The Bourgeois Bohemian is often what the Hipster or Granola Girl turns into when he/she hits middle age, or what the New Age Retro Hippie might have become had he not dropped out.
The defining trait of the Bourgeois Bohemian (Bobo for short) is that while he belongs to the upper or upper-middle class in economic terms, his values are inherited from the countercultural movements of the 1960s. Expect very open attitudes towards issues such as sexuality and recreational drugs as well as support for liberal/progressive political causes. Fondness for for NPR and PBS is also common. Unsympathetic examples of the trope will often be portrayed as hypocritical about their wealth, criticizing other wealthy elites while sharing much of their lifestyle. "Limousine liberal" (US term), "Champagne Socialist" (UK term), "Chardonnay socialist" (Australian term) or "Caviar leftist" (French term) are some pejorative terms you'll sometimes find applied to this type. Sympathetic portrayals will usually not suggest that anything is wrong or contradictory about liberal values coupled with financial success.
When they show up in fiction, it is often as a main character's Hippie Parents, and they are very likely to live in San Francisco, since that city is known both for being very liberal and for having a very high cost of living.
See also: The Man Is Sticking It To The Man, Rule Abiding Rebel, and Upper Class Twit. If the aging character loses the values themselves as well as the trappings thereof, they become a Former Teen Rebel, which can intersect with Nouveau Riche if they also become wealthy.
The protagonist's parents in The Elegance of the Hedgehog.
The protagonists of Freedom by Jonathan Franzen.
Discussed and critiqued in the non-fiction book The Rebel Sell as part of the shifting values of the political left from old-school socialism to counterculture hipsterism, and how these values have fed the consumer culture they claim to resent.
Similarly discussed in Thomas Frank's 2004 book What's the Matter with Kansas: How Conservatives Won the Heart of America. He charges that many of the U.S. political class's wealthy leftists are not really leftists at all; they are "libertarian" (which in American political parlance roughly equals "moderate conservative") opportunists who feign politically correct attitudes in order to appeal to more upscale (and ostensibly more sophisticated) urban and suburban voters in the "blue states". Conversely, those elites who live in the "red states" generally prefer to act like right-wing culture warriors in order to court the more downscale (and generally more traditionalist) constituents of America's conservative coalition.
1632: Thomas "Stoner" Stone is a last-wave hippie, whose knowledge of chemistry (he made LSD in the sixties) has made him one of the richest men in Europe, with a personal fortune that rivals that of many nations. He is completely devoted to the ideals of peace, love and understanding, in word and deed. For example, he refuses payment for all medicines he makes, only making money from dyes and cosmetics. Profiting from people's vanity is OK, profiting from their pain is not.
Portlandia makes fun of the counter-culture scene of Portland, Oregon. Many characters are middle-aged professionals with bohemian values.
You could also definitely include Warren and Lois Whelan—Debra's wealthy (or at least upper middle-class) parents—from Everybody Loves Raymond. When they first appear, Ray, Frank, and Marie are not looking forward to it, groaning about how much Warren and Lois basically embody this trope to a tee, and how different their own blue-collar family is from the Whelans. When they arrive later in the episode, Hilarity Ensues obviously. Over the course of the series, Warren and Lois continue to embody this trope, leading to more awkwardness (and hilarity) when they and the Barones interact.
George in Bored To Death, played by Ted Danson, is a pot-smoking hippy who runs a magazine similar to The New Yorker. He's quite wealthy, but still has his left-wing lifestyle and opinions. In the second season, he suffers a serious clash of cultures when his magazine is bought out by a right-wing organization.
French Canadian sketch comedy Les Bobos is Exactly What It Says on the Tin: a satirical depiction of a couple of Bourgeois Bohemians living in Montreal's hippest neighborhood.
In Saxondale Tommy Saxondale and Mags are a New Age Retro Hippie and Granola Girl respectively but live in a fairly middle-class suburban neighborhood, and own their own businesses. Of course, being a Brit Com, this contradiction is the whole point of the show.
This sort of character is referenced in Don Henley's haunting hit song "The Boys of Summer", which is about aging and looking back at the past. The particularly poignant line "saw a Deadhead sticker on a Cadillac" paints a harsh image of contrast: The Grateful Dead represented a freewheeling lifestyle (they openly encouraged bootlegging and it is a large part of Deadhead culture), while Cadillacs are expensive symbols of luxury and social status. (The Ataris' cover version changes the sticker to Black Flag, which is ironic conisdering that Black Flag singer Henry Rollins now pitches for Infiniti.)
