Preppy Winter Essentials - What Ever Gentlemen Needs for an East Coast Winter

It's that time of year again! Here on the east coast we had a great summer, but as we draw into November, winter is fast approaching.  This past September, I began my collegiate career at Sarah Lawrence College in beautiful Bronxville, NY.  As a native son of New England, I was well equipped for the colder weather, but many of my new friends from the west coast were not.  I recently went shopping with a friend of mine from Long Beach California who asked me to show him all the winter fashion essentials.  That little shopping trip inspired this post.

LL Bean Bean Boots-

There's no fashion label as iconically New England as LL Bean and the duck boot style Bean Boots were the product that made them a household name. Originally designed for duck hunting in the wilds of Maine, they quickly became a fashion icon for wealthy New Englanders.  Today they remain as popular as ever and not without reason; their great quality and their signature design has never changed.  There have, of course, been several knock offs, but you really can't beat the originals.  We all need good footwear for the upcoming snow storms, and as we've said, you can't go wrong with a classic.  It's worth noting that boots like this can be worn all through the spring and autumn months, but in the winter they are a necessity, particularly if you live in the New England area.

Barbour Beaufort Jacket

Here we have another preppy fashion icon.  It's been stated that everyone who ever attended prep school has owned a Barbour jacket in signature bottle green.  One benefit to these jackets, as every prep school student knows, is that their just long enough to cover a navy blue blazer.  Of course, though, these great jackets do more than just cover up; they also keep you warm and offer excellent protection form the rain, so you can see why they'd be popular among east coast prep school students.  You can also wear one skiing, although if you're going out in a blizzard, you'll likely want something heavier. That said, though, these Barbour jackets are iconic, they look great, and they can easily be slipped on en route to a formal occasion.  Definitely an item that belongs in every preppy wardrobe.

Patagonia Fleece
This is technically more of an autumn item, although they certainly carry into the winter as well.  A company founded in California, Patagonia likely didn't expect to be catering to the wealthy, but their high quality gear has risen to great popularity among the prep school crowd, particularly on the east coast.  It makes sense, though, as the cold and ever-changing weather of New England definitely calls for fleeces.  Their the perfect accessory for fall and in the winter, you can easily slip a ski jacket or parka over it for additional warmth.  The Patagonia logo has become almost as iconic in the preppy community as the Ralph Lauren polo player, the Lacoste alligator, or the Vineyard Vines pink whale.  The North Face is a runner up, but this is a brand you really can't beat for comfort and style.  If you can't get a Patagonia, grab a fleece from The North Face, another quality maker of great winter gear.

LL Bean Norwegian Sweater 
Like Bean Boots, You'll find plenty of knock-offs of this iconic fashion item from unknown brands, but the originals are from LL Bean and their the company that made the Norwegian sweater cool in this country and popular among the preppy crowd.  Very warm and soft, these items first rose to popularity among skiers, as they were ideal for wearing under a parka.  Of course the overwhelming number of preppy kids who ski and snowboard soon caught onto the trend.  The Official Preppy Handbook tells us that every student at St. Lawrence University (one of the preppiest colleges) owns at least one Norwegian sweater, which could make sense, given the incredible skiing in the area of Canton New York which the school is located.  If you're someone who likes to ski or snowboard, or just wants to stay warm this winter and look great while doing it, grab one of these.  Their iconic, they look great, and they really will keep you warm on the slopes.

Beyond Gatsby: The Preppy Reading List

Not too long ago, I passed a Tommy Hilfiger, with one of the best photos ads I had ever seen displayed in the window.  Instead of the typical attractive, young people dressed in very preppy clothes, it featured a large drawing of three leather-bound books on a shelf, one of which was titled "Timeless Tales of Prep."  Although no such book exists, I had to ask myself what the best preppy books were.  We've supplied a list of our prep/boarding school favorites. Read on.

