King Tut’s Tomb of the Preppy Era

Nine years ago this month, I wrote a story for The Rake on The Cary Collection. Inspired by a post by Unabashedly Prep’s Fred Castleberry (who supplied the photos), I made an appointment with Thomas Cary and proceeded to crawl through what he calls “the King Tut’s tomb of the preppy era,” trying not to knock anything



Smiling Through The ’80s

You’ve no doubt noticed in our recent coverage of the brewing Ivy trend that the mood of the photo shoots is rather glum. You can hardly blame them. It’s 2020, after all. I mean, I don’t smile very much either, and when I do, well let’s just say it’s not from joy but rather absurdity.



Ralph Lauren 3-Piece Sack Suit + Pinned Club Collar

We close out February with this fine example of what Ralph Lauren was doing back in 2011. The collection’s press release included the following copy: Polo Ralph Lauren presents a world of vintage preppy dressing inspired by the iconic Northeast, from a rugged Maine expedition to an urban Ivy League campus to charming New England


Spring Squeeze: Exclusive J. Press Brochure Preview

You’ve probably noticed over the past couple of years that J. Press has greatly improved its bi-annual brochures under the tutelage of executive Robert “Squeeze” Squillaro (I gave him that nickname, by the way, and he’s yet to tell me not to use it). The new one for spring-summer has just been posted online, and


Old Is New Again: An Interview With Old Money Style Author Byron Tully

  Old Money Style is latest in Byron Tully’s thoughtful series of books on the habits and practices those who have known the best in clothing, manner, and deportment for generations. He puts these ideas into practice, and across the series, emphasizes that old money is about much more than the money itself – and


The Hue Is Olive Gray

Frequent comment-leaver SE sent in this vintage Southwick ad promoting the color “olive gray.” Alas as the image is in black and white, we can only see the gray. Enjoy the rest of your Sunday evening, and see you tomorrow with a stimulating Q&A on the charm — and status — of old clothes. —


Green Is Good: Norman Hilton Lovat Windowpane Sportcoat

Our series of posts on the color olive comes to an end with a peek inside the armoire at Ivy-Style.com headquarters back in 2011. This is one of the Norman Hilton sportcoats that his son Nick relaunched at the time. I picked it up at the New York factory where it was made; Nick Hilton gave


Take Olive: Drab Dress on the College Campus

As “Take Ivy” becomes a menswear touchstone once again, we revisit this post from the last time around, in which I wrote that the lasting legacy of the book will be isolating certain motifs. It’s like rewatching a movie: First you take in the whole, and then in subsequent viewings you focus on more subtle



Black History Month: The Guys Of Ivy’s Facebook Group

Five years ago I asked the members of Ivy’s Facebook group if they’d like to have their uploads shared here. They agreed, and as February zooms by, I’d like to share this post once again. I’ve always particularly like the above photo. As I wrote back in 2015, you’ll notice that when it comes to dressing


Color of Conquest: Bruce Boyer’s Ode to Olive

Olive and khaki were enormously popular colors for Ivy-styled civilian clothing directly after WW II, through the Korean Conflict (fighting ended in 1953), and a decade beyond. We can only surmise that the wealth of well made but inexpensive military clothing on sale in Army & Navy stores throughout the country after 1945, as well


Ivy Trendwatch 2.0: The Most Compelling Reimagining Ever

Over the past year or so there have been murmurings — that is, media coverage — of a nascent Ivy League Look trend resurgence, thanks in large part to Rowing Blazers. Now GQ UK has a new article entitled “How Ivy League style came back into the fold.” And to think, it was just half a


Confessions of a Preppy Snob

Slate Magazine recently posted a long-winded and at times insufferable meditation on snobbery by a prep who came of age in the ’80s. The author’s resumé would certainly suggest the presence of snobbery: Mark Oppenheimer writes about religion for the New York Times. He is the author of a memoir, Wisenheimer; is an editor of


Valentine’s Day Special: Ken & Barbie, The Ivy Years

For devotees of The Ivy League Look who live in 2017 but who aspire to buy clothes in 1957, there are two pieces of technology that can help. While the best option is a time machine, it is unfortunate that they are still notoriously unreliable, as any number of movies illustrate. The second option is


It’s Still Shaggy Season

Someone over at InsideHook (formerly Real Clear Media, for which I wrote a few pieces) is an Ivy stylist. The site just put up an ode to J. Press’ classic Shaggy Dog sweater, which comes in an extra-high number of flavors this year. Writes Jason Diamond: The Shaggy Dog, for those that don’t know, is


Lightness in the Loafers

There’s something about light-colored socks that puts a spring in your step. As you move, you catch the light color from the corner of your eye, especially if you’re wearing pants with a barely-there break. Gradually this sinks into your mind so that you’re always slightly conscious — which is not the same as being self-conscious


White Socks: Not Just For Old Men

Reposting this in light of a comment on our previous post “The Chase And The Catch,” regarding white socks being dorky. No personal opinion on the matter, as I believe it depends primarily on whether or not the wearer is a dork.  — CC