The Preppy Costume Days Are Over

We posted this back in 2012. Given recent speculations of COVID’s fatal blow to the way people dress (more on that soon), maybe a preppy costume revival isn’t such a bad thing. * * * A few weeks ago Esquire’s Matt Sullivan wrote a piece about his high school reunion. And not just any high


Relaxed Elegance: Drake’s Collection Three, 2020

Drake’s, the classic English menswear brand, pens itself as being under the guiding philosophy of “relaxed elegance”. Originally opening in 1977 in East London, Drake’s is still to this day arguably best known for its neckwear, and despite a clear Italian influence when it comes to their tailoring, houses an array of pieces that would


Ivy Trendwatch: All Roads Lead To Ivy

… and those that don’t, lead to prep. So relax: There’s hope for the future. It’s just that the future includes critter pants. This chart from that other world known as 2012 brought out some lively discussion. Fashion cycles churn fast these days, so you never know….


The Dye Is Cast

Does anyone remember the movie where a character says to another, “We seem to have passed that point where life stops giving and starts taking away.” In what in the big picture is a necessary cosmic correction for our consumer-based society, two more major retailers with trad connections have filed for bankruptcy. Both of them


A Highly Refined Sense Of Style: Esquire On Buttondowns, 1983

George Frazier snagged a mention here recently, which makes this post a nice follow-up. It’s one of many things that’s been sitting in my inbox for quite some time, sent by a colleague. It appeared in a 1983 issue of Esquire and is being posted here for the first time. Head over here to sign


Holly And The Ivy: Retro Rocker Nick Waterhouse

If you haven’t heard of this great musician with great style, here’s a reminder to give him a listen. * * * The June issue of GQ, while also including Justin Bieber, devotes a full-page profile to Nick Waterhouse, a Southern California singer and guitarist who takes his music clues from Buddy Holly and songwriters


Golden Years: A Tummler On York Street

A New York Times obit for a recently deceased Borscht Belt social director described his job title, “tummler,” a Yiddish word for someone who stirs up tumult or excitement, a jack of all trades. J. Press salesman George Feen (above left), known around New Haven as “Little Georgie Feen”, was a tummler on York Street


The Decline Of Prep?

Back in 2013 I wrote a 9,000-word essay on the Ivy League Look which I’m honored to say Alan Flusser considers “definitive.” As far as meta-analysis goes, I haven’t had much to say since then. However, perhaps the time will soon come for an addendum. In “The Rise And Fall Of The Ivy League Look,”


Poised Or Oblivious? The True Essence Of Prep

Back in 2012 columnist Mark Oppenheimer penned an essay about prepdom for Salon that’s pegged on Whit Stillman’s new movie “Damsels In Distress.” The piece is more thoughtful than the usual stuff that gets said about the cultural phenomenon known as preppy. Oppenheimer’s thesis is that preppy is more than a style of dress. This


Monday Grab Bag

Today we feature a random assortment of vintage images that have been lying around in an old shoe box, metaphorically speaking. And yes that’s a pun on “shoe;” after all, some of these images are from Yale.   This one, however, is from an altogether different kind of campus shop:   College men were once


The Cleanest Cut: Remembering Dick Clark

A clean-cut appearance has always been part of the Ivy League Look. With a soft-shouldered jacket and Princeton haircut, a young man could conveniently mask his salacious intentions. After all, what father could fear for his teenage daughter’s honor while on a date with a boy wearing a cardigan? In the 1950s, this kind of


Hot Or Not? George Frazier, Charlie Davidson & The Duende Game

Recently I had drinks with members of Charlie Davidson’s family, and the subject of George Frazier and the duende game came up, which made said family member shake their head, as if it had come up one too many times at the dinner table. For those who don’t know what “duende” is, proceed to become


News Roundup: Brooks Bid, Gitman Shirts, Loafers And Lockdown

Remember how in the ’80s Brooks Brothers was bought by a department store company, beginning its decades of downfall? Well the new owners could be even more odious: a shopping mall company. Reported yesterday and updated this morning, CNBC writes: A company known as Sparc LLC, which is comprised of the U.S. mall owner Simon


The Ivy League Look In Australia In The ’50s

During the heyday of the Ivy League Look, the natural-shoulder diaspora spread not only from the Ancient Eight to campuses across America, it also spread to far corners of the globe. In March of 1957, The Sydney Morning Herald reported on the growing trend for American Ivy League clothes. Farmer’s is a department store that


Chasing The Ivy Image: USA Today Op-Ed On Brooks In The ’60s

Today’s edition of USA Today carries an interesting op-ed from an African American who worked at Brooks Brothers in the 1960s. The piece is entitled “As a young Black man I grew up chasing Brooks Brothers’ Ivy image — then I grew out of it.” Robert Hill writes: Brooks Brothers largely created the Ivy League look,


Mitchy Matchy

The past few summers I’ve gone into Nature Man mode. I think there’s a post called “hippie Ivy,” and I’ll probably do a surfer hippie Ivy post in September at the end of my first summer in Newport. But previously I was able to balance the barefoot, shirtless wanderings through Central Park with a jacket


Spring Fling: 1960s Bermuda College Week Footage

Looking to regain a foothold in the Spring Break market, The Bermuda Department of Tourism dedicated themselves last year to relaunching College Week in the form of Bermuda Spring Break 2012. Taking a page from the old College Week, students were given a pass for all sponsored events, complimentary food, free public transportation and discounted


Dirty White Bucks & An Ivy League Coat

We’ve previously featured pop tunes from the Ivy heyday (and from the good old days when guys would sing about their clothes), and here’s another one: Ronnie Haig & Jerry Siefert singing the praises of dirty white bucks and “an Ivy League coat to burn out your eye.” Ignore the references to tight pants. 


Brooks Brothers Obituaries

The past week has seen a slew of features in major publications on the announcement that Brooks Brothers is bankrupt. Many see it as the end of this hallowed American institution and symbolic of a certain period in American life that has reached its end. Here’s a roundup along with some choice passages. Forbes: Brooks Brothers