Boston: Wellesley, Massachusetts
Exciting and pompous fact: It has America's highest percentage of adults who hold at least one college degree.
As someone who actually grew up in this town, I can tell you I didn't really want to choose Wellesley. I wanted to choose Manchester-by-the-Sea because, I mean, who really does that to the name of their town? Or Dover because of horse stables and surgeons. Or Weston because of mansions that you can't even see from the street. But this is about obnoxious suburbs rather than the wealthiest, and man, current Wellesley really came to play in that category.
The newly revitalized Downtown now has some very solid restaurant choices and even places to drink non-Polar sodas, and that has made it a suburban hotspot of sorts, and driven home prices dramatically higher. And with this influx of wealth has come a new, curiously over-the-top Wellesley attitude, along with houses now built almost to their lot limits, and Range Rovers and those expensive fur vests popular in ski towns. "It's a scene now," one of my friends who still lives there says. "Like a legitimate snobby scene."
Sigh. If you need me, I'll be in the Linden Store, eating two BBQ roast beef subs to mask my emotions. -- K.A.
Charlotte: Ballantyne, North Carolina
Exciting and pompous fact: It has its own damn magazine.
Though it technically remains under the Charlotte city flag, Ballantyne discussed leaving to form its own city in 2012, possibly because Ballantyne's gentry were embarrassed showing up to country-club mixers with the Queen City dressed like that. Full of upscale "shopping and dining conveniences" like Ballantyne Village, Ballantyne Commons East, Ballantyne Quad, and Ballantyne Corners, what really put things over the top was the media kit for the magazine, which touts the "thriving affluent community" filled with "well-educated, sophisticated professionals." I just subscribed. -- K.A.
Chicago: Kenilworth, Illinois
Exciting and pompous fact: The public building in the middle of town is known as the Kenilworth Club. So basically, even its public buildings sound private.
Have you ever walked around Winnetka and thought, "Ugh, these houses are tiny and I feel like not a lot of them have helipads?" Well then, Kenilworth is for you! Basically a wealthy enclave tucked inside a wealthy enclave wrapped up in Chicago's premier North Shore enclave, it was originally purchased by Joseph Sears in the late 19th century to be built as a planned community for white people. And well, not a ton has changed.
The big decision for every Kenilworth family is basically whether to send Chad Jr. and Trip either to Loyola or North Shore Country Day, or roll the dice on their futures and stick them in New Trier with kids from Wilmette, Winnetka, Glencoe, Northfield, and, oh dear God -- even parts of Glenview? Loyola it is. -- K.A.
Cincinnati: Indian Hill, Ohio
Exciting and pompous fact: Legally, it's named "The City of the Village of Indian Hill," because when the population crept north of 5,000 -- requiring a designation of "city" under Ohio law -- residents changed the name to "Village of Indian Hill," just for that extra dash of pretension.
When you're touted as America's best place to raise a family by luxury-humping coffee table occupier The Robb Report, you know you're really nailing the whole elitism thing. (Robb Report has also named best places for yachting and equestrian activities, because let's be real, the nannies are raising the kids anyway.) Where were we? Oh, right, Indian Hill! Ahem, the Village of Indian Hill.
This is the kind of place where combatants in million-dollar real estate disputes hire airplanes to shame their opponents at prominent tennis tournaments. Where the high school lacrosse team is packed with enough Braxtons and Xanders to make you say, "Wait, are you SURE this isn't a Connecticut prep school?" Where they're welcoming to people from all backgrounds, as long as people from certain backgrounds are, like, coaching the Bengals or something. -- Matt Lynch, Thrillist executive editor