The Catcher in the Rye - J.D. Salinger
Although the prep school plays a small part in it, America's favorite preppy book seems to be J.D. Salinger's timeless classic The Catcher in the Rye.  It's one of my favorite novels and I can't recommend it highly enough.  When we first meet Holden Caulfield, the books' narrator and hero (sometimes referred to as an anti-hero), he is a student at an elite east coast prep school known as Pency Prep.  Holden is the son of a wealthy corporate lawyer, but at the start of the book, he is about to flunk out of school entirely.  After arguments with his roommate and another student who he doesn't get along with, Holden escapes to nearby New York City, where he is from, wanting to avoid breaking the news to his parents for a few days.  That's just where the story starts.  Although it isn't completely about preppy things or people, every preppy bedroom should include a well-loved copy of this book or a brand new one because the one you read at boarding school fell apart.



This Side of Paradise - F. Scott Fitzgerald
We all know the story of the great Jay Gatsby and some of you may have even read Tender is the Night, but so few people seem to be acquainted with Amory Blane, the hero of F. Scott Fitzgerald's most underrated novel.  Amory is the classic son of privilege, born into a prominent mid-west family and sent to an elite Connecticut boarding school and later educated at Princeton University (so prep it hurts).  That's just beginning, though, as Amory takes off on a journey through life and self-discovery, ending with the iconic phrase "I know myself.  But that is all I know"  This Side of Paradise is Fitzerald's memoir of sorts, said to have been inspired by events from his own life.  One of the most iconic figures of prepdom, Fitzgerald was himself educated at an elite boarding school followed by...you guessed it, Princeton.  This is truly the best American novel concerning prepdom.  Though the prep school plays a small part, Amory is unquestionably the preppiest character to ever have been born in American literature.

A Separate Peace - John Knowles
Finally, we come to a novel that takes place entirely at a prep school.  Written by John Knowles, a graduate of Phillips Exeter Academy and Yale University, it tells the story of Gene, the lonely, introverted intellectual new kid at the prestigious Devon School, an elite New England boarding school.  The first in his family to attend prep school, Gene doesn't quite feel like he belongs, particularly when he meets Finny, his wealthy roommate.  Handsome, charming, daring, and athletic, Finny is everything Gene is not, yet he finds him oddly fascinating and as the story unfolds, we learn why, particularly as the boys discover why that they both need each other while Gene harbors a guilty secret.  Meanwhile, as their country hovers on the brink of WWII, the boys of Devon face decisions that will affect them not just at school, but in the world beyond.  It all leads up to an emotional climax that no one could have predicted.



The Rector of Justin - Louis Auchincloss
First published in 1964, this quintessential prep school novel spent over 8 months on the bestseller list.  Contrary to what the book's cover (left) might suggest, it is actually not the story of a scared little boy who enters prep school for the first time.  Moreover, it tells the story of Dr. Francis Prescott, the founder and head of an all boys Episcopal prep school, located in New England.  It is told from the point of view of many people who knew him.  While some loved him, some couldn't stand the man and others feared him.  Told by a group of interesting and varied voices, it covers the extraordinary man's journey over the course of his whole life, from his boyhood to beyond his death.  The author, the renowned Louis Auchincloss was an alum of the prestigious Groton School in Groton Massachusetts and Yale University as well as the University of Virginia Law School.  His prep school background is certainly reflected in his writing.

New Boy - Julian Houston
Now for a look at a book that examines the prep school life in a slightly different way.  New Boy is the story of Rob Garret a young man who leaves his home in Virginia to become the first African-American student at Draper, an elite Connecticut boarding school.   It is based on author Julian Houston's own experiences at the elite Hotchkiss School in Lakeville Connecticut.  Rob studies hard and boldly refuses to stereotype himself.  Although he himself encounters little racism, he is shocked when one of his friends is brutally bullied for his ethnicity.  Even more surprising to him is the fact that the school refuses to do anything about it or cross the offending students, who are very well connected.  Meanwhile. the civil rights movement is taking shape back in Rob's home territory of the South, which will present new challenges as the story takes shape.  Houston does a superb job representing the crosscurrents of the civil rights movement through his writing.



