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.

The Prep School Pantheon

Preparatory schools, be they boarding or day, graduate hundreds of students each year.  Some date back hundreds of years, such as the Roxbury Latin School, which was founded in 1645.  It has been referred to as the "oldest boys school in North America."  Not all those who attend prep schools are necessarily preppy, though.  The list we've provided may surprise you.  To make for easier reading, we've divided the list into categories.  Read on.

Entertainment -

Trey Antastasio - Taft School, Watertown CT
Mike Birbiglia - St. Mark's School, Southboro MA
Elizabeth Berkely - Cranbrook Schools, Bloomingfield Hills MI (x)
Humphry Bogart - Phillips Academy, Andover MA
Joy Bryant - Westminster School, Simsbury CT
Paul Butterfield - University of Chicago Laboratory Schools, Chicago IL
Steve Carrell - Middlesex School, Concord MA
Chevy Chase - Dalton School, New York NY
Mary Chapin Carpenter - Taft School, Watertown CT
Glenn Close - Choate Rosemary Hall, Wallingford CT
Stephen Colbert - Porter - Gaud School, Charleston SC
Chris Collingwood - The Hill School, Pottstown PA
Buster Crabbe - Punahau School, Honolulu HI
David Crosby - Cate School, Carpinteria CA
Jamie Lee Curtis - Choate Rosemary Hall - Wallingford CT
Blythe Danner, George School, Newton PA

Ted Danson - The Kent School, Kent CT

Bette Davis - Cushing Academy, Ashburnham MA

David Duchonvy - Collegiate School, New York NY
Adam Duritz - Taft School, Watertown CT

Jane Fonda - Emma Willard School, Troy NY
Jodie Foster - Choate Rosemary Hall - Wallingford CT
Matthew Fox - Deerfield Academy, Deerfield MA
Stefani Germanotta - Convent of the Sacred Heart, New York City NY
Paul Giamatti - Choate Rosemary Hall, Wallingford CT

Jake Gyllenhaal - Harvard-Westlake School, Los Angeles CA
Maggie Gyllenhaal - Harvard Westlake School, Los Angeles CA
Larry Hagman - Trinity School, New York NY
Anne Heche - Francis W. Parker School, Chicago IL
Ed Helms - The Westminster Schools, Atlanta GA
Buck Henry - Choate Rosemary Hall, Wallingford CT

Hal Holbrook - Culver Academies, Culver IA

Linda Hunt - Interlochen Arts Academy, Interlochen MI
William Hurt - Middlesex School, Concord MA
Rashida Jones - Buckley School, Sherman Oaks CA
Warner Klemperer - Cate School, Carpinteria CA
Tom Lehrer - Horace Mann School, New York City, NY
Tea Leoni - Brearly School, New York NY
Alan Jay Lerner - Choate Rosemary Hall, Wallingford CT
Huey Lewis - Lawrenceville School, Lawrenceville NJ
Lisa Loeb - Hockaday School, Dallas TX
Stacy London - Trinity School, New York City NY
Jon Lovitz - Harvard-Westlake School, Los Angeles CA
Seth Macfarlane - Kent School, Kent CT
Roger McGuinn - Latin School of Chicago, Chicago IL
Elizabeth Montgomery - Spence School, New York City NY
Frank Morgan - Trinity School, New York NY
Oliver Platt - Colorado Rocky Mountain School, Carbondale CO
Cole Porter - Worcester Academy, Worcester, MA

Keshia Knight Pulliam - Foxcroft School, Middleburg VA
Chris Raab - Church Farm School, Exton PA
Bonnie Raitt - Oakwood Friends School, Poughkeepsie NY
Christopher Reeve - Princeton Day School, Princeton NJ
Kyra Sedgwick - Friends Seminary, New York NY
Pete Seger - Avon Old Farms School, Avon CT
Wallace Shawn - Putney School, Putney VT
M. Night Shyamalan - Episcopal Academy, Newton Square PA
Stephen Sondheim - George School, Newton PA
James Spader - Brooks School, North Andover MA
James Stewart - Mercersburg Academy, Percersburg PA

