The lighter side of real estate

The 10 Preppiest Cities in America

Think you know which cities have the most popped collars and country clubs? You’ll be surprised by what the data says.

Randy Nelson

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119 articles, 53 comments

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Ah, the preppy life. You wake up in the morning, slip into your khakis and polo shirt, pop, the collar, and meet up with your college friends for brunch at the country club (you cover the bill). In the afternoon, you pick up your youngest from private school and check the mail to find a letter from Billy in boarding school, telling you that college prep is going just swell. Then it’s time for some tennis… or was it polo, or golf? There are just so many choices here in Preppy Land. Whatever you choose, you can always do something different tomorrow, since you’re a member—and membership has its privileges.



Here at the Movoto Real Estate blog, we realize that America is made up of countless subcultures, and we’ve made it a sort of mission to find out which cities they actually call home (well, except for hipsters, that is). For our latest bit of Saturday Night Science, we decided to turn our lens on the preppy, that ever-smiling, perpetually well-off subset of society that gravitates toward quality, classic clothing, equestrian sports, and country club living. Oh, and preparatory schools. Gotta have those.

Now, you probably think you know where the preppiest cities in America are already. They’re all in the Northeast, right? New England, or if they could possibly be somewhere else, it’s probably coastal. Well, we thought so, too. Until we ran the data, that is.

After sipping a mimosa and browsing the L.L.Bean catalog for a bit, we pored over our criteria and determined that, based on it, the preppiest big city in the nation is on the West Coast, and it’s San Francisco, CA. Anyone who’s ever taken a stroll through the Marina, driven around Nob Hill, or just gone shopping in the city can attest.

San Fran is joined in its preppiness by a top 10 list that certainly holds some surprises:

1. San Francisco, CA
2. Scottsdale, AZ
3. Honolulu, HI
4. Raleigh, NC
5. Seattle, WA
6. Boston, MA
7. Charlotte, NC
8. Plano, TX
9. Portland, OR
10. Washington, D.C.

They’re only surprises, though, until you consider what really makes a city preppy. That’s exactly what we did, and it resulted in a set of criteria against which we ranked the country’s most populous cities in terms of preppiness. We’ll explain all that—and divulge the full top 50 ranking—below.

How We Did It

Regular readers of the blog will know our process by now, but for those who’re newcomers—new members of our very own city ranking country club, if you will—here’s how it works. In order to rank cities by fun stuff like their nerdiness or, in this case, preppiness, we come up with a set of criteria that we feel can be used to measure such things. This time, we used:

  • Number of preppy clothing retailers per capita
  • Country clubs per capita
  • Equestrian centers per capita
  • Private schools per capita
  • Presence of boarding/preparatory schools
  • Percentage of college graduates with a bachelor’s degree or higher
  • Median household income

We then looked up data for these criteria using resources including, Yelp, retailer websites,,, and the U.S. Census for the top 100 most populous cities in America. Once the data was acquired, we ranked each city from one to 100 across all the criteria, with one being the best. We used the average of these scores to determine each city’s final Big Deal Score, the number we used to determine their overall preppiness. The lower this number, the better—and the more preppy.

Some things of note: We only considered retailers, schools, country clubs, etc. that are actually located within the cities proper, not the metropolitan areas. Also, since preppiness is largely about a particular look and lifestyle, we weighted the ranking towards preppy retailers, high incomes, and prep schools.

In the following section, we’ll go over why we picked each criterion and how specific cities stacked up when measured against them, so cinch up that ascot and come along.

Prep Schools: They’re Not Just in the Northeast

Let’s start with the origin of the term “preppy” itself: college preparatory schools. From a list of all prep schools in the U.S., we gave points to cities on our overall list of 100 for having one within their city limits. As it turns out, only 17 of the 100 most populous cities in the country have at least one:

Preppy Stores: Popped Collars and Socks-less Shoes

Source: Flickr user Magda Wojtyra

Source: Flickr user Magda Wojtyra

We’re not going to deny it: A huge factor in overall preppiness is simply looking the part. While you can find clothing from classically preppy brands such as J.Crew, Ralph Lauren, and Tommy Hilfiger at your local Macy’s, we figured that truly preppy locales are going to be important enough to these brands that they’ll have stand-alone stores there. So, we tracked down how many of those there are per capita in each city.

