When Laura Bush and Hillary Clinton arrived at the White House, they brought with them styles that suited their hometowns in Texas and Arkansas, but that wouldn't have held up in any fashion capital.
Tastemakers have higher hopes for Michelle Obama, who is expected to fill her closet at 1600 Pennsylvania Avenue with sophisticated styles that match her modern image but maintain the sensibility inherent to Chicago.
The image of Obama walking the inaugural parade route in something like the domed, wide-brimmed hat that has haunted Clinton since 1993 seems unlikely. And she probably won't show up to the inaugural ball in mother-of-the-bride-style gowns with dyed-to-match pumps like Bush has worn — twice.
Over time, both Clinton and Bush did grow more accustomed to their new surroundings, and their wardrobe reflected that.
For example, Bush wore a Sunday-best peacock blue coat with sensible shoes to the chilly inaugural ceremony in 2001, but chose a chic winter-white coat ensemble with camel-colored high heels — a top pick of fashion insiders — in 2005.
Clinton also chose a modern, luxe gold lace gown by Oscar de la Renta for her second tour of inaugural balls unlike the fussy purple princess number the first go-around. (Remember the sparkly belt buckle?)
Still, Bush and Clinton fit into the expectations of what earlier generations thought a president's wife should look like. Obama has the opportunity to break the mold.
"Most previous first ladies have appeared to believe that displaying an interest in fashion and style undermines the importance of their role. They've subscribed to the old-fashioned view that a woman should de-sexualize herself or dress like a man if she wants to be regarded as intelligent and of good conscience," says Mandi Norwood, the former editor in chief of Shop Etc. who is now writing a style guide directed to Obama for publisher Avon A.
"Mrs. Obama, however, has a much more modern view," Norwood says. "She's demonstrated that it's smart to be stylish; that strong and positive statements can be made through the right choice of outfit."
The right outfit can't be too cutting edge, though, says Andrea Reynders, chair of the fashion department at the Art Institute of Chicago. This is where Obama's roots will come in handy.
"Trends seem to happen on both coasts, but in the Midwest we look for the value in clothing. Chicago is a wonderful place where you can find women buying garments with wonderful fabrics, detailing and fit. It lends itself wonderfully to a strong classic fashion with a lot of independence — and not being too trendy will serve Michelle well in Washington," Reynders says.
While Clinton also grew up in the Chicago suburbs, her pre-White House adult life was largely spent in Little Rock and her eye adjusted to the local look, says communications consultant Ruth Sherman, who advises business leaders, celebrities and politicians.
So far, Obama has chosen designers that alternately appeal to style insiders and everywomen. They range from retail giant J. Crew to fashion favorite Narciso Rodriguez to Chicago's own Maria Pinto.
Pinto, who was a student of Reynders, epitomizes what Chicago style is — and what Obama needs to do, the professor says: Take a good silhouette, embellish it enough to get noticed, but don't go over the top.
By making some off-the-radar choices, Obama already greatly reduces her risk of making the same faux pas as Bush did at a 2006 Kennedy Center Honors event when she wore the same red de la Renta gown as three other women.
There is so much to consider when developing a first lady's wardrobe — and the rush to do it in a few short weeks between Election Night and moving day further complicates things, says Michael Faircloth, the Dallas-based designer who outfitted Bush.
He says he tried to add touches of Texas by using bright colors and native fabrics such as cotton and mohair.
"In creating Mrs. Bush's inaugural wardrobe, I wanted to convey confidence and graciousness, but there's a certain level of femininity and appropriateness that needs to be there too, and you need to strike a celebratory tone," he says.
A first lady should simultaneously appear graceful and formal, Faircloth adds, and the garments themselves must photograph well.
(Obama may have learned that lesson firsthand when the black sides of her red Rodriguez dress seemed to disappear into the backdrop in Election Night pictures.)
Once she arrives in Washington, Obama should stay true to herself, says Sherman, author of "Get Them To See It Your Way, Right Away."
But Sherman also wonders what will happen to Obama's sometimes-sportier look, one that likely resonates with the younger people who so strongly support her and her husband.
"If the Obamas are being considered the next generations of leaders, will the Obamas reflect that this generation is so much more casual? What does it mean when you see Michelle Obama in jeans? ... Are people's tongues going to be wagging or is it part of her job to appeal to that generation?"
Reynders hopes Obama will look further back in first-lady history and follow the model of Jackie Kennedy — whom Obama has already been compared to many times.
"There was not a `don't' in the lot of Jackie's wardrobe. She matched the figure and fashion of the time," she says.