Prep - Curtis Sittenfeld
Another prep school alum pays tribute to her academy days in literary form in Prep.   In her novel, which offers a semester by semester tour of the elite Ault School, a fictional Massachusetts boarding school, Curtis Sittenfeld drew heavily on her days at the Groton School.  Such a story may sound familiar, as it is similar enough to that of John Knowles, who's experiences at Phillips Exeter Academy inspired his quintessential prep school novel A Separate Peace.  Although Prep lacks the "poetic angst" that Knowles wrote so well, her heroin Lee Fiora is similar enough to Gene, the hero of A Separate Peace.  Like Gene, she is an introverted adolescent who does not come from a family as wealthy as many of her classmates.  Much of the story consists of Lee's observations of the world of privilege around her, giving us an honest glimpse of what it is really like to be a scholarship student at a super-elite prep school.  Ault isn't quite as she imaged it would be, which goes to show us that maybe the prep school world of khakis and navy blue blazers isn't quite as we tend to imagine it either.

Honorable Mentions - 
The Keeper of Dawn - J.B. Hickman
Old School - Tobias Wolff (alum of The Hill School)
Gossip of the Starlings - Nina de Gramont
The Year of the Gadfly - Jennifer Miller

College Prep: The Preppiest Colleges in America, 2014.

If you search the internet for a list of the preppiest colleges in America, you'll mind many, many options.  Of the hundreds of thousands of colleges and universities in this country, the preppiest ones are generally found in the North and South.  Books such as The Official Preppy Handbook (our bible) have ranked the preppiest colleges in a specific, but we won't be doing that.  We will, however, provide you with a list of what are considered to be the preppiest colleges in American as of this year, 2014.

If you don't see your school and think it should be included, please comment with a reason as to why.

Hampden-Sydney College, VA

The Official Preppy Handbook dubbed Hampden-Sydney the peppiest college in the country, as did the Huffington Post.  It has been referred to as the "finishing school of southern gentlemen" and it is a general belief that single sex schools are always preppier than any co-ed university.  It should also be noted that HS is one of only four all male colleges remaining in the United States.  William Henry Harrison, our country's 9th president was a member of the class of 1791. HS students are known for sporting belts with their school's notable crest and it is said that they refer to themselves as "gentlemen."  This school has even gone so far as to publish their own etiquette guide titled From Manor Born to Manners Bred, which has even been updated for the digital media age.  If that doesn't say preppy, than I don't know what does.

Trinity College, CT
I've called the east coast the "bastion of preppy things," so of course it has many preppy colleges, but this one really does take the cake.  A small, private liberal arts school nestled in the heart of New England, it seems to have everything a prep school grad could want for.  The Official Preppy Handbook listed Trinity as one of the top 20 preppy colleges in America. True Prep also paid homage to this school, featuring a piece on a Trinity alumnus and his perfect wardrobe.  Trinity was all male until 1969 and has graduated many fine men and women, including Edward Albee and Tucker Carlson, both of whom are featured on our "Prepdom Hall of Fame."  Preppy Handbook and True Prep author Lisa Birnbach referred to Trinity as the "preppiest college in New England" which is definitely saying something.  Looking at that photo, it's easy to see why so many students choose to go to college in New England.  East coast represent!

Princeton University - NJ
Of course, no list of preppy school's would be complete without at least one representative from the Ivy League.  In his book The Making of Princeton University: From Woodrow Wilson to the Present, author James Axtell referred to the boat shoe (i,e the Sperry Top-Sider, the quintessential shoe of the New England prep school student) as a "notable symbol of Princeton."
If you didn't gather this from the book title, former U.S. president Woodrow Wilson was a Princeton alum.  A columnist for the Daily Princetonian said of Princeton "The manliest men wore the most pink and the girliest girls swooned at their sides."   New Jersey is also home to the elite Lawrenceville School, one of the most prestigious prep schools in the country, which has been described as "looking and acting like a mini Princeton."  It's also worth mentioning that the town of Princeton is home to stores such as J. McLaughlin, Palm Place, Ralph Lauren, J. Crew and many more, all of which are ideal for updating a preppy wardrobe.

