This Week in Connecticut: Preppy Handbook turns 45
July 27, 2025
The Official Preppy Handbook was first published in 1980. It defined fashion at the time and still impacts style today.
Dennis House, Chief Political Anchor and Host of “This Week In Connecticut” on WTNH News 8, an ABC affiliate, chatted with Matthew Longcore, the founder of the Preppy Handbook Fan Club and the publisher and editor of Ivy Style.
Matthew is wearing a navy blazer from J. Press and madras pants from Duck Head.
I remember well TOPH from my college days. Several copies made their way through my fraternity. I finally purchased a copy. Gifted it to our son when he pledged my old frat.
Mark, which college and fraternity? My alma mater, Trinity College, is listed in TOPH
and two fraternities at the college are mentioned, Psi Upsilon and St. Anthony Hall.
Matthew, a small state college in Mississippi, Delta State. I was a KA as well as my son. We both went on to other schools for terminal degrees. Congrats on your Ph.D.
Matthew: I enjoyed your TV interview regarding the Preppy Handbook and fan club. But I could not help having a chuckle when you said the oldest item of preppy clothing you own today is a pair of Sperry Topsiders which you have had more than a decade. I hope you do not think less of me, but with the exception of underwear, socks, three or four OCBD’s, a few ties, and a reasonably new navy 3/2 sack suit I purchased from O’Connell’s for my daughter’s wedding, everything I own is older than a decade. I have two ties I still wear that I bought when I was in college sixty years ago. And all my sport coats were purchased from H. Stockton in Atlanta before we moved to North Carolina in 1987. Regards, JHG
Hank, your wardrobe certainly makes mine look new. I have to correct myself on the shoes. They are Sperry CVOs, not Topsiders. After many sailing seasons, the salt washed navy blue has faded to a nice blue grey, much in the same way that my Nantucket Reds have faded to a salmon pink. Canvas sneakers can last forever, but I am not sure if this is true for leather Topsiders. They need to be replaced quite often, in my experience.
If deck shoes go on an actual boat in salt water, they’re not going to last long. My beat-up pair leech salt almost as quickly as my body sweats booze when I get home from a fishing trip on the Texas coast.
The blue and white stripes of the tie and the watchband are for Yale. Actually the Yale watch was a graduation gift from my father when I received my M.A. in 2018. I do like the sockless look for loafers, but socks seemed appropriate for suede bucks on television.
Although the OPHB was satire, it pretty much nailed Ivy and its progeny, early prep. I daresay most men here still dress pretty much as the book suggested. The mode of dress for women, however, has changed pretty radically. As the thinking world backs off from fast fashion and re-embraces natural fibers, I wonder how women’s clothing will change.
Tim, your observation about the Official Preppy Handbook is spot on. The handbook’s descriptions of men’s clothing continue to provide a veritable blueprint for classic Ivy. For menswear, we have witnessed a certain degree of immunity to trends. In contrast, women’s clothing as described in the handbook has not withstood the test of time. Fashion and fad play a much larger role for womenswear than for menswear. I can recall many conversations with women over the years ago have said, “oh I love the preppy look for men, but not for women.” The subtext is that the androgynous aspects of the so-called preppy style described in the Official Preppy Handbook lack femininity.
Really glad I picked up a great condition copy on eBay a year or two ago for $50 bucks. The only wear on it is the inside cover which says: “To my Preppy Dad … Christmas 1980”. Pretty neat.
The emphasis on underdressing doesn’t receive the attention it deserves. Addendums to this philosophy are understatement and subtlety. My favorite men’s stores (R.I.P.) stocked a wee bit of madras, but the tartans were solid (not patched) and quite intentionally muted. Seersucker wasn’t nearly as popular in the South as exaggerated, imagined mythologies would have us believe. Poplin (tan, taupe, olive) and worsted panama (especially “Cambridge Gray”) were key for summer. I don’t recall anybody wearing bright pink or lime green, but Charleston Red was an option for club dinners. Lilly Pulitzer was more Florida Palm Beach than Southern Ivy. The most flamboyant items in most Southern natural shoulder wardrobes were glen checked tweed jackets, pale yellow oxfords, and tasseled mocs.