Orlando, FL strolled out with a win wearing deck shoes in this category, with one preppy retailer for every 40,533 residents. Las Vegas, NV came in a distant second with one for every 84,188, while Greensboro, NC has one for every 91,142.

Country Clubs: The Preppy’s Home Away From Home

Being accepted into a private country club is kind of like a preppy badge of honor, and we figured that any city with a high degree of preppiness is going to need more of these institutions per capita to keep up with demand. Also, they’re typically where those of the preppy persuasion will partake in a game of tennis or round of golf, two of the most popular preppy sports (polo, bocce ball, and croquet being some others).

Newark, NJ has a lot of country clubs. In fact, it has one for every 4,704 residents. Not too far behind is Chandler, AZ, which has one for every 7,745 folks who live there. Orlando, FL makes the individual ranking once again with one country club for every 9,354 people in its part of the Sunshine State.

Private Schools: Where It All Begins

Before prep school and college, the educational career of the preppy begins in private elementary, middle, and high schools. It’s also common for preppies to place their kids into private school when it’s time for the young ones to begin their schooling. For this reason, we factored in how many of these institutions there are per capita in each city on our list of 100.

San Francisco, CA is a private school paradise, with one for every 6,451 residents. Not too far behind it, with one for every 7,929 people, is Honolulu, HI. In third place with one for every 9,431 residents is Fremont, CA.

Equestrian Centers: Hold Your Horses

Some preppy sporting activities involve horses, and they also need venues to house and perform on these regal animals. That’s why we picked equestrian centers and stables for our ranking. Preppies put their equine friends up, participate in dressage competitions, and travel to and from the polo fields from these horsie hotels.

Scottsdale, AZ trotted to a victory in this category, with one equestrian center for every 22,102 residents. Anaheim, CA has one for every 42,670 residents and Oakland, CA placed a close third with one per every 43,980 people.

Yacht Clubs: Prepare the the Sails

Source: Flickr user Donan Raven

Source: Flickr user Donan Raven

When they’re not getting their fill of fancier sports from riding on horseback, you’ll often find preppies sailing. Sorry, we mean yachting. They’re not alone, either. There are yacht clubs all across the U.S.—anywhere there’s enough water, really—where preppies gather to discuss and promote their aquatic sport of choice. That, and generally be preppy.

You’ll find the most yacht clubs per capita in Toledo, OH, of all places, which has one for every 28,604 residents. Another Ohio city, Cleveland, placed second with one for every 39,381 people. The only coastal city to place in the top three, Long Beach, CA, was third with one for every 42,325 residents.

College Graduates: What All That Prep Work Was For

All that time in prep school has a purpose: to get into college. Not just any college, but a good one—and do really well once you get there. Well enough, we figured, that you’d leave with at least a bachelor’s degree. So, we linked the percentage of people in each city who achieve just that to the place’s overall preppiness.

It turns out that a full 65 percent of the residents in Irvine, CA have at least a bachelor’s degree from college. Seattle, WA residents rank second at 55.8 percent, while the folks in San Francisco, CA are at 54.1 percent.

Median Household Income: This Lifestyle Isn’t Cheap

For our final criterion, we factored in the almighty dollar. It’s an unavoidable fact that living the preppy lifestyle is expensive, what with all those country club and yacht club memberships. Thankfully, with all that college learning comes higher-paying jobs, which at least partially contribute to a higher median household income. We looked at how much households make across our 100 city lineup and ranked them accordingly.

At number one is Fremont, CA, whose households earn an average of $98,513 per year. This Bay Area city is followed by Honolulu, HI, where households bring in $93,439 yearly on average. In third place, Irvine, CA households make $92,599 annually.