University of Virginia, VA
Public and state schools don't tend to be preppy, but this flagship state university is certainly an exception.  When Thomas Jefferson couldn't get his alma mater, The College of William and Mary declared the official university of Virginia, he started his own and thus UVA was born.  It is one of the most selective public universities in the country and certainly the preppiest.  It's greek system is well known and while most colleges have "Greek Row" or something similar for their greek houses, UVA has Rugby Road.  The phrase "Guys in ties, girls in pearls," is a well known mantra around campus, but perhaps the most impressive preppy factor is this; At the nearby College of William and Mary, they have "dress like a UVA day" where all the students dress as preppy as they can, typically sporting pink and greek clothes with popped collars.  It really is impressive when a state school can manage to be more preppy than a prestigious private one.

Connecticut College, CT
You've read about Trinity College above, now meet their sister school, Connecticut College.  Located near the ocean in scenic, upscale Trinity went co-ed. The Official Preppy Handbook described it as being filled with students who were didn't get into Wesleyan or Brown so they retaliated by getting even preppier.  Conn has also been mentioned on "Mad Men" as well as in John Updike's novel "The Witches of Eastwick." Located in the very upscale New London Connecticut, this small, private school has been nicknamed "Abercrombie U."  While we don't consider Abercrombie to be a preppy brand, the message is clear.  Conn is known for it's teams excelling in sports such as tennis, field hockey, squash and sailing, all the preppiest sports, as well as for their equestrian program.  Founded in 1911 as an all woman's school, Conn remained single sex until 1969, the same year that

Boston College, MA
Dubbed the "capitol of New England," Boston is known for many things.  Since one of these things is old money, it makes sense that the preppy culture would be strong there, particularly in the upscale neighborhood of Chestnut Hill, where BC is located.  The students at this historic private college have been described as looking like a "walking J. Crew catalogue" which would make perfect sense, given the great clothing shops that line the streets of Boston.  BC upperclassmen joke that freshmen return from winter break while an entirely new wardrobe that "conforms more to the BC look."  Although we don't know this for sure, it is also said that whenever BC faceed off against BU (Boston University) in hockey, the BC student body would chant "safety school" repeatedly.  

St. Lawrence University, NY
This isolated NY liberal art school was ranked number 8 on the list of preppiest colleges by The Official Preppy Handbook.  Known for it's constantly stellar teams in soccer, lacrosse, and most all hockey, St. Lawrence has been described as a "boarding school on steroids." Greek life is popular at SLU.  So are ski weekends, as the campus isn't far from some great slopes in both Vermont and Canada.  As the Preppy Handbook stated "Everyone has a Norwegian sweater and a brother who made the olympic trials."  St. Lawrence wasn't named in the Huffington Post's list of Top Ten Preppiest Colleges, but many thought that it should have been.  When I asked a current SLU student I know if his school was preppy he replied "Yes, it really is.  You see a lot of pastels and popped collars."

College of the Holy Cross, MA
This college is definitely the sleeper as far as preppy schools go.  Both The Official Preppy Handbook and The Huffington Post failed to list it as one of the preppiest schools and we're still trying to figure out why.
Holy Cross is very much the Trinity College of Massachusetts, an insular private college located in a not-so-nice city (in their case, Worcester), but home to many beautiful, ivy covered buildings and white-bred, preppy students who are rumored to rarely mix with the outside world (although in a city such a Worcester you really can't blame them).  Contrary to what it's name might suggest, Holy Cross is not a religious school by any means and although it's campus is home to a beautiful church, no one is required to go.  As it is an exclusively undergraduate institution, almost all of their students go on to attend top graduate schools.   Despite it's reputation for stellar academics, Holy Cross has been described as "Analogous with a J. Crew. Catalog" and "A drinking school with an intelligence problem." Certainly sounds preppy enough for me.

