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44 First Lady Fashion Looks from Eleanor Roosevelt to Michelle Obama

3 minute read

Michelle Obama probably has a long list of things she’d like to be remembered forlike her initiatives to combat childhood obesity and promote higher educationbefore she’s remembered for her sense of style. But with great responsibility comes great clothing, and the First Lady will certainly go down as the most fashionable woman in the White House since Jacqueline Kennedy.

Obama is known for choosing the patterned dress over the more subdued pantsuit, for baring her toned arms and—perish the thought—even wearing shorts. And there are some who argue that the choices she makes transcend personal expression and petty analysis and carry a certain amount of cultural significance.

“For some reason in this country there’s this false notion that style and substance have to occupy two separate worlds,” said fashion journalist Kate Betts in an interview with CNN, “and I think she’s proving that that’s wrong.”

See Michelle Obama's Best Outfits of 2014

Michelle Obama Best Dresses Outfits 2014
After being criticized for wearing a sparkly sleeveless dress to the 2013 State of the Union, Obama went with a more conservative ensemble by Azzedine Alaia for the 2014 State of the Union Address. Drew Angerer—EPA
Michelle Obama Best Dresses Outfits 2014
Never one to shy away from color, Obama donned a bold red coat for a visit from French President Francois Hollande in February.Pete Marovich—Bloomberg/Getty Images
Michelle Obama Best Dresses Outfits 2014
Obama won plaudits for this powder blue and black lace gown by Carolina Herrera, which she wore to a state dinner with Hollande in February.Evan Vucci—AP
Michelle Obama Best Dresses Outfits 2014
During a visit to Beijing in March to meet with Chinese President Xi Jinping, Obama wore a custom dress by Naeem Khan which updated the traditional Chinese red dress — and her daughters didn't look too bad either. Andy Wong—Pool/AFP/Getty Images
Michelle Obama Best Dresses Outfits 2014
The first lady doesn't just own formal wear. For this visit to a Beijing school that prepares children to study abroad, she dressed casually, but with flair.Andy Wong—Pool/Getty Images
Michelle Obama Best Dresses Outfits 2014
For this February appearance on "The Tonight Show" with Jimmy Fallon, Obama went with a sleeveless jumpsuit, showing off her toned arms.NBC/Getty Images
Michelle Obama Best Dresses Outfits 2014
The White House Correspondents' Dinner is often jokingly called Nerd Prom, but Obama's choice of a grey tulle embroidered dress from Marchesa was neither nerdy nor prom-like.Olivier Douliery—Pool/Getty Images
Michelle Obama Best Dresses Outfits 2014
The devil may wear Prada, but Obama went for another Naeem Khan when she met fashionista Anna Wintour at a ribbon-cutting in May.Paul Zimmerman—WireImage/Getty Images
Michelle Obama Best Dresses Outfits 2014
Returning from the dedication of the National September 11 Memorial and Museum, Obama aimed for a subdued but still classy look.Saul Loeb—AFP/Getty Images
Michelle Obama Best Dresses Outfits 2014
The president may have gone for jeans, but Michelle Obama was ready for summer, wearing a crisp white summer dress to the White House Fourth of July celebration.Brendan Smialowski—AFP/Getty Images
Michelle Obama Best Dresses Outfits 2014
For a luncheon at The Grammy Museum in July, Obama once again went sleeveless in a white dress from Phillip Lim. Jason LaVeris—FilmMagic/Getty Images
Michelle Obama Best Dresses Outfits 2014
During a visit to New York for the United Nations General Assembly, Obama wore a colorful wrap from Diane von Furstenberg.Saul Loeb—AFP/Getty Images
Michelle Obama Best Dresses Outfits 2014
At an awards dinner held by the Congressional Black Caucus Foundation, Obama chose a dress from Bibhu Mohapatra's fall collection.Nicholas Kamm—AFP/Getty Images
Michelle Obama Best Dresses Outfits 2014
No ugly Christmas sweaters in sight as Obama, daughters Malia and Sasha and the family dogs greet the White House Christmas tree. Joshua Roberts—Bloomberg/Getty Images
Michelle Obama Best Dresses Outfits 2014
Ending the year in style, and mirroring the White House Christmas decorations, Obama wore this dress by Monique Lhuiller to the Kennedy Center honors in December. Brendan Smialowski—AFP/Getty Images