Henry Rollins is a punk rock icon who now regularly gives spoken-word performances from his liberal point of view. He's obviously made quite a lot of money over the years from his music, acting roles and voice-over gigs. He's now the voice of Infiniti luxury automobiles. He provides a defense of old punk rockers 'Selling out' and allowing their music to appear in advertisements.
"Les Bobos", a song by French singer Renaud, is Exactly What It Says on the Tin: a satirical portrayal of Bourgeois Bohemians. At the end of the song, the singer acknowledges that he may be one of them.
Keating! The Musical has the title character assure the audience that "there's nothing wrong with being inner-city elite" in his first song. Paul Keating, the former Australian Prime Minister on whose career the musical is based, is probably the highest ranking Bobo in Australian history.
Stuff White People Like is generally written from an American, metropolitan, bicoastal, college-educated, liberal point of view, which would include a lot of Bourgeois Bohemian tastes. The initialism "SWPL" is sometimes used by conservative critics as a pejorative term for the type of people described here.
Munchie and Seth in The Simpsons episode "D'oh-in in the Wind."
In the South Park episode "Smug Alert", the adult residents of San Francisco are portrayed as bourgeois bohemians who are so smug and self-satisfied that they enjoy the smell of their own farts.
Though usually simply an Upper Class Twit, Bruce Wayne's (platonic) friend Veronica Vreeland on Batman The Animated Series also donated much of her family's fortunes to conservationist causes, sometimes at fancy public events held to promote those causes. Selina Kyle, who considers herself a true animal-rights activist, once observed that Veronica could possibly be getting involved in those causes because she feels tremendous guilt about all the endangered species her ancestors shot when they were big-game hunters.
New York Times columnist and PBS/NPR correspondent David Brooks coined the term "Bourgeois Bohemian" in his 2000 book Bobos in Paradise... and admits in the book's introduction that he himself probably counts as one.
Celebrities in the entertainment industry are often Bourgeois Bohemians, probably due to their combination of wealth (though many grew up amidst modest settings or even in poverty) and liberal arts backgrounds.
Critics of Michael Moore point out that while he makes documentaries that criticize big business and support working class families, he is himself wealthy and sent his kids to private school.
Examples in the music industry include Barbra Streisand and Neil Portnow, head of NARAS (which gives the Grammy Awards), who once used his annual address at the Grammys to editorialize on the Iraq War.
Hipsters, especially younger and more suburban ones, are generally seen as a junior version of the trope. Teens and especially college kids who espouse strongly liberal, counterculture and anti-establishment views are often criticized for doing so from a position of material comfort, being supported by their parents and lacking experience in the "real world."
In addition to San Francisco, places in the U.S. likely to be considered havens for these types of people include Berkeley and the Westside of Los Angeles in California; Boston, Massachusetts (and the nearby suburbs of Cambridge and Brookline); Seattle, Washington; Portland and Eugene in Oregon; Austin, Texas; Boulder, Colorado; the Twin Cities area in Minnesota; the North Side of Chicago; Madison, Bay View, or Milwaukee's east side in Wisconsin; Ann Arbor, Michigan; Park City, Utah; Hoboken and downtown Jersey City in New Jersey; New York City, especially the gentrified parts of Manhattan and Brooklyn; Washington, D.C; and northern Virginia.
In Britain, there are certain things that are associated with this trope. For instance, people who live in Islington are generally seen as an example, to the point where the word "Islington" itself has become synonymous with this sort of stereotype. Also, people who read the upmarket left-wing paper The Guardian are also seen being this - the paper's editorial slant is towards socialistic, anti-capitalist, anti-consumerist opinions but being a national daily newspaper it still carries the usual magazine features on high-end holidays, fashion, food, restaurants, house-buying etc. There's even an often unintentionally amusing 'Ethical Living' page. The term "Guardianista" has become the rightpondian equivalent of "latte-liberal".
British Labour prime minister Tony Blair came in for heavy criticism when it emerged one of his children had been sent to a private school instead of a state school.