Miami University, OH
You might not expect to see a public school from the midwest on a list of preppy schools, but here you go.  This "public ivy" is by far the preppiest college in the midwest and probably the preppiest public university, second only to UVA of course.  UMiami Ohio has long been referred to as "J. Crew U" due to the dress of many of the students, which seems to include pressed jeans, oxford shirts, polos, monogramed clothing and, of course, Sperry Top-Siders for everyone. Despite being located in Oxford Ohio, it was named Miami university due to the Miami Native American tribe that once inhabited the area.  In a student conducted survey in 2010, 85% of the students admitted to getting emails from J. Crew.  Although fellow state school Ohio State University has a line of school clothing available from preppy fashion giant Vineyard Vines, it doesn't top what J. Crew U has accomplished.

Georgetown University, Washington DC
As a prestigious, top-tier university located in our nation's capital, it seems only natural that Georgetown University would earn a place on this list.   This former catholic college is said to be inhabited by students who love the area's strong cosmopolitan flavor.  The Official Preppy Handbook referred to Georgetown as having a "southern feeling with a dash of diplomatic corps.  It added that lacostes and top-siders were a must.  The Huffington Post mentioned that at Georgetown, backpacks were almost a faux paux and socks were rarely worn because as everyone knows, no true prep would wear socks with Sperrys.  It comes as no surprise that Georgetown would have many notable alumni in the fields of government and politics (including former United States President Bill Clinton), but they get extra prep points for graduate Abdullah of Jordan, reigning king of the Kingdom of Jordan who attended the Deerfield Academy in Deerfield Massachusetts.

Honorable Mentions - 
Babson College
Bowdoin College
Colby College
Colgate University
College of Charleston
College of William & Mary
Duke University
Elon University
Hamilton College
Hobart & William Smith Colleges
Hollins University
Sweet Briar College
Sewanee: University of the South
Union College
Vanderbilt University
Wheaton College
Williams College

Prep Schools in the News: Durham Academy

As a native New Englander, I haven't always paid tribute to the South on this blog, but I have to give them credit for this.

Durham, South Carolina is home to the elite Durham Academy, a coed day school with roughly 1,100 students.  I'd never heard of them until recently, but now I'm glad I have.  During the recent blizzard, the south found themselves dealing with a crisis that we in the north like to refer to as "snow."  They likely don't get too many snow days typically, but when they did, the head of this school knew just what to do.  Check out the link to the video below.


http://gawker.com/watch-two-teachers-rap-their-schools-snow-closing-anno-1522038680?utm_campaign=socialflow_gawker_facebook&utm_source=gawker_facebook&utm_medium=socialflow

Prepdom Hall of Fame: The Preppiest People Throughout History

As we stated in previous posts, thoughough history, many of this countries best men and women attended private preparatory schools.  Not all of them stayed preppy afterewards, however.  Some, like Pete Seeger, chose to write folk songs while others aspired to greater things.  Those who never lost sight of what it truly means to be a prep were carefully selected to be a part of out Predom Hall of Fame.

As far as preppy dynasties go, there can be no greater example than the Kennedy family.
Patriarch Joseph Kennedy Sr. saw to it that his sons had the best of everything, including education.  Despite having to live in the shadow of his older brother Joe Jr. upon first arriving at Connecticut's Choate Rosemary Hall, John F. Kennedy (above, right), or Jack as he was known, quickly excelled at both academics and athletics.  Like his father and brother before him he attended Harvard University, and somehow found time to become a war hero before becoming president.  As a side note, it is a known fact that he shopped at Brooks Brothers.  A true prep if ever there was one.  His younger brother Robert (above, left) a graduate of Massachusetts's Milton Academy and Harvard University also earned his place in the hall of fame.
Had their older brother Joseph, also a Choate and Harvard alum not died too young in World War II, he doubtless would have had a future in politics as well.