Your recollection and mine are almost identical. The more colorful items associated with prep were simply not part of collegiate/Ivy dressing. I did not see patchwork Madras until the 1970s. The Madras jackets you saw at school in late spring and early fall were in a palette not that different than the tweeds. I remember pale blue pin-cord in Virginia summers but not much seersucker. The first deviation from subtlety that I recall was when larger paisleys arrived around the time of Carnaby Street. Shirt colors now widely accepted such as light green and lavender were non-existent. Pink was present in Virginia but unusual.
Samuel, I agree with you wholeheartedly about the importance of understatement. I do believe that it is the pinnacle of Ivy Style. Once we veer off into being ostentatious, we have lost the basic ethos of the style.
S I You talked about poplin suits in your comments I can remember in 1961 while I was in boarding in MA my parents taking me to see Charlie at the Andover shop in Cambridge and buying me a tan poplin suit . I think it was either a Haspel or Deansgate and a gant shirt for $75.00. The great thing about the tan poplin suit was that you could wear it as a suit or just the jacket with a pr. of summer gray flannels or just wear the tan pants.
A lot has happened since the original OPH was published. The Reagan era, accompanied by the 80s “Greed is good” mentality, and the Bush-Clinton-Bush era, when/where Yuppieism and Boboism (see David Brooks book) flourished. The Old Guard Liberal Establishment, including moderate and progressive Republicans, breathed their last breath (see Chris Hedges book), and the gap between middle-class Americans and the rich widened drastically. Even more comic/tragic is the gap between the rich and the super rich. This constitutes a problem for anyone who favors the sartorial excesses of “Preppy.”
There are reasons to guess old-fashioned Heyday era Ivy, subtle and understated (if slightly staid), will thrive as a form of vintage Americana. Cause for celebration. But “Preppy” will continue to decline. I can’t imagine a scenario where the sartorial totems of upper-class leisure are welcomed and embraced by a majority. Stated more bluntly: in thirty years there will be no market for patch madras or embroidered whales, lobsters, and tennis racquets, and retailers who’ve peddled pink-dyed canvas clothing will wring their hands anxiously.
The style many of us appreciate, an American take on certain British goods, wasn’t born in New York or an entrepreneurial New Haven tailor’s office. The market for the flannel, challis, oxford, and tweed preceded the marketing, which means an already existing culture inspired its introduction to an American audience. That culture, the Liberal/Mainline Protestant Establishment, has been dying slowly yet surely since the 70s. Deemed quaint and useless (Cy Vance and Sarge Reynolds were paragons) by the more radical elements of American society, the fade has been steadfastly constant.
There are still a few remaining corners and crevices, but they’re few in number and hidden (hiding out, actually) and languishing. J. Press was saved by a Japanese retail giant (a hobby for a few Japanese “trads”) and honesty demands that O’Connell’s, the only remaining Ivy outpost, will not expand operations anytime soon. A safe guess is both have persevered only because of the online sales.
Business school 101: A culture creates a market. When the culture dissipates and dies, the market, gasping for air, follows the slumber to the grave. Digby Baltzell predicted hopefully that American patricians would teach the rest of us how to invite and practice their long-held values, including discretion, generosity of spirit, noblesse oblige, proper manners, and kindness.
I admire his optimism, but he was wrong. America is not the “kinder, gentler nation” with which the Old Guard Liberal Protestant Establishment was entrusted. Their stewardship, honorable and noble, was overwhelmed and vanquished by instincts and values that will fail us. The brash, hyper macho aesthetic, whether dressed up or t-shirted and denim’s, is as descriptive of the American soul — and prescriptive for anxious, fearful people who feel lost.
