Putting the Chic Back in Dressing

If you ask citizens of other countries to paint a portrait of the average American tourist, it would look something like this: a loud, chubby sight-seer wearing a fanny pack, baseball cap, printed T shirt, jean shorts and sneakers. It may seem like a funny, if harmless, image, but combined with the imprint of the outgoing president, the fashion-challenged cowboy in chief, the stereotype of the ugly American has become intractable. The United States has a serious public-relations problem, but the election of President Obama—with his youthful, clean-cut good looks—offers a valuable opportunity for a national top-to-toe makeover.

Yanks haven't always dressed so badly. Consider as evidence the remarkable cable-TV series "Mad Men," with its coterie of early-'60s-era wasp-waisted women, and Don Draper and his advertising-agency colleagues cutting dashing figures in their sober suits. That kind of formality is dead, of course, and with good reason. "Casual is comfortable," says Nicole Phelps, the executive editor of Style.com. "Those girdles and the [silhouette] they created look incredibly chic, but I don't think most contemporary women would put up with the discomfort of wearing one. Nor are they likely willing to put in the time it took to get dressed like that. People are busy. Dress codes have been relaxed. Hats and gloves look like costumes now. Simplicity rules."

It may come as news to the rest of the world, but simplicity—as opposed to sloppiness—is America's true stylistic heritage. The girdles that defined the sartorial shape of the '50s were holdovers of a European influence, the constraints of which American designers energetically threw off as the decades passed. Claire McCardell, Bonnie Cashin, Anne Klein, Perry Ellis, Calvin Klein, Donna Karan—their generous, democratic sportswear freed men and women to live their lives without worrying inordinately about how they looked. Somewhere along the way, however, Americans lost the chic part of casual chic.

They need to get it back. Not just to restore the country's sartorial reputation in the eyes of the world, but because it represents the values Americans hold most dear. The United States was built on the efforts of plain-spoken people who took pride in an honest day's work and who would give their neighbors the plaid shirts off their backs. Those with the means made a virtue of exuding relaxed elegance; they didn't try to overdo anything, but they saw no shame in appearing put together. It was an extension of what they believed in, a polished pragmatism that, today, has given way to self-indulgence.

Comfort has its place, of course, but if that becomes the guiding value in getting dressed—or anything else—then we've got a problem. This misplaced priority has arguably contributed to our current troubles with credit, education and productivity. Compared with our parents and grandparents, we've had it relatively easy. We've got cable TV, microwave popcorn and GPS. The world is at our command and we are at ease, but this kind of comfort breeds complacency—not to mention Velcro straps and elasticized waistbands. We'd be better off showcasing some of the original values that brought us so far.

Contemporary retail offerings don't make it easy. The mass market is defined by a Juicy Couture, pajamas-as-daywear mentality, while the next generation of American design talent is largely caught up in approximating European fashionability, or harking back to "Mad Men"-like looks.