Eternal Shoeshine Of The Spotless Kind

During the Covid-19 lockdown, the question arises for each of us: To dress properly, or not? To maintain one’s appearance, and deportment, and flair, or not? To continue to do what one does, what ones believe to be correct, even if no one else is looking? We all know the correct answer. Standards are to be maintained

American Legacy: A Q&A With Arnold Steiner

Arnold Steiner isn’t your typical fashion designer. He isn’t sickly thin, he doesn’t dress in black, and he rarely has a dour expression on his face. In fact he seems downright jolly, like that encouraging high school teacher that we all wish we had. Or like a dad who enjoys fatherhood because he finally gets

Dressing As A Rhetorical Statement

If the Northeast is the pinnacle of old money, Ivy Leaguers, and powerful men of distinction, then Washington DC is a close second. Though our democracy could use a few more of distinction in that city it seems. The men are bred and trained in the New English tradition and migrate down to the swamp

Courtly Attire: Associate Justice Stephen Breyer

The Supreme Court has been rebuked by figures on both sides of the political spectrum as being too partisan. For all of scolding it has received, however, one justice deserves praise for having stood alone in preserving not only the law, but trad style. Justice Stephen Breyer, appointed to the court in 1994, has unknowingly

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

The Chase And The Catch

Some people are lucky enough to be in the right place at the right time. Others have a hand in making that time and place the right ones. Chase Winfrey (Instagram: @chasehwinner) falls into the latter category. At only 25 years old, the Ohioan-turned-New Yorker is proving why he is one of the leading young

Wild About Cary

Cary Grant was the number-one trending topic today on Twitter, which is pretty unusual given what usually trends on Twitter. Granted —pun intended — it’s his birthday, but still it’s reassuring to know he’s so fondly remembered, and for good reason. Here are some images of him wearing a buttondown collar in a variety of

The Maestro Of Andoverian Garb: Boston Globe Tribute To Charlie Davidson

When a celebrated person dies and a newspaper does a full-length feature, I’m not sure if it’s technically an obituary. So we’ll call The Boston Globe’s piece on Andover Shop founder Charlie Davidson a tribute. Here’s some background on the man that few of us knew: Born in Lawrence in 1926, Mr. Davidson was of

Good Night, Sweet Prince: Exclusive Bruce Boyer Tribute To Charlie Davidson

There are men all over the place reminiscing and telling stories about Charlie Davidson. Everyone either knew him or knew of him. Charlie ran The Andover Shop in Cambridge for more than a half century, and saw to the sartorial needs of professors and politicians, students, jazz musicians, and mere male mortals who wanted to

Charlie Davidson, 1926-2019

A person close to Andover Shop founder Charlie Davidson has informed me that he passed away this morning. On a very personal note, I am also heartbroken to learn that he was recently told that I was moving Newport, where he has spent much of his life, and that he said he hoped to see

Imagine A World Without Ralph: Alan Flusser Discusses New RL Bio

Alan Flusser recently gave a talk about his new Ralph Lauren bio at the National Arts Club in New York as part of its FashionSpeak Fridays lecture series. Beforehand, I spoke with Flusser about the book, which was 12 years in the making. Photos below are by Jane Kratochvil and courtesy of National Arts Club.

Immortal Sole: Adlai Stevenson and the Boston Cracked Shoe

If you don’t live on the East Coast and are under the age of 60, the term “Boston Cracked Shoe” will not likely have any resonance. But being 77, and having spent all of my business career in the East, it’s a part of the history of the Ivy League Look that is impossible to

Well Aged: A Portrait Of Thomas Davis

A few days ago I met Tom Davis in Central Park to snap a few photos. I’m planning to share some of his spiritual wisdom at Trad Man (please chip in if you can; the Kickstarter campaign ends in a week and we’ve a ways to go), and needed a shot of him. We did

We Got Roger Stone: An Ivy Style Exclusive Interview

Update: As requested in light of today’s news, we revisit our interview with Roger Stone for you to bemoan or celebrate the verdict on his trial. After the publication of Friday’s story on political supervillain Roger Stone, contributing writer Eric Twardzik received an unexpected call from Stone, leading to an exclusive interview in which the

Slightly Out Of Toon

Most parents dream of their son getting accepted into an Ivy League school. On the other hand, the number of parents who hope their pride and joy goes on to become a cartoonist is probably close to zero. Whitney Darrow, Jr., the cartoonist we featured in yesterday’s post, had the ideal sensibilities to be a

Biden It Now

Another 180-minute Democratic debate has passed with few fireworks aside from ex-HUD secretary Julián Castro accusing Joe Biden of forgetfulness. Castro’s arrow may have missed its mark, but newly uncovered evidence suggests that the former vice president once left a glen check Ralph Lauren sportcoat at a Delaware dry cleaner, and it can now be

Preppy Hippie From Mississippi: An Interview With Sid Mashburn

Earlier this year I had a buttondown shirt made for me at a Sid Mashburn trunk show in Boston. Pleased with its quality, I reached out to the Mashburn team for details about their shirt offerings, both MTO and ready-to-