government — literally. George Washington's wife Martha Washington, the first woman to ever take on the role, did not have her every outfit photographed and commented on by people all over the world, but she was still so overwhelmed by the attention her wardrobe received that she avoided stepping out of her home. More than two centuries later, the 18th-century dresses have been replaced by skirt suits, but the public's fascination with the looks of presidential spouses is stronger than ever. However, many modern first ladies, including Hillary Clinton, used this attention to their advantage and made fashion a tool and platform to send a message, boost a cause, or promote American designers. 

In the case of Clinton, while she's not usually the first to come to mind when we think of first lady fashionistas, she can't be left out of the conversation about political style icons. Like Jacqueline Kennedy Onassis, she has her own trademark style: the pantsuit. She became the first presidential spouse to rock a pantsuit in her official first lady portrait, resulting in one of the most scandalous first lady outfits ever worn, and later made it her uniform during her time as senator and presidential candidate, turning it into a symbol of gender equality. However, there was a time when Clinton's wardrobe wasn't exclusively filled with pantsuits of every color of the rainbow. In fact, she could give Melania Trump, who served up some of her absolute best fashion moments ever during her first term in the White House, a run for her money when it came to first lady wardrobes. 

She rocked two black and red outfits with very different vibes in 1992

Hillary Clinton smiles during her husband Bill Clinton's presidential campaign for the Democratic nomination in New Hampshire (1992) Rick Maiman/Getty Images

Headbands were a staple of Hillary Clinton's looks throughout her husband Bill Clinton's campaign and her time as first lady, and she made them work with various types of outfits. If we're talking in Taylor Swift terms, she gave "Folklore" in this red and black plaid cardigan, red turtleneck sweater, and matching headband (pictured above) that she donned in 1992. However, in the same year, she seemingly entered her "Reputation" era when she paired the same headband with a red turtleneck, oversized black leather jacket, short black skirt, and matching black boots.

Hillary gave royalty in this houndstooth look

First Lady Hillary Rodham Clinton smiles in Washington, D.C. (1997) Mark Reinstein/Getty Images

By 1997, Hillary Clinton was already in her second term as first lady and knew the ropes of the position. This seemed to be reflected in this effortlessly chic 1997 look comprising a black and white houndstooth jacket and a black roll-neck turtleneck sweater. She completed the look with pearl earrings and a necklace with a cameo pendant, both of which were consistent with her preference for large accessories but didn' take away from the elegance of her outfit. This look reminded us of Princess Diana's iconic houndstooth outfits, including this ensemble from 1987.

Hillary outshined her husband at his own inaugural ball in this incredible gown

Bill and Hillary Clinton stand on stage January 20, 1993 in Washington, DC. Eleven inaugural balls were held on the same evening in honor of President Clinton's election (1993) Porter Gifford/retired/Getty Images

Speaking of regal, Hillary Clinton was the belle of the inaugural ball in this violet gown that she wore on the day her husband Bill Clinton took his oath as the 42nd president in 1993. Hillary looked like she was wearing the night sky on her body, outshining Bill as she danced with the then-president on stage at the inaugural balls held in his honor. However, the jaw-dropping outfit came with an equally jaw-dropping price, $50,000, making it one of the most expensive first lady outfits ever.

She wore practically every shade of pink

Hillary Clinton, Al Gore, and Tipper Gore attend Nelson Mandela's Inauguration (1994) David Turnley/Getty Images

Hillary Clinton loved a good pink moment, and she wasn't picky with the shade. Sometimes, it was just a pop of color in an outfit. For example, light pink lapels and cuffs added a feminine touch to the suit she wore (pictured above) to Nelson Mandela's 1994 inauguration, while a top in a darker shade of pink brought out the pink in a houndstooth skirt suit (third photo below). Other times, pink was the star of the show, like in her bold, all-hot pink suit and demure salmon pink outfit (pictured below).

