Behold The Rules Of Ivy

Threading the Needle ~ Behold The Rules Of Ivy 

Over a decade has passed since I transcribed “The Rules Of Ivy” while asserting my role as co-curator for the Ivy Style Exhibit at The Fashion Institute of Technology Museum, experienced by over 50,000 onsite spectators.

Setting forth the Rules of Ivy, G. Bruce Boyer, my ongoing Fashion History Mentor (English Literature Professor former Fashion Editor at Town and Country, Esquire, GQ) penned the Foreword to my book Threading The Needle. “In 2011, Patricia Mears, deputy director of the Museum at FIT, asked Richard Press and me to assist her in curating an exhibit on Ivy Style,” he recalled, “we both jumped at it.”

In a squib from my recently released book Threading The Needle II, Patricia updates her enthusiasm of the memorable event, “How lucky was I to have Richard, along with G. Bruce Boyer, be my Ivy Style partner and guide?” 

An enclosed note from a time past recalls my forbearance for rules of the game. Four balls a walk, three strikes you’re out. Here’s a further take from  chapter 42 in my new book titled The Lucky Seven Ivy Essentials reworked for the current column: 

GREY SUIT:  If you don’t regularly wear a suit, make it grey. Blue is too formal for daytime wear. Keep it geared up for board meetings, funerals, if you get elected to Congress or appear in court as defendant or counsel. 

BLUE BLAZER: Sorry, the old standby. Fake suit with Grey Dress Trousers or Country Club Chic with Tartans, Khakis, White Ducks or for JG Melon’s ragged bone Jeans.

OXFORD-CLOTH BUTTON DOWN: Historical precedent—President Jack Kennedy at Hyannis Port in rolled up OCBD quarterbacking touch football with Brothers Bobby, Teddy similarly attired.

Include: loafers, dirty white bucks, khaki trousers, repp ties, Oxford cloth boxer shorts, Camel Hair Polo Coat, Shaggy Dog Shetland sweaters, Harris Tweed Sport Coat— the whole shebang undying good taste from Yesterday for Today and Tomorrow. 

Seize the moment to get the full take of THREADING THE NEEDLE II @jpressonline 




The key to understanding the “Ivy look” curated by J Press is the quality and durability of the materials and skilled craftsmanship offered. Such clothes are “wearable art” and connect us to the past but also to contemporary needs for natural fabrics that are long-lasting. Re-crafting shoes and mending wool and cotton garments is in tune with the times. Permanent style rather than disposable fashion is ecologically sound. When jeans are sold new with tipped knees one wonders how unbalanced things have become. J Press thrives because enough people care about quality. Simple as that. Thank you.

Robert Lee Kilpatrick March 02, 2023

Well, I never went to an actual Ivy League school, but I did go to UVA in the late 70s. I basically still have this as my go to look whenever I have to get even moderately dressed up. I was one of those who continue to wear the blue Oxford shirt, navy blazer, and khakis, typically along with brown dress shoes, long after my firm went to “business casual“ 24×7×365. I worked in Manhattan for most of my adult years, but retired and moved to Minnesota. There are no “opportunities“ to do anything, but be casual here, so I have to manufacture them. What’s bred in the bone…. Cheers

Tom Minet January 09, 2023

Sound advice as always.

Sadly my tweed is not the “real deal” (i.e. Harris) but my Magee Donegal sport coat and Fox birdseye flannel trousers are making up for it! Happy X-Mas!

DCLawyer68 December 01, 2022

If anyone thinks gray trousers don’t look right with a navy blazer, it’s because they’re cheap.

No one’s ever confused someone in a J. Press blazer and gray flannels with a mall cop…

And for those who aren’t color blind, brown shoes are wonderful.

DCLawyer68 December 01, 2022

Very sound sartorial advice, as always, Mr. Press,
You are our Virgil.
But may I offer one very small edit?
Avoid the navy blazer with gray trousers-appears to have become a bit of a cliché, too much like a museum attendant or security guard at the Oscar’s.
Instead, also invest in a navy suit (A wonderful, sack style from J. Press, of course!). But for God’s sake don’t wear with brown shoes! If you do, at least have the common decency to do it secretly and never tell any one about it. I plead the fifth.

Don Quixote November 27, 2022

Among his other talents, frequent contributor Robert Emmaus never avoids an honest appraisal of his journey to appropriate Ivy League dress. Witness his recent admission.of lacking an OCBD for oran appearance at a1962 S. A. T. date. I shared his lack of appropriate basic attire back in 1947. Growing up in a tiny Massachusetts town, my family kept me dressed in the latest W W 2 inventory of the local military surplus store. Not a single Ivy item in sight.
Fortunately, a year later found me as a freshman joining one of the 37 fraternities at Penn. Heavily populated by aspiring undergrads at the Wharton School, I found myself surrounded by a sea of blazers, button downs, repp ties, khakis and greying (once white) bucks. With the help of my understanding family (and the funds from dishwashing in the fraternity kitchen), I slowly began to acquire that special comfort of dressing like almost everyone on campus. The beginnings of feeling at home to this day in my ever appropriate 3 button, soft roll, pleatless wardrobe.

Stan Pilshaw November 27, 2022

Yes, yes, yes!

Kind Regards,


Heinz-Ulrich von Boffke November 27, 2022

Outstanding information as always Thank You !

Michael Murphy November 27, 2022

My first encounter with the rules of ivy was the embarrassment I felt at the S.A.T. exam at Park School in Indianapolis in 1962 when I—-an accomplished public school scholar—was the only student wearing a white broadcloth dress shirt in a sea of blue OCBDs!

Robert W. Emmaus November 27, 2022

Leave a comment

All comments are moderated before being published