Samuel, thank for your eloquent and well stated commentary. I appreciate the reference to E. Digby Balzell, a true gentleman scholar. Baltzell inspired my career in academia, and references to his work feature prominently in my doctoral dissertation. Here is a quick story you might appreciate. A year or so after I graduated from Trinity College, I decided to reach out to Baltzell via a phone call. I used a certain black and orange social directory to obtain his phone number. This of course was the pre-Internet era of land lines. Baltzell was a bit gruff at first, not pleased that some stranger had contacted him while he was watching a Philadelphia Eagles game. I explained that I admired his work and he was profoundly influential for me. That seemed to soften him a bit and we proceeded to discuss a variety of matters. I told him that I had just recently graduated from Trinity College, but had applied to the University of Pennsylvania as a transfer student and almost went, but decided to stay at the small liberal arts college for fear I might get lost at the larger university. “Trinity is a good school,” he said, “I know several graduates.” But then he added, “Penn is better. You should have gone there.” I felt at that moment he may have been right. Penn is excellent, and I could have taken classes with Baltzell, which would have been the opportunity of a lifetime. However, I must say, I am glad I stayed at Trinity. Ironically, my experience at Trinity was the starting point for my path to running Ivy Style as well as my interest in collegiate architecture. Nonetheless, I am glad that I connected with Baltzell that one memorable time. May he rest in peace.
Off topic, I guess, but I need to know. There is a noticeable lump in your right hand shoulder. I have one just like it on one shoulder on one of my mtm, H. Freeman sack suits, which I complained about, here, last week.
Crux: Why on earth do manufacturers insist on doing this? It seems so unnecessary. I’m not in the business, so I don’t understand. Wouldn’t the logical default position be to just leave that out? Then, if the customer really wants a lump in one shoulder, wouldn’t he ask for it?
How about that — you spoke with Baltzell. Lucky you. I would have lacked the courage to pick up the phone and dial.
Your decision to avoid undergraduate life in Philadelphia and remain at Trinity was very wise. I’ll leave it there, but, when it comes to temperament/persona of alums, Trin trounces Penn.
The Official Preppy Handbook was first published in 1980. It defined fashion at the time and still impacts style today.
I remember well TOPH from my college days. Several copies made their way through my fraternity. I finally purchased a copy. Gifted it to our son when he pledged my old frat.
Mark, which college and fraternity? My alma mater, Trinity College, is listed in TOPH
and two fraternities at the college are mentioned, Psi Upsilon and St. Anthony Hall.
Matthew, a small state college in Mississippi, Delta State. I was a KA as well as my son. We both went on to other schools for terminal degrees. Congrats on your Ph.D.
Thank you, Mark. KA is a great fraternity. At Trinity we had PKA, or Pike, also founded in the South at the University of Virginia.
Matthew: I enjoyed your TV interview regarding the Preppy Handbook and fan club. But I could not help having a chuckle when you said the oldest item of preppy clothing you own today is a pair of Sperry Topsiders which you have had more than a decade. I hope you do not think less of me, but with the exception of underwear, socks, three or four OCBD’s, a few ties, and a reasonably new navy 3/2 sack suit I purchased from O’Connell’s for my daughter’s wedding, everything I own is older than a decade. I have two ties I still wear that I bought when I was in college sixty years ago. And all my sport coats were purchased from H. Stockton in Atlanta before we moved to North Carolina in 1987. Regards, JHG
Hank, your wardrobe certainly makes mine look new. I have to correct myself on the shoes. They are Sperry CVOs, not Topsiders. After many sailing seasons, the salt washed navy blue has faded to a nice blue grey, much in the same way that my Nantucket Reds have faded to a salmon pink. Canvas sneakers can last forever, but I am not sure if this is true for leather Topsiders. They need to be replaced quite often, in my experience.
The link didn’t appear, so here it is:
https://youtu.be/nc1kXAnrlX4?si=mXmEGDymiaW6hFaV
Thank you for sharing the YouTube link. I have added it to the post.
If deck shoes go on an actual boat in salt water, they’re not going to last long. My beat-up pair leech salt almost as quickly as my body sweats booze when I get home from a fishing trip on the Texas coast.
Fun! 🤩 I like the tie-watchband combo. Thank you for wearing socks. I remember TOPH was stocked at the register at the bookstore in Fall 1980.