Sufjan Stevens - Interlochen Center for the Arts, Interlochen MI

Stephen Stills - Admiral Farragut Academy - Pine Beach, NJ

James Taylor - Milton Academy, Milton MA
Gene Tierney - Miss Porter's School, Farmington CT

Justin Theroux - Buxton School, Williamstown MA

Uma Thurman - Northfield Mt. Hermon School, Northfield MA

Rufus Wainwright - Milbrook School, Milbrook NY
Joss Wedon - Riverdale Country School, New York City NY
Carnie Wilson - Oakwood School, Los Angeles CA
Reese Witherspoon - Harpeth Hall, Nashville TN
Jeffrey Wright - St. Alban's School, Washington D.C.
James Van Der Beek - Cheshire Academy, Cheshire CT

Literature -

Edward Albee - Choate Rosemary Hall, Wallingford CT
Louis Auchincloss - Groton School, Groton MA
Dan Brown - Phillips Exeter Academy, Exeter NH
William F. Buckley Jr. - Millbrook School, Millbrook NY
Truman Capote - Dwight School, New York City, NY
John Dos Passos - Choate Rosemary Hall, Wallingford CT
T.S. Eliot - Milton Academy, Milton MA
F. Scott Fitzgerald - Newman School, Hackensack NJ
John Green - Indian Springs School, India Springs Village AL

John Irving - Phillips Exeter Academy, Exeter NH

Jack Kerouac - Horace Mann School, New York NY
John Knowles - Phillips Exeter Academy, Exeter NH
Tucker Max - Blair Academy, Blairstown NJ
Bill Matthews - Berkshire School, Sheffield MA

Margaret Mitchell - Washington Seminary
Odgen Nash - St. George's School, Middletown RI

Edward Said - Northfield Mt. Hermon School, Northfield MA
Aram Sayoyan - Trinity School, New York City NY

Curtis Sittenfeld - Groton School, Groton MA
William Stryon - Christchurch School, Christchurch VA

Gore Vidal - Phillips Exeter Academy, Exeter NH
DeWitt Wallace - Northfield Mt. Hermon School, Northfield MA
Thornton Wilder - Thacher School, Ojai CA (x)
Colson Whitehead - Trinity School, New York NY
William Carlos Williams - Horace Mann School, New York City NY

Richard Yates - Avon Old Farms School, Avon CT

Business -

S. Prestly Blake - Northfield Mt. Hermon School, Northfield MA
Ivan Boesky - Cranbrook Schools, Bloomingfield Hills MI (x)
Benjamin Crowninshield Bradlee - St. Mark's School, Southborough MA
Jamie Dimon - Browning School, New York City, NY
Tom First - Concord Academy, Concord MA

Steve Forbes - Brooks School, North Andover MA
William Randolph Hurst - St. Paul's Preparatory School, Concord NH

Richard Mellon Scaife - Deerfield Academy, Deerfield MA
George Steinbrenner - Culver Academies, Culver IA
Donald Trump - New York Military Academy, Cornwall-on-Hudson NY
Ted Turner - McCallie School, Chatanooga TN

Mark Zuckerberg - Phillips Exeter Academy, Exeter NH

Politics -

Howard Baker - McCallie School, Chatanooga TN
George Herbert Walker Bush - Phillips Academy Andover, Andover MA
George Walker Bush - Phillips Academy Andover, Andover MA
Peter Fisher - Concord Academy, Concord MA
John Fitzgerald Kennedy - Choate Rosemary Hall, Wallingford CT
Robert Francis Kennedy - Milton Academy, Milton MA

Edward Kennedy - Milton Academy, Milton MA

Jacqueline Bouvier Kennedy Onassis - Miss Porter's School, Farmington CT (although not a politician herself, she was known for being married to one)

John Kerry - St. Paul's School, Conchord NH
John McCain - Episcopal High School, Alexandria VA
Barack Obama - Punahau School, Honolulu HI
Deval Patrick - Milton Academy, Milton MA
Mitt Romney - Cranbrook Schools, Bloomingfield Hills MI
Franklin Delano Roosevelt - Groton School, Groton MA
Eliot Spitzer - Horace Mann School, New York City NY