According to Betts, author of Everyday Icon: Michelle Obama and the Power of Style, Obama’s style choices convey comfort (the occasional flats), confidence (feminine florals) and relatability (she shops at J. Crew). Her effortless looks, Betts wrote in the New York Times, make it “hard to imagine that there had ever been any dress code for her position.”

As these photos by LIFE photographers show, there hasn’t exactly been a dress code, though styles have historically erred on the conservative side (in terms of hem lines, not party lines). The first ladies’ fashions have both evolved with popular trends and helped to inspire them. Furs, seen on Eleanor Roosevelt, Bess Truman, Mamie Eisenhower and Lady Bird Johnson, have fallen out of favor in recent decades. Hats, from Truman’s rather vertical design to Kennedy’s pillbox style, are infrequently sported by recent first ladies. Leather, with the exception of Nancy Reagan, shown in 1968 before her First Lady days, has been far from a staple, whereas the simple pearl necklace continues to be a timeless, nonpartisan classic.

While Kennedy’s style was described by LIFE in 1961 as having “an almost deliberate plainness,” Obama does not shy away from a hint of flourish here and there. But she’s certainly not the first to indulge in a bit of flair. When working with a designer on her dress for the inauguration in 1953, Mamie Eisenhower had a few extra requests. “She specified pink and asked for some additional glitter.” Because even the White Houseno, especially the White Housecan use a little sparkle now and then.

Liz Ronk, who edited this gallery, is the Photo Editor for LIFE.com. Follow her on Twitter at @LizabethRonk.

