In October 1987, Newsweek ran a cover story on would-be presidential candidate George H. W. Bush with the blaring headline “Fighting the Wimp Factor.”

That Bush was a World War II combat pilot, well over six feet, athletic, and a genuinely nice guy mattered little. Apparently, the fact that he had been Reagan’s subordinate for eight years, sounded nasal at times, and lapsed into occasional stuffy metaphors created an impression — fueled by everyone from the Newsweek editors to Jimmy Carter — that Bush was a wimp. He dispelled that for a time in 1988 (opponent Michael Dukakis, awkwardly perched in an Abrams tank, helped), but down-home good ol’ boy Bill Clinton exploited the preppy charge again in 1992, to some effect. Stereotypes, in other words, die hard.

Yuppism, remember, is not definable entirely by income or class. Rather, it is a late-twentieth-century cultural phenomenon of self-absorbed young professionals, earning good pay, enjoying the cultural attractions of sophisticated urban life and thought, and generally out of touch with, indeed antithetical to, most of the challenges and concerns of a far less well-off and more parochial Middle America.

For the yuppie male, a well-paying job in law, finance, academia, or consulting in a cultural hub, hip fashion, cool appearance, studied poise, elite education, proper recreation and fitness, and general proximity to liberal-thinking elites, especially of the more rarefied sort in the arts, are the mark of a real man.

For Obama, all the self-referencing about his black heritage and his tough community organizing, the publicly shared confessions about his absent father, the Chicago “bring a gun to a knife fight” tough talk, and the “cool” manner of shooting hoops cannot quite erase the image of an aloof, whiny urban professional of the sort who likes having nice things and kicking back, has not a clue about the lives of the middle and working classes, and heretofore has worried mostly about his own upward mobility.

In that context, for the Obamas, if there were not a Martha’s Vineyard or Costa del Sol, such places would probably have to be invented. Barack Obama — the son of a Ph.D. and a Harvard-educated economist, graduate of a Hawaii prep school, replete with Ivy League education, stylish digs in a good Chicago neighborhood, properly tamed and presentable radical social circles, and the requisite power-couple marriage — appreciates the ambience of a vacation spot: Who goes there and why, and what others will say and think, alone matter. Otherwise, the sun and surf at Pismo Beach would do just as well.

During the campaign, numerous critics highlighted what we can legitimately call Obama’s yuppie problem — especially after the good times ended with the September 2008 meltdown, and a frazzled public wanted a president who would symbolically appreciate their ordeal. Instead, Obama wondered out loud about the price of arugula. He could not bowl a lick (but foolishly tried), and he scoffed at the gun-owning, white churchgoers of rural Pennsylvania as hopeless clingers, just the sort you would not want to meet at a Bill Ayers book-signing party in Hyde Park.