Michelle Obama Fashion: Top 10 Best-Dressed First Ladies

Michelle Obama's daring fashion choices may ignite debate—but they also bring style back to the White House. Kate Betts on the 10 best-dressed first ladies of all time.

Best dressed first ladies.

In the frenzy of award-ceremony season, instead of musing on the dos and don’ts of Hollywood’s red carpet, let’s take a look back at one of history’s most-discussed best-dressed list: that of first ladies over the course of this nation’s history. One first lady brought a radio to the White House (Grace Coolidge), while another brought her own sewing machine (Rosalynn Carter), all of the following first ladies brought a unique—and often emulated—sense of style.

Gallery: Top 10 Best-Dressed First Ladies

Michelle Obama has certainly done her part to hold up the tradition of White House style, but she isn’t the first first lady to generate controversy with her gowns and accessories. Star Trek belt? Sure, but Martha Washington had her “queen’s nightcap” and Dolley Madison had her wacky turbans. Madison, who was by all accounts perhaps one of the top four best-dressed first ladies and certainly one of the most beloved, was famous for outfits that would have received major side-eye from Joan Rivers. Not satisfied with the New World styles, Madison made a concerted effort to evoke European trends by using more recherché fabrics and doing crazy Issy Blow-type things such as tying turbans on her head and sticking peacock feathers in them.

The young and beautiful Julia Tyler—also known as the Rose of Long Island—took her cues from Dolley, beguiling her fans with her beauty and earning the nickname “Lovely, Lady Presidentress” by acting like a queen, sashaying around Washington trailed by ladies-in-waiting. She mimicked Dolley’s penchant for headgear, wearing satin headdresses embroidered with feathers and diamonds. If style is about more than just what one is wearing, and I think it is, then Tyler made her real mark on the position by dancing the polka in the East Room—a first.

Then there was Mary Todd Lincoln, a veritable shopaholic. People tend to remember her splurging at Lord & Taylor in New York City, the endless yards of costly fabric, and her later years when profligacy left her destitute. As first lady, and as an outsider in Washington, she blamed her extravagance—giant hoopskirts and rosette-strewn gowns—on what she felt was a tremendous pressure to fit in.

Francis Cleveland, known as Frankie in the press, was the first “It Girl” first lady. Married to the bachelor President Grover Cleveland at only 21, Frankie wore a white satin wedding gown with a 15-foot train and wrapped her hair in a low knot on the back of her shaved neck, a style that became known as “La Cleveland” and was copied by women around the country. Edith Roosevelt wore couture dresses designed by Monsieur Worth in Paris, but she didn’t have the public personality to land on a best-dressed list. That honor went to her stepdaughter, Alice Roosevelt, who became the center of press attention and public scrutiny and an icon to women around the world.

Grace Coolidge’s staff nicknamed her “Sunshine” because she had such a joyful attitude about living in the White House. She wore brightly colored flapper dresses, typed her own letters, and often had her picture taken with visitors in front of the North Portico. Every accessory she embraced, from cloche hats to sparkled belts, resurfaced in the women’s pages of newspapers. And when she posed for her White House portrait by Howard Chandler Christy in a red sleeveless dress, the color became all the rage.

Pink was Mamie Eisenhower’s favorite color, so much so that she had her bedroom at the White House entirely redecorated in it, including the wastepaper baskets. And although Mamie was more matronly than many of the first ladies who followed her, she makes the list because she was the quintessential '50s housewife: Her look of wasp-waisted dresses, matching pocket books, shoes, and hats set the tone during her tenure at the White House.

Of course no first lady captured the cultural zeitgeist with her style quite the way Jackie Kennedy did. Thanks to the advent of color television, her love of rich fabrics such as duchess satin and shantung and feminine colors in shades of poppy pink, grass green, and lemon yellow captivated American women. Although she had an elitist vibe, Jackie’s clothing was actually quite simple and easy to imitate. Like Mrs. Obama, she wore simple sleeveless dresses and coats or boxy suits. She also wrote her own rules, wearing bare arms and bare legs.

Nancy Reagan, on the other hand, arrived at the White House fully intending to socialize. She used her Hollywood style to light up Washington, hosting 55 state dinners, wearing couture gowns by Galanos, and famously ordering up expensive new “Nancy Red” china. As a former actress, she knew about the value of appearances. She was always camera-ready, matching her clothing to the color scheme of sites where she would be photographed.

But by the time Michelle Obama got to the White House, first lady fashion had been on hiatus for quite some time. With her glamorous Peter Soronen evening gowns and her floral print dresses, Michelle has brought a more feminine and fashionable look to the position. Her latest fashion statement, the much-discussed crimson Alexander McQueen dress she wore to the state dinner for Chinese President Hu Jintao, even had a turn on Hollywood’s red carpet—albeit in another form.

Kate Betts is a contributing editor at Time magazine and until this year was also the editor of Time Style & Design. Previously, Betts was the editor in chief of Harper's Bazaar and the fashion news director of Vogue. She is the author of the book Everyday Icon: Michelle Obama and the Power of Style .