The blue and white stripes of the tie and the watchband are for Yale. Actually the Yale watch was a graduation gift from my father when I received my M.A. in 2018. I do like the sockless look for loafers, but socks seemed appropriate for suede bucks on television.
Nice to see you on TV!
Thank you! It was thrill to be interviewed on television.
Although the OPHB was satire, it pretty much nailed Ivy and its progeny, early prep. I daresay most men here still dress pretty much as the book suggested. The mode of dress for women, however, has changed pretty radically. As the thinking world backs off from fast fashion and re-embraces natural fibers, I wonder how women’s clothing will change.
Tim, your observation about the Official Preppy Handbook is spot on. The handbook’s descriptions of men’s clothing continue to provide a veritable blueprint for classic Ivy. For menswear, we have witnessed a certain degree of immunity to trends. In contrast, women’s clothing as described in the handbook has not withstood the test of time. Fashion and fad play a much larger role for womenswear than for menswear. I can recall many conversations with women over the years ago have said, “oh I love the preppy look for men, but not for women.” The subtext is that the androgynous aspects of the so-called preppy style described in the Official Preppy Handbook lack femininity.
Really glad I picked up a great condition copy on eBay a year or two ago for $50 bucks. The only wear on it is the inside cover which says: “To my Preppy Dad … Christmas 1980”. Pretty neat.
That’s a great find. Love the inscription.
The emphasis on underdressing doesn’t receive the attention it deserves. Addendums to this philosophy are understatement and subtlety. My favorite men’s stores (R.I.P.) stocked a wee bit of madras, but the tartans were solid (not patched) and quite intentionally muted. Seersucker wasn’t nearly as popular in the South as exaggerated, imagined mythologies would have us believe. Poplin (tan, taupe, olive) and worsted panama (especially “Cambridge Gray”) were key for summer. I don’t recall anybody wearing bright pink or lime green, but Charleston Red was an option for club dinners. Lilly Pulitzer was more Florida Palm Beach than Southern Ivy. The most flamboyant items in most Southern natural shoulder wardrobes were glen checked tweed jackets, pale yellow oxfords, and tasseled mocs.
Your recollection and mine are almost identical. The more colorful items associated with prep were simply not part of collegiate/Ivy dressing. I did not see patchwork Madras until the 1970s. The Madras jackets you saw at school in late spring and early fall were in a palette not that different than the tweeds. I remember pale blue pin-cord in Virginia summers but not much seersucker. The first deviation from subtlety that I recall was when larger paisleys arrived around the time of Carnaby Street. Shirt colors now widely accepted such as light green and lavender were non-existent. Pink was present in Virginia but unusual.
Samuel, I agree with you wholeheartedly about the importance of understatement. I do believe that it is the pinnacle of Ivy Style. Once we veer off into being ostentatious, we have lost the basic ethos of the style.
You did a good job. I agree with you about Southport.
Thanks so much. Here is an excellent article about Southport by my friend Jessica Gordon Ryan:
https://newengland.com/travel/connecticut/southport-connecticut/
I forgot to say you represented the Ivy Style brand well. In other words, you made us look better than we are.
Thank you, thank is too kind.
S I You talked about poplin suits in your comments I can remember in 1961 while I was in boarding in MA my parents taking me to see Charlie at the Andover shop in Cambridge and buying me a tan poplin suit . I think it was either a Haspel or Deansgate and a gant shirt for $75.00. The great thing about the tan poplin suit was that you could wear it as a suit or just the jacket with a pr. of summer gray flannels or just wear the tan pants.
A lot has happened since the original OPH was published. The Reagan era, accompanied by the 80s “Greed is good” mentality, and the Bush-Clinton-Bush era, when/where Yuppieism and Boboism (see David Brooks book) flourished. The Old Guard Liberal Establishment, including moderate and progressive Republicans, breathed their last breath (see Chris Hedges book), and the gap between middle-class Americans and the rich widened drastically. Even more comic/tragic is the gap between the rich and the super rich. This constitutes a problem for anyone who favors the sartorial excesses of “Preppy.”