Daniel Webster - Phillips Exeter Academy, Exeter NH

Other -
Josephine Patterson Albright - Foxcroft School, Middleburg VA
Tina Barney - Spence School, New York NY
Stephen Birmingham - Hotchkiss School, Lakeville CT
Judge Robert Bork - Hotchkiss School, Lakeville CT

Tucker Carlson - St. George's School, Middletown RI

Roy Cohn - Horace Mann School, New York City NY
Anderson Cooper - Dalton School, New York City, NY
Joseph Cornell - Phillips Academy Andover, Andover MA
Daniel Ellsberg - Cranbrook Schools, Bloomingfield Hills MI
Buckminster Fuller - Milton Academy, Milton MA
John Lahr - Riverdale Country School, New York City, NY
Sally Mann - Putney School, Putney VT (photographer)
Dr. William H. Masters - Lawrenceville School, Lawrenceville NJ
Bill Nye - Sidwell Friends School, Washington D.C.
Keith Oblermann - Hackley School, Tarrytown NY
Georgia O'Keeffe - Chatam Hall, Chatam VA
Frederick Law Olmosted - Phillips Academy Andover, Andover MA
Princess Leila Pahlavi - Rye Country Day School, Rye NY
James Pierpont - Roxbury Latin School, Roxbury MA
Zac Posen - Saint Ann's School, New York City NY

John Silas Reed - Morristown School, Morristown NJ
Sally Ride - Harvard - Westlake School, Los Angeles CA
Chris 'Mad Dog' Russo - Darrow School, New Lebanon NY
Ilyasah Shabazz - The Masters School, West Simsbury CT
Dr. Benjamin Spock - Phillips Academy Andover, Andover MA
Elizabeth Cady Stanton - Emma Willard School, Troy NY
Vera Wang - Chapin School, New York NY

(x) = did not graduate

**more to come

The Silver Screen - Prep School Films

Over the years, Hollywood has often tried to capture the prep school essence on film.  While some of these films are cinematic masterpieces, others fall short.  Often, prep schools and their students are portrayed a certain way  on the silver screen.  Is it accurate?  You be the judge.  There have been numerous preppy films over the years and we can't review them all, but here are, in my opinion, the top four best prep school films to date.  Prep or not, each film comes highly recommended.

My favorite film to date is Dead Poet's Society.  It really is the ultimate prep school film, complete with privileged white kids, a pretentious, stuffy school headmaster, blowhard parents, and even an underdog triumph or two. 

Set in the 1950's, the story begins at the prestigious, conservative Welton Academy (a fictional Exeter), an all white, all boys prep school in Vermont.  It is an age of cheerless conformity until Mr. Keating (Robin Williams), a Welton alum returns to teach English.  Wanting the boys to learn to think for themselves, he inspires them make their lives extraordinary with the iconic phrase "Carpe Diem, Lads."  Such boys as Keating's students are prone to society telling them what they could and couldn't do.   As the story unfolds, the boys learn to take chances, face their demons (or in some cases, their parents) and above all, lead happy lives.  While there are some unquestioningly sad moments, this truly is one of the greatest films ever made.  The final scene could bring a tear to a glass eye.  Absolutely worth a watch.  Every school needs a teacher like Mr. Keating.  I certainly wish my prep school could have had one.

 Second on the list is a somewhat underrated adolescent drama known as The Emperor's Club.  Kevin Kline stars as a passionate history teacher at the fictional St. Benedict's School, another posh, New England prep school.  Like Mr. Keating, he wants to inspire his students to lead extraordinary lives and asks them "How will history remember you?"  Everything seems to be going well until a new student joins his class.  Sedgewick Bell (Elijah Wood) is the son of a U.S. senator and your classic spoiled rich kid.  Smart, but cocky and rebellious he immediately stirs up trouble wherever he goes.  Kline vows to help the boy, but he soon realizes he may have his work cut out for him and that's where the movie gets interesting.  There are definitely some similarities to Dead Poet's Society and some have even gone so far as to call this movie a rip-off, but they are by no means the same film. Watch them both and you will seen the distinctive differences.  Also appearing is a teenage Jessie Eisenberg, before he got to Harvard, who costars as one of Sedgewick's friends.  For the millions who loved Dead Poet's Society, this film is definitely worth watching.