Welcome to Preppyville, USA

When everything we found was averaged out, San Francisco, CA shot to the head of the class as America’s Most Preppy City. So, if you’re looking to adopt this luxurious lifestyle—or at least pretend that you have—we suggest that you put down the roof on the Benz convertible, put on your most expensive pair of Wayfarer sunglasses, and get yourself to the City by the Bay. We’ll be waiting for you at the polo field with a picnic packed in our new L.L.Bean basket.

(click to enlarge)

Most Preppy Cities Table

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posted on: September 10, 2013
52,251 views, 11 comments


  1. Tim

    Randy: Not sure how your list defined “prep school”, but you clearly missed lots of cities with prep schools in them. How are you differentiating “private” schools from “prep” schools? A prep school is a private high school, usually non-denominational, whose core mission is to prepare their students for entrance to selective colleges. You can find these types of schools in almost every major city, especially in the east.

    • Randy Nelson in response to Tim

      Hey, Tim. We turned to a directory of the private prep schools across the country and found that most of the major cities were in proximity to one, but the cities I listed actually had at least one actually located within their city limits. Most are in smaller communities that don’t rank among the top 100 most populated cities.

      • Tim in response to Randy Nelson

        Something is still amiss with your “prep school” ranking column. You indicate that there are no “prep” schools in cities like Seattle, Portland, Denver, Minneapolis, St. Paul, etc (any city with a 150 score), but in fact there are several private “prep” high schools in those cities. Are you perhaps only counting boarding schools in your prep school count? That would be a mistake. Most prep school are non-boarding…

      • CTCladdagh in response to Randy Nelson

        DC has the National Cathedral School, St. Albans, Georgetown Day, Washington International School … the list goes on.

        I don’t know what list you were using, but you missed many.

  2. BTinSF

    Sorry but those retailers you called prep are strictly faux prep. The preppiest brand in America may be J. Press, not J.Crew. They only have stores in New York, New Haven, Cambridge MA and Washington DC (Georgetown). Brooks Brothers and Paul Stuart get points and there are a few others including small places like Vinyard Vines for the older once-prep crowd. Another once-prep brand, Orvis, recently folded its tent in San Francisco sadly which means San Franciscans have to buy online the outerwear brand preps share with the British royals: Barbour.

  3. sara

    please don’t say San Fran.

  4. Hcat

    Is Newport Beach, California, too small to make your list at 80,000? Since the 1970s it has arguably been America’s preppiest city.

  5. KA

    I am from Portland Oregon and I can say without a doubt…it is a hipster/hippy city. Not preppy at all. Glendale, Ca was #18 on the list and it’s not preppy either. Newport Beach is preppy. I don’t mean to sound like a Debbie Downer, but I don’t think your information is accurate.

  6. Sean

    As a native Bostonian, I find this truly laughable. Seriously. Especially since I’ve also lived the last 13+ years in San Francisco. And never since Day One would the “P” word ever rush to my lips to describe SF. Boston = DUH. A completely different cultural mindset. Not a whiff of that truly Ivy League vibe to be found on the west coast. (Point to an approximate Nantucket or Harvard Yard. And please don’t retort: Stanford Main Quad. Beautiful yes. But uhm… Spanish roof tiles, palm trees…?) West coast blank stares often accompany the mention of ‘old money’. In SF, most folks would think: “Oh. You mean the first dotbubble back in 2000, right?”

    Another one of those computer generated ‘studies’ based purely on armchair aggregate data. Cynically cranked out to push eyes to a real estate site. Goes without saying the authors of this ‘study’ never actually set foot on the streets of SF and walked around to soak in the culture? Likewise Boston and other cities. SF = tattoos, piercings, hipsters; Boston = plaid, docksiders, grad students.

    Also probably skewing this data is SF often translates into “Bay Area” – which can be quite large depending on your definition. While Boston/Cambridge much less so. (Or does all the data considered within say 25 miles of each city’s downtown?) Again, as most have already mentioned: this ‘study’ is woefully without context.

  7. justin

    Obviously you have never been to Fairfield County CT!!! A 100k salary is a joke and prepped DONT wear J Crew!!

  8. brendan

    Jersey city… not preppy. visit there sometime.


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