There are reasons to guess old-fashioned Heyday era Ivy, subtle and understated (if slightly staid), will thrive as a form of vintage Americana. Cause for celebration. But “Preppy” will continue to decline. I can’t imagine a scenario where the sartorial totems of upper-class leisure are welcomed and embraced by a majority. Stated more bluntly: in thirty years there will be no market for patch madras or embroidered whales, lobsters, and tennis racquets, and retailers who’ve peddled pink-dyed canvas clothing will wring their hands anxiously.
The style many of us appreciate, an American take on certain British goods, wasn’t born in New York or an entrepreneurial New Haven tailor’s office. The market for the flannel, challis, oxford, and tweed preceded the marketing, which means an already existing culture inspired its introduction to an American audience. That culture, the Liberal/Mainline Protestant Establishment, has been dying slowly yet surely since the 70s. Deemed quaint and useless (Cy Vance and Sarge Reynolds were paragons) by the more radical elements of American society, the fade has been steadfastly constant.
There are still a few remaining corners and crevices, but they’re few in number and hidden (hiding out, actually) and languishing. J. Press was saved by a Japanese retail giant (a hobby for a few Japanese “trads”) and honesty demands that O’Connell’s, the only remaining Ivy outpost, will not expand operations anytime soon. A safe guess is both have persevered only because of the online sales.
Business school 101: A culture creates a market. When the culture dissipates and dies, the market, gasping for air, follows the slumber to the grave. Digby Baltzell predicted hopefully that American patricians would teach the rest of us how to invite and practice their long-held values, including discretion, generosity of spirit, noblesse oblige, proper manners, and kindness.
I admire his optimism, but he was wrong. America is not the “kinder, gentler nation” with which the Old Guard Liberal Protestant Establishment was entrusted. Their stewardship, honorable and noble, was overwhelmed and vanquished by instincts and values that will fail us. The brash, hyper macho aesthetic, whether dressed up or t-shirted and denim’s, is as descriptive of the American soul — and prescriptive for anxious, fearful people who feel lost.
Samuel, thank for your eloquent and well stated commentary. I appreciate the reference to E. Digby Balzell, a true gentleman scholar. Baltzell inspired my career in academia, and references to his work feature prominently in my doctoral dissertation. Here is a quick story you might appreciate. A year or so after I graduated from Trinity College, I decided to reach out to Baltzell via a phone call. I used a certain black and orange social directory to obtain his phone number. This of course was the pre-Internet era of land lines. Baltzell was a bit gruff at first, not pleased that some stranger had contacted him while he was watching a Philadelphia Eagles game. I explained that I admired his work and he was profoundly influential for me. That seemed to soften him a bit and we proceeded to discuss a variety of matters. I told him that I had just recently graduated from Trinity College, but had applied to the University of Pennsylvania as a transfer student and almost went, but decided to stay at the small liberal arts college for fear I might get lost at the larger university. “Trinity is a good school,” he said, “I know several graduates.” But then he added, “Penn is better. You should have gone there.” I felt at that moment he may have been right. Penn is excellent, and I could have taken classes with Baltzell, which would have been the opportunity of a lifetime. However, I must say, I am glad I stayed at Trinity. Ironically, my experience at Trinity was the starting point for my path to running Ivy Style as well as my interest in collegiate architecture. Nonetheless, I am glad that I connected with Baltzell that one memorable time. May he rest in peace.
Off topic, I guess, but I need to know. There is a noticeable lump in your right hand shoulder. I have one just like it on one shoulder on one of my mtm, H. Freeman sack suits, which I complained about, here, last week.
Crux: Why on earth do manufacturers insist on doing this? It seems so unnecessary. I’m not in the business, so I don’t understand. Wouldn’t the logical default position be to just leave that out? Then, if the customer really wants a lump in one shoulder, wouldn’t he ask for it?
How about that — you spoke with Baltzell. Lucky you. I would have lacked the courage to pick up the phone and dial.
Your decision to avoid undergraduate life in Philadelphia and remain at Trinity was very wise. I’ll leave it there, but, when it comes to temperament/persona of alums, Trin trounces Penn.