Back when he was still known as Barry, Barack Obama attended the Punahou School in Honolulu Hawaii.  I'm sure how many elite prep schools there are in Hawaii, but it seems safe to say that Punahou is the most prestigious.  Having President Obama as a graduate certainly doesn't hurt their reputation.  He began his collegiate career at California's Occidental College, but transferred to Columbia University as a junior, from which he graduated.  After that, he enrolled in Harvard Law School and was made an editor of the Harvard Law Review.  By the end of his second year, he was president of the journal.  Not the last thing he'd become president of.  His wife, Michelle Obama is known for sporting cardigans from J. Crew, which means bonus prep points.




Here is a more detailed list of the Hall of Fame Members.  More will be added.

Edward Albee -
Prep School: Lawrenceville School (expelled), Choate Rosemary Hall
University: Trinity College
Went on to Become: Playwright; winner of the Tony Award for Best Play and Pulitzer Prize for Drama.  His plays include "Who's Afraid of Virginia Woolf" and "The Zoo Story."

Stephen Birmingham -
Prep School: The Hotchkiss School
University: Williams College
Went on to Become: Author of "Our Crowd," "The Grandees," and "Real Lace" and professor of writing at the University of Cincinnati.

Benjamin C. Bradlee -
Prep School: St. Mark's School
University: Harvard University
Went on to Become: Editor and Vice-President of the Washington Post.

George H.W. Bush -
Prep School: Phillips Academy Andover
University:  Yale University
Went on to Become: 41st President of the United States.

George W. Bush -
Prep School: Phillips Academy Andover
University: Yale University, Harvard Business School
Went on to Become: 43rd President of the United States.

Tucker Carlson -
Prep School: St. George's School
University: Trinity College
Went on to Become: Political News Correspondent and Conservative Commentator.

Stephen Colbert -
Prep School: Porter-Gaud School
University: Hampden-Sydney College (transferred), Northwestern University
Went on to Become: Emmy and Grammy award winning political satirist, writer, comedian, actor, and television host.

Buck Henry -
Pep School: Choate Rosemary Hall
University: Dartmouth College
Went on to Become: Academy Award nominated actor, writer, and film/television director.

John F. Kennedy -

Prep School: Choate Rosemary Hall
University: Harvard University
Went on to Become: 35th President of the United States

Jacqueline Bouvier Kennedy -
Prep School: Ms. Porter's School
University: Vasar College (transfered), George Washington University
Went on to Become: First lady of the United States.

Robert F. Kennedy -
Prep School: Milton Academy
University: Harvard University
Went on to Become: United States Attorney General and Democratic Party Presidential Nominee.

John Kerry -
Prep School: St. Paul's School
University: Yale University, Boston College Law School
Went on to Become: 68th United States Secretary of State and Democratic Party Presidential Nominee.

John Knowles - 
Prep School: Phillips Exeter Academy
University: Yale University
Went on to Become: Author of quintessential prep school novel "A Separate Peace."

Tucker Max
Prep School: Blaire Academy
University: University of Chicago, Duke University Law School
Went on to Become: Author of numerous bestselling memoirs, including "I Hope They Serve Beer in Hell."

Ogden Nash -
Prep School: St. George's School
University: Harvard University (dropped out)
Went on to Become: Nationally renowned writer and poet.

Barack Obama -
Prep School: Punahau School
University: Columbia University, Harvard Law School
Went on to Become: 44th President of the United States.

Frederick Law Olmsted -
Prep School: Phillips Academy Andover
University: Yale University
Went on to Become: Landscape architect who designed for Phillips Academy, Berwick Academy, Groton School, Lawrenceville School, Pomfret School, St. Albans School, and  Nobel and Greenough School.  He also did design work for many colleges and universities such as University of California at Berkeley, Brawn Mawr College, Colgate University, Cornell University, Denison University, Miami University (Ohio), Mount Holyoke College, Smith College, Stanford University, Trinity College, University of Rochester, Washington University, Wellesley College, and Yale University.