Eleanor Roosevelt, 1937
President Franklin D. Roosevelt with his wife Eleanor voting in a Hyde Park polling station, 1937. Pictures Inc.—The LIFE Picture Collection/Getty Images
Eleanor Roosevelt, 1937
Eleanor Roosevelt with Doris Fleeson, 1937.Thomas D. McAvoy—The LIFE Picture Collection/Getty Images
Eleanor Roosevelt, 1942
Eleanor Roosevelt walking and talking with the commanding officer of a group of American paratroopers, 1942.David E. Scherman—The LIFE Picture Collection/Getty Images
Bess Truman, 1946
Bess Truman sitting at a desk, 1946.Marie Hansen—The LIFE Picture Collection/Getty Images
Bess Truman, 1946.
Bess Truman waving to crowd as her husband, President Harry S. Truman, and daugther Margaret look on during Army Day, 1946.George Skadding—The LIFE Picture Collection/Getty Images
Bess Truman, 1949
Bess Truman looking over a table full of baked goods, 1949.Francis Miller—The LIFE Picture Collection/Getty Images
Mamie Eisenhower, 1948
General Dwight D. Eisenhower walking with his wife Mamie, 1948.Francis Miller—The LIFE Picture Collection/Getty Images
Mamie Eisenhower, 1953
Mamie Eisenhower posing in her inaugural ball gown with a jeweled purse encrusted with 3,456 pink pearls, 1953.Nina Leen—The LIFE Picture Collection/Getty Images
Mamie Eisenhower, 1958
Mamie Eisenhower at the North Portico, 1958. Featured on the cover of LIFE. Ed Clark—The LIFE Picture Collection/Getty Images
Pat Nixon, Mamie Eisenhower, Lady Bird Johnson, Jackie Kennedy - 1961
Four past, present and future first ladies at President John F. Kennedy's inauguration ceremony, including (L-R) Pat Nixon, Mamie Eisenhower, Lady Bird Johnson and new First Lady Jacqueline Kennedy, 1961.George Silk—The LIFE Picture Collection/Getty Images
Jackie Kennedy, 1960
Presidential candidate John F. Kennedy riding in car with wife Jackie Kennedy upon return home from Democratic National Convention, 1960.Paul Schutzer—The LIFE Picture Collection/Getty Images
Jackie Kennedy, 1962
President John F. Kennedy and his wife Jackie chatting with poet Robert Frost at a party for Nobel Prize winners at the White House, 1962.Art Rickerby—The LIFE Picture Collection/Getty Images
Jackie Kennedy, 1962
First Lady Jackie Kennedy standing on the grounds of the Taj Mahal during visit to India, 1962.Art Rickerby—The LIFE Picture Collection/Getty Images
Jackie Kennedy, 1962
Jackie Kennedy on the first day of a trip to India, 1962.Art Rickerby—The LIFE Picture Collection/Getty Images
Lady Bird Johnson, 1961
President of Senegal Leopold Senghor with Mrs. Lyndon B. Johnson during the first anniversary of independence from France, 1961.Hank Walker—The LIFE Picture Collection/Getty Images
Lady Bird Johnson, 1964
Lady Bird Johnson, 1964.Stan Wayman—The LIFE Picture Collection/Getty Images
Lady Bird Johnson, 1964
President Lyndon Johnson sitting on porch swing with wife Claudia (Lady Bird) on the morning following his landslide election win, 1964.John Dominis—The LIFE Picture Collection/Getty Images
Pat Nixon, 1952
Richard M. Nixon and his wife Pat talking with photographers during the 1952 convention.Ralph Morse—The LIFE Picture Collection/Getty Images
Pat Nixon, 1958
Vice President Richard Nixon and his wife Pat in formal dress reflected in oval mirror, 1958.Hank Walker—The LIFE Picture Collection/Getty Images
Pat Nixon, 1968
Pat Nixon, wife of presidential candidate Richard Nixon, on the campaign trail, 1968.Arthur Schatz—The LIFE Picture Collection/Getty Images
Pat Nixon, 1972
Chinese premier Chou-En-Lai, First Lady Pat Nixon and Secretary of State Henry Kissinger during Nixon's visit to China, 1972.John Dominis—The LIFE Picture Collection/Getty Images
Betty Ford, 1973
Newly appointed Vice President Gerald R. Ford with wife Betty and (clockwise from L) daughter Susan, sons John and Steve at home, 1973.Alfred Eisenstaedt—The LIFE Picture Collection/Getty Images
Rosalynn Carter, 1971
Georgia Governor and future American president Jimmy Carter kissing his wife, Rosalynn, 1971.Stan Wayman—The LIFE Picture Collection/Getty Images
Nancy Reagan, 1966
California gubernatorial candidate Ronald Reagan holding hands with wife Nancy while on the campaign trail, 1966.Bill Ray—The LIFE Picture Collection/Getty Images
Nancy Reagan, 1967
Nancy Reagan, 1967.Fred Lyon—The LIFE Picture Collection/Getty Images
Nancy Reagan, 1968
California Governor Ronald Reagan with wife Nancy, hosting social evening during conference of GOP governors, 1968.Arthur Schatz—The LIFE Picture Collection/Getty Images
Barbara Bush, 1971
Future First Lady Barbara Bush on the golf course, 1971.Leonard McCombe—The LIFE Picture Collection/Getty Images
Barbara Bush, 1971
Ambassador George H.W. Bush and wife Barbara, 1971.Leonard McCombe—The LIFE Picture Collection/Getty Images
Hillary Clinton, 1969
Class leader and future First Lady and Senator Hillary Rodham (later Clinton) of Wellesley College talking about student protests which she supported in her commencement speech, 1969.Lee Balterman—The LIFE Picture Collection/Getty Images

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Write to Eliza Berman at eliza.berman@time.com