Hillary's monochromatic outfits stood the test of time

President Bill Clinton, First Lady Hillary Rodham Clinton, Vice President Al Gore, and Second Lady Tipper Gore smile as they make their way to a health care reform event on the south lawn of the White House (1993) Cynthia Johnson/Getty Images

Hillary Clinton wore one of her most flattering first lady looks ever to a White House event in 1993.The jacket, dress, and belt all came in a rich royal blue that perfectly complemented her skin tone and hair, and featured gold detailing. Two years later, she went full Barbie in a blush pink set that she accessorized with gold and pearl jewelry and a pair of glasses with red frames. While they had hallmarks of '80s and '90s fashion, we could totally see another first lady rocking these today.

Hillary stole the spotlight at the 1993 Kennedy Center Honors in a festive burgundy number

Hillary Clinton attends the Kennedy Center Awards at the White House (1993) Jeffrey Markowitz/Getty Images

If Nancy Reagan owned the bright Reagan Red, then burgundy belonged to Hillary Clinton after she wore this stunning velvet gown by Oscar de la Renta in December 1993. The festive dress, which she donned for the Kennedy Center Honors, featured a figure-hugging bodice and a full, flared skirt and was paired with large gold earrings and a three-strand pearl-and-gold necklace. The red lip was the perfect finishing touch for the elegant look.

Hillary was radiant in one of her last first lady looks

President Clinton poses with former Presidents George Bush, Gerald Ford and Jimmy Carter and first ladies, past and present, Barbara Bush, Lady Bird Johnson, Hillary Rodham Clinton, Betty Ford and Rosalynn Carter (L-R) in the State Dining Room of the White House, November 9, 2000 (2000) Michael Smith/Getty Images

As a disastrous second term marked by her husband Bill Clinton's affair scandal with Monica Lewinsky and subsequent impeachment drew to a close, Hillary Clinton decided to go out with a bang fashion-wise during one of her last major events as first lady. She donned a regal gold gown when she and Bill attended a dinner celebrating the 200th Anniversary of the White House alongside past presidents and first ladies in November 2000.

Hillary brought her pantsuit A-game to Paris

Hillary Clinton smiles as she arrives in Paris (1994) Langevin Jacques/Getty Images

Hillary Clinton stepped out in one of her most stylish pantsuit looks ever while visiting Paris in 1994. She stunned in a fitted jacket that showed off her snatched waist, wide-leg trousers, and a pair of black heels. Aside from the use of different textures to level up the monochromatic outfit, another interesting part of her look was her special accessory: a clutch that looked smaller than her hand and resembled a black-and-white cat. Designed by Judith Lieber, the bag was created in honor of her and Bill Clinton's beloved pet cat, Socks.

Hillary dressed like royalty to meet royalty in 1994

First Lady Hillary Rodham Clinton and Empress Michiko of Japan stand on the South Lawn of the White House as they watch the official welcoming ceremony on June 13, 1994 in Washington, DC (1994) mark reinstein/Shutterstock

Hillary Clinton looked ready for the Royal Ascot in a yellow skirt suit, blouse, and hat during a 1994 state visit. Paired with pearl jewelry, white gloves, and white pumps, the outfit seemed like something you'd find in Queen Elizabeth II's closet, which made sense considering she and Bill Clinton welcomed Emperor Akihito and Empress Michiko of Japan to the White House at the time. Hillary's look received thumbs up all around from social media users, with one writing on X (formerly Twitter): "This look was a serve. Top tier."

Hillary's off-duty looks sometimes topped the ones she wore on the clock

Hillary Clinton sits on a chair as she enjoys a vacation with her family in Wyoming in August 1995 (1995) @hillaryclinton/Instagram

Hillary Clinton enjoyed a vacation with Bill Clinton and their daughter Chelsea in Wyoming in August 1995, but she didn't take a break from serving looks. In 2021, Hillary shared a throwback photo from that vacation showing her rocking an outfit that defined Western elegance: a belted maxi dress, cowboy boots, a cowboy hat, sunglasses, and maximalist jewelry. The snap not only reminded us she's always been out of Bill's league but also showed us one of many old-school first lady outfits that should make a comeback.

Recommended