The next film on our list has a slightly darker, certainly more dramatic feel.  School Ties was also set in the 1950's, but unlike Dead Poet's Society, it pays homage to the times in a different way; tackling racism and prejudice   Brendan Frasier stars as David Green, a working class, jewish teen from Scranton PA who is awarded a football scholarship to the prestigious St. Matthew's Academy in Massachusetts.  The posh New England world is far removed from the working class mill town where he grew up and David is forced to hide his jewish roots from his wealthy, sometimes arrogant and bigoted classmates.  That said, he bonds well with them and becomes a football star.  Everything is going great until he mistakenly crosses his wealthiest classmate and trouble instantly follows, forcing David to consider who he is, what he wants, and what he stands for.  The film is stolen by Matt Damon, who stars as Charlie Dillion, the arrogant, wealthy head boy who's stoplight David steals without meaning to.  Dillion, the film's antagonist, is the classic New England prep school jerk; wealthy and arrogant with no concern for the less fortunate and willing to screw anyone over to get what he wants. Also appearing are Ben Affleck and Chris O' Donnel, who appear as classmates of David and Charlie.  School Ties may make you reconsider sending your kids to a New England prep school, but this film does not accurately portray such schools in current times.  There is some racism and anti-seminism displayed, but if that sort of thing doesn't bother you, it's definitely worth a watch.  There are some strong messages about friendship and loyalty.

Our final film on the list is one of the only prep school comedies, at least to my knowledge.  Outside Providence is the story of Tim, a working class kid from blue collar Providence Rhode Island.  He's happy stirring up trouble with his friends and causing havoc wherever he goes, but when he damages a police car, he's finally gone too far.  His father (Alec Baldwin) is a working class, beer swilling jerk, but when Tim crosses a line, he decides to send him to a posh boarding school where he can't get into trouble.  How a blue collar working can afford to put his kid through an expensive private school is never explained, but from there the film gets interesting.  Tim doesn't meet the same fate as David Green, as his film is set in a different era.  In fact, his story is much funnier, although there are a few tender moments.  Along his journey he falls in love and learns about a new way of life.  This film doesn't have the emotional depth of Dead Poet's Society or the life lessons of School Ties, but it's a good watch, particularly if you like to laugh.

Honorable mentions -
Six Degrees of Separation
Igby Goes Down
Goodbye, Mr. Chips.

Preppy Footwear

Of course, no outfit is complete without proper footwear.  I've decided to provide a list of the best preppy shoes.  Different shoes go with different outfits and colors, but the best kinds are the ones that will go with most anything.

 The ultimate preppy shoe will always be the top-sider boat shoe, made famous by Sperry (pictured left).  There have been many cheap knock offs such as Island Surf, but Sperry's are the real top-siders.  Their classic brown color means they can go with just about any outfit, be it formal or casual, although too formal will warrant something more dressy, such as wingtips.  They were originally designed to be worn on boats.  It stands to reason that if your dad just spent half a million dollars on a boat, he's not going to want you marking up the deck with your shoes.  Thanks to the non-marking souls of top-siders though, that problem has ceased to exist.  They come in many colors, but with shoes like these, you really can't go wrong.  Sperry's can even be found at J Crew, a store that doesn't always carry products from different labels.

H.G. Bass also features a line of good boat shoes, but their most notable creation is the Weejun Penny Loafer (pictures right).  Although more formal than top-siders, Weejuns can also go with most outfits, although black may be too formal for casual occasions.  Brown weejuns tend to go better with most things.  These shoes come in many colors and patterns, from the classic solid colors such as brown and black to more daring patterns such as stripped, denim, or even plaid.  Plaid weejuns are great shoes (I own a pair myself) although they can be difficult to match with certain shirts and pants or shorts.  That said, If you want an eye catching shoes, there's no better model out there.  Anyone who ever watched "Mr. Rogers" may recall that the star of that shoe wore Penny Loafers.  These shoes were popular in the 1970's but thanks to Bass, their making a come back.  As a side note, if you walk around with an actual penny in the front compartment, it won't fall out.  I know from experience.  The ultimate formal shoe will always be the wingtop, though.

