Hillary Clinton's Chicest First Lady Style Moments

Long before Kaitlan Collins proved she was the queen of the pantsuit, there was Hillary Clinton. Both during her time as First Lady and afterward, especially when she was running for U.S. president, Clinton very much leaned into pantsuits. So much so that in 2016, a Facebook group of her supporters named themselves Pantsuit Nation.

"It's interesting that someone who has had the least regard of fashion has been a pioneer in some ways," director of the four-part documentary, "Hillary," Nanette Burstein told Marie Claire in March 2020, explaining that Clinton wanted a uniform to make things simpler. "As a result of doing that, it created a cultural shift," Burstein told the magazine, adding that while Clinton isn't the first or the last woman in politics to wear pantsuits, she's definitely the first to make it her go-to look.

But before Clinton made pantsuits her uniform, she had some very chic First Lady style moments. Looks that have become so iconic that to this day, people still talk about them. While the current First Lady, Melania Trump, has worn a whole slew of outfits that totally missed the mark, the same can't be said for Clinton. And considering she was First Lady for the bulk of the 1990s, an era not exactly known for sophisticated fashion looks, that's really saying something about Hillary's attention to style details.

Although not quite a houndstooth pattern, Hillary Clinton's red and black plaid jacket is the epitome of 1990s chic — as is the matching thick red headband, a hair accessory that Clinton wore a lot throughout the decade. In 1992, Bill Clinton's presidential campaign stopped in New Hampshire, allowing for a deep-in-thought photo of Hillary to be taken, looking cool and relaxed. Clinton is only 45 years old here and has no idea what's about to unfold for her. Or maybe she does — her eyes do have a distinct look of ambition and determination.

While some people, like Kimberly Guilfoyle, used the inauguration as the opportunity to wear their most questionable looks to date, others have demonstrated that they absolutely understood the assignment. When Hillary Clinton took the stage to dance with Bill Clinton at the Inaugural Ball, she proved she knew exactly what she was doing with her violet lace and beaded gown designed by Sarah Phillips. Not only was the dress stunning, literally stealing Bill's moment, but in choosing violet, the color of bipartisanship, Clinton sent a message to everyone watching that night.

For the 1993 National Governors Association winter meeting, Hillary Clinton wore a black Donna Karan dress that had many people clutching their pearls in horror. Not only is Clinton bearing her shoulders — gasp! — but even the Getty photograph description points out that the flash of the camera made Clinton's underwear visible. In September 2015, Clinton was interviewed for Lena Dunham's now-defunct Lenny Letter, and this particular dress came up. "This is what's called a cold-shoulder dress ... And like everything I do, it turned out to be controversial," Clinton told Dunham, via Time. "I'm hardly a fashion icon."

As First Lady, Hillary Clinton wore a lot of red. According to color psychology, red stimulates thoughts of power, success, and ambition, so the fact that Clinton wore so much red makes a lot of sense. After all, this was not a woman who planned to stop her political career as First Lady. While hosting a meeting in the White House Rose Garden (RIP) for the League of Women Voters, Clinton wore a bright red power suit, which was an ideal choice for the event.

In 1994, the President and First Lady hosted Empress Michiko and her husband, Emperor Akihito of Japan, at the White House. We may not have royalty in the U.S., but during the welcoming ceremony on the South Lawn, Hillary Clinton looked just the right amount of stately in her butter yellow suit, wide-brim hat, and a single strand of pearls around her neck. Although butter yellow would become the new neutral in 2023, back in 1994, there's a good chance that Clinton chose to wear this color because it's associated with happiness and warmth, making it an ideal shade to wear when welcoming the visiting Japanese royals.

For the 75^th anniversary of women gaining the right to vote, both Hillary and Bill Clinton celebrated in Wyoming. Based on throwback photos that Hillary posted on Instagram, the two apparently did a little camping in Jackson Hole while they were out there. But when she wasn't huddled over a campfire with Bill, Clinton totally nailed the western look of Wyoming with this long beige dress, a hat to protect her from the sun at that elevation above sea level, and, of course, cowboy boots.

In 1997, Hillary Clinton won something not every First Lady gets nominated for, let alone wins: a Grammy award. Clinton won the award for the Best Spoken Word or Non-Musical Album for her audio version of her 1996 book, "It Takes a Village: And Other Lessons Children Teach Us." For the big night, Clinton wore a full-length and long-sleeve gown by Oscar de la Renta. The gold lace top was paired with an olive taffeta skirt, making it one of her most elegant looks from her First Lady era. Clinton's hair was also noticeably shorter than it had been, having opted for a chin-length haircut for a bold new look, which she styled with side-swept bangs.

Although by this point in her marriage to Bill Clinton, there had been fidelity, then lies about there not being fidelity, and he was impeached on December 19, 1998, Hillary Clinton never left his side. Considering she had her own political aspirations — she ran for U.S. Senate less than two years later in 2000, and won — it was likely a strategic move on her part. On December 31, 2024, Clinton posted a throwback photo on Instagram from NYE 1999 of her and her family. While the smile looks a bit forced, Clinton's black dress, wide silver choker, and hair are spot on.

When Hillary Clinton attended TNT's "A Very Special Christmas" concert celebrating the Special Olympics in December 2000, she was a vision. Not only were her hair and makeup impeccable, but the blue leafy design around the neck of her black dress did her so many favors — she was literally glowing. To complete her outfit, she wore a gorgeous diamond necklace that elevated the look even more. Considering she'd been elected U.S. Senator just the month before and would be taking office in January 2001, Clinton clearly had lots to smile about and celebrate that night.

To prove that Hillary Clinton can do casual just as chicly as she can dress to the nines, she was captured getting out of a limousine so she could board Air Force One on a cold and blustery day in January. Clinton and her family were heading to their home in Chappaqua, New York, and despite just wearing a champagne-colored winter jacket and a pretty standard red plaid scarf, the sunglasses say it all: I've only got one more year of this First Lady thing, then I'm on to bigger and better.