Curtis Sittenfeld -
Prep School: Groton School
University: Stanford University
Went on to Become: Author of quintessential prep school novel "Prep" as well as others.

Colson Whitehead -
Prep School: Trinity School
University: Harvard University
Went on to Become: Author of such renowned novels as "The Intuitionist" and "Sag Harbor."

Yes They Did! - 5 People Who You'd Never Think Were Prep School Alumni

The Prep School Pantheon is a somewhat extensive list and I don't blame you if you didn't take the time to read through the whole thing.  It includes some people who never outgrew the preppy image and others who are almost the opposite.  We've prepared a list of the most surprising people on the list.  Read on, but prepare to have your jaw drop.

Pete Seeger - Avon Old Farms School.
One of the most beloved and influential folk musicians on his generation, Seeger wrote many songs.  Although many of them, most famously "We Shall Overcome," are beautiful, timeless songs, they are about as far away from preppy as you can get.  Seeger is identified much more with the "hippie movement," although that is also partially due to all the work he did with artists such as Arlo Guthrie.  Seeger clearly didn't forget his education at the prestigious Avon Old Farms School of Avon Connecticut, though, as one of his songs was titled "What Did You Learn in School Today?"




Seth Macfarlane - Kent School
No, this is actually not a joke.  Seth Macfarlane, the comedic genius behind Family Guy, American Dad, The Cleveland Show and feature film Ted used to wear blazers and khakis to school.  A Kent native, Macfarlane later reveled in an interview that his mother had been a teacher at his alma mater.  Anyone familiar with Macfarlane's work will know that he is unquestionably a comedic mastermind, but even so, the irreverent humor that made Family Guy a success is far from classy and there's nothing remotely preppy about it, although Macfarlane did play off his own boarding school experiences when he sent character Chris Griffin to an elite boarding school known as "Morningwood Academy" in an episode that went on to spoof Dead Poets Society.


Steve Carrell - Middlesex School
Hard to believe that the 40 Year Old Virgin grew up a prep.  A native of Concord Massachusetts, he, like Macfarlane, attended his local private school, which happened to be among the most prestigious prep schools on the east coast.  According to The Hollywood Reporter, Carrell was a skilled hockey player who appeared in multiple school plays.  Not many prep school jocks also join the drama club, but Carrell has always been a talented guy.  After Middlesex, he attended Ohio's acclaimed Denison University.  His original plan was to become a lawyer, but fortunately for us, he chose acting instead.

Trey Anastasio - Taft School
Dubbed the "quintessential hippy band of the 20th century," Phish really is as far away from preppy as you can get, which is why we were so shocked to learn that frontman Ernest Joseph "Trey" Anastasio III is an alum of one of Connecticut's best prep schools, The Taft School to be specific.  It was there that he formed his first two bands, which were called Red Tide and Space Antelope.  During his time at Taft, he also met fellow songwriter The Dude of Life who helped pen such Phish hits as "Slave to the Traffic" and "Run Like an Antelope."  During Phish's first performance, which occurred during Anastasio's days at the University of Vermont, the hippie rockers used hockey sticks as mic stands...classic Vermont.

Stefani Germanotta (Lady Gaga) - Convent of the Sacred Heart
Here's something you probably didn't know - Lady Gaga attended the same posh Manhattan prep school as Paris and Nicky Hilton.  At first glance, Gaga seems like the very last person who would have attended a religious private school, particularly one with the name Convent of the Sacred Heart.  Her meat and bubble dresses don't exactly scream "catholic private school" and there's never been anything preppy about her songs.  I guess some people really do undergo complete transformations between high school and adult hood.  Learning to play the piano by ear at age 4, Gaga clearly had her smarts so it's a small wonder she was admitted to New York University, although she did not graduate, dropping out of school to pursue music full time, like so many musicians before her.