Sack Suit Perfection: An Interview With Japan’s Boston Tailor

On one of my many trips to the mid-century American oasis amid the typical British High Streets, that special place called John Simons, I found a really neat navy blazer that had all the right details: 3/2 button stance, undarted sack fit, patch pockets, two-button cuff, stitched edges, hook vent, and of course, natural shoulders.




When LIFE Gives You Lemmons

Here are a few shots of actor Jack Lemmon from the LIFE archives. Lemmon played many sack-suited characters throughout the Ivy heyday. He’s pictured on the set of “The Apartment” in 1959 in a classic outfit formula you should try if you haven’t. You take a simple solid suit and tie (often a knit), and for subtle


The Man In My Grey Flannel Suit

When I was a young fogey in my mid-twenties, I had a number of vests so that I could sport a pocket watch and chain. It was an absolutely fobulous time in my life. Recently I got the urge to break out the watch once again, but this time I wanted not just an odd waistcoat,


Tea and Sympathy, 1956

“Tea and Sympathy” is one of the books on the reading list featured in “The Official Preppy Handbook.” Written by Robert Anderson for the stage, it was adapted for the screen in 1956 with Vincente Minnelli at the helm. “Tea and Sympathy” is set at a boys’ prep school, where sensitive Tom Lee (played by John Kerr)


A Day In The Life Of A Fool

In the midst of the heyday of the Ivy League Look came the short-lived music trend known as bossa nova. It hailed from Brazil and was soon picked up by many American musicians, even Frank Sinatra. One of the genre’s biggest hits was “A Day In The Life Of A Fool,” by composer Luis Bonfa,


Brothers In Arms

Last night The Armoury in NYC held an event for “Ametora” author W. David Marx, who lectured on Ivy, trad, prep and workwear in Japanese magazines. Like his similar lecture several months ago, it was very well attended. This time, however, Marx brought a generous sampling of said magazines, some of which go back to the ’60s.


Pipes and Cardigans Get the Chicks

Playboy in its early years was certainly an innovative magazine. In contrast, or rather complement, to the buxom beauties, the magazine’s inclusion of jazz and literature, plus references to Nietzsche and psychoanalysis, gave it a highbrow edge not found in today’s magazines, in which articles on socially relevant topics, rather than aesthetic matters, provide the weight. Moreover,


Reflections Of A Relic: Wearing Suits And The Rhythm Of Life

Corporate culture continues to change or evolve, and the suit now seems to be headed in the same direction of the buggy whip. Not long ago, however, there were practical and professional reasons to wear a suit and tie while doing business. First and foremost, the suit was a way of demonstrating respect for those you


Lost City: John Lindsay’s New York

John Lindsay, mayor of New York from 1966 to 1973, personified the resolute confusion with which clubby, liberal WASPs faced the social upheaval of the era. Entering politics as a successful young lawyer, Lindsay represented the wealthy Upper East Side of Manhattan, known as the Silk Stocking District, in Congress from 1958 to 1965. While serving,


Pleasant Encounter: The Tom Davis Interview

Note: Post updated; scroll down to section marked Part Two.  When I first arrived in New York, I was told about an old guard legend named Tom Davis, who had been running the custom shirt program at Brooks Brothers for going on half a century. That’s interesting enough, but Davis’ story has a fascinating twist: he


Happy Feet

This image from the Japanese illustrator Hiroshi Watatani brings several things to mind. First there’s a formula you rarely see, and that’s a completely sober outfit — like this one in black, white and gray — combined with colorful socks. I’ll do a slight variation, wearing a solid tie plus rep-striped or motif socks, essentially transferring the patterns from


Natural Style: Dartmouth in the ’40s & ’50s

A tour of Dartmouth College’s library in the 1950s, shown in the top video, sheds light on the school’s lifestyle and sartorial history. Male students seen hard at work wearing sweaters, flannels and thick trousers highlight two things: The lack of female students and a clear fashion sense unique to the college. Dartmouth did not


J. Press, A Frat House Where Everyone’s Dad Is Rich

I recently discovered this article about J. Press buried in the files on my computer. Richard Press sent it to me so long ago he doesn’t even remember it. He says he believes it’s from 1987 and a magazine called Success. Consider it successfully resurrected. — CC


Island Awakening

  In the summer of 1979 I traveled from my home in Louisiana to visit a girlfriend who was summering in Nantucket. She was working as someone’s nanny and sharing a home with about 20 similarly employed youths. The girlfriend thing turned out to be a disappointment, but Nantucket was something to remember. I had


My Kinda Clothes: Shoes To Persevere Through Troubled Times

I really should be writing my dissertation now, but a combination of pristine Spring weather, study fatigue and an unashamed adoration for Clarks Wallabees has compelled me to write about “my kinda clothes” instead.  Ever since Ivy Style threw these contrarian shoes in front of my headlights, I’ve been infatuated with their horrific silhouette. Wallabees


Deer, Have You Seen My Loafers?

Recently an interesting pair of loafers came on my radar. They’re made by TB Phelps of deer hide. I reached out to the company to find out more, and here’s what they said. The loafer model is called the Ventura and comes in chestnut, black and tan in sizes 8-13 including half sizes. It also


Harvard Commencement, 1961

Shot for Life Magazine by Alfred Eisenstaedt, the same photographer who brought us the wonderfully atmospheric shots of New Haven commuters. Top hats and morning coats by day, white dinner jackets at night.