Of course, some occasions call for sneakers, and that's where Keds come in.  These shoes were popular in the 1940's and afterwards, but now their making, or have made a comeback, which is great.  Keds look good, and their comfortable, fine for most casual athletic activity.  Vans, which are similar to Keds and come in more colors, are also acceptable, and they are
even available at J Crew (pictured below).

Preppiest Clothing Brands and Labels

They say the clothes make the man (or the woman), and in the preppy culture, that's certainly true.  The way someone dresses is typically the first indication of weather or not they are preppy.  That is not to say that everyone who wears an oxford shirt, a navy blue blazer, or nantucket reds is a prep, but just about any and all New England preps tend to dress in a similar fashion and it is very upscale.  Almost all prep schools that don't have the word "waldorf" in their title have uniforms that require ties, so all prep schools students learn to dress themselves in high school.  As many are at boarding school, they have to.  Different clothing brands cultivate different images and just because something is expensive doesn't mean it's preppy (i,e Abercombie & Fitch).  The classic clothing brands, though, will always cultivate a strong, preppy aire.

Ralph Lauren is very likely the most popular clothing brand in the field of preppy clothing.  They perfected the polo shift and all their clothes are top-notch, expensive as they many be.   All their shirts, like the one pictured below, are classic preppy, be they oxford, polo, henley, or even athletic apparel.  Their pants, of course, all the various chinos, kakkis, and even denim are top of the line and they also feature great shoes of all types, from loafers to boat shoes to sandals and flip-flots.  Plenty of preppy accessories to, such as pocket squares, keychains, and baseball caps.  At a store like Ralph Lauren, really anything is preppy.  Their polo player logo is an absolute preppy icon.

If you want to talk preppy though, Brooks Brothers you really can't beat Brooks Brothers.  Brooks Brothers features all the same clothes as Ralph Lauren, and even goes beyond with their items such as Cricket Vests (classic old school preppy) and books on how to be a gentlemen at the counter.  As great as their clothing is, though (I particularly find their sweaters to be especially comfortable), Brooks Brothers went above and beyond as far as preppy goes, when they laughed their "Great Gatsby Collection" in May 2013, prior to the release of the film.  They also began carrying copies of the book in store.  As expensive as this line was, for any Fitzgerald buff or just any preppy aficionado in general, they really are a must have.   I think the picture below will explain why.

I mean, seriously, who wouldn't want to be seen wearing that red and white stripped regatta blazer?  The brown and white wingtips tempted me as well.  Their clothes are absolutely fantastic and you don't have to be a Brooks Brothers model to pull them off...you just have to be Jay Gatsby himself in order to afford them  (It's worth mentioning that F. Scott Fitzgerald himself, one of the greatest preppies to have ever lived, shopped at Brooks Brothers in his day). Gatsby had all his shirts send to him from England, but if you can't work that, Brooks Brothers isn't a bad alternative, at all.  There can be no question that this is the sort of clothing Gatsby would have worn.  People then (at least in West Egg) had such great fashion taste.  Why couldn't I have grown up in that era?

Ralph Lauren and Brooks Brothers are just two of the many preppy brands our there.  That said, it is important to know which one as classic preppy and which ones are new wave pretenders.  J Crew and Lacoste should also be acknowledged.  Lacoste may not be quite as formal as Ralph Lauren or Brooks Brothers, but their clothing is great.  Their polos are top-notch and their logo, the signature alligator (pictured right) is as well known as the Ralph Lauren polo player.  J Crew may have a slight new wave/almost hipster (shudder) edge to it, but the edge is very slight and their clothing is more formal than Lacoste.  Their chinos, which come in just about every different color, are fantastic, and they produce perhaps the most comfortable v-necks.  Banana Republic deserves an honorable mention, as does Vineyard Vines.  Nantucket Reds will always be the ultimate preppy pants though.  The beautiful island of Nantucket (a popular vacation spot for wealthy new englanders i,e a preppy stomping ground in the summer) is home to Murray's Toggery Shop, where the original Nantucket Reds can be found.  It doesn't get any more authentic than that.  Don't be fooled, though.  Brands such as Land's End and Eddie Bauer are NOT preppy, as similar as their clothes may be to those you'd find at L.L. Bean.  Avoid brands such as Abercrombie & Fitch, American Eagle Outfitters, and Aeropostale...that's frat boy attire, and not the kind of frat a true prep would join.

Top Men's Preppy Clothing Labels (not ranked in order)
Ralph Lauren
Brooks Brothers
J. Crew
Lacoste
Vineyard Vines
Banana Republic
J Press
York Street
Tommy Hilfiger
G.H. Bass
L.L. Bean
Barbour
Smathers and Branson

For Footwear
Sperry
G.H. Bass
L.L. Bean (for their signature Duck Boots)

Honorable Mention
Nantucket Brand
The Gap
Tuckernuck
Van Heusen
U.S. Polo Association (USPA)


Brands to Avoid
Abercrombie & Fitch - We all know how CEO Mike Jefferies feels about large or "ugly" as he calls them, people buying his clothes.  Multiple lists of reasons not to shop there can be found here - http://www.huffingtonpost.com/news/mike-jeffries

Hollister - Abercombie's ugly cousin...and the surfer clothing is very west coast...notice how their website is divided into "Dudes" and "Bettys" and all their colons are named after places in Southern California.

American Eagle Outfitters - Thinly, cheaply disguised Abercrombie clothing.

Aeropostale - A poor man's American Eagle.

Land's End - A poor man's LL Bean.

Eddie Bauer - Decent chinos, but that's it as far as clothing goes.  Good for outdoor supplies, though.

The East Coast Prep

As a lifelong native of a wealthy Massachusetts "money town," and a prep school student alumn, I know full well that the east coast, more specifically New England, is the bastian of the classic American preppy culture.  No disrespect to the west coast, but as far as preppy goes, it simply can't compete with the east.  Let's look at some facts.

The term "prep" comes from the word, preparatory, and refers to someone from a college preparatory school.  Every true prep comes from, or came from a private college preparatory school and the east coast can only be described as America's prep school hotbed.  When thebestschools.org listed "The 50 Best Private Day Schools in the United States, 8 out of the top 10 were located on the east coast.  Congratulations to New York's The Trinity School for being voted number one.  For the complete list see the following link.  http://www.thebestschools.org/blog/2013/04/30/50-private-day-schools-united-states/.

Trinity is only one, though.  The Kennedy family has been described as the "truest American royalty," and former president John F. Kennedy, the most notable member, is an alum of Connecticut's Choate Rosemary Hall (pictured), arguably one of the most prestigious prep schools not just on the east coast, but in the country. Before that, he attended the Riverdale Country School, a very highly respected all boys prep school in New York City.  Before John arrived at Choate, his elder brother Joseph Kennedy Jr. attended and was a star football player as well as a leading student before attending Harvard University.  In his senior year, John was voted "most likely to succeed.  I think it's safe to say that when his classmates voted for him, they made the right choice.  It is worth mentioning that Kennedy attended private schools all through his academic career, starting with Brookline's The Edward Devotion School and ending, of course, with Harvard University, like all the other Kennedy men.  His younger brother, Robert Kennedy, who almost became president and served as John's attorney general, attended Milton Academy in Massachusetts (pictured).  Like his brothers before him, he too attended Harvard University.

Suffice it to say, the wealthy and powerful Joseph Kennedy Sr, who could could have sent his many children anywhere in the country, was a steadfast supporter of prep schools.  It clearly had it's merits, though, when you consider how successful his sons were later on in life, tragedy aside.

In later posts, we'll discuss the east coast more and just what makes it the preppy bastian that it is.  The private schools, the colleges, the vacation spots, the styles, and just about everything in between.   The east coast really does have it all, and if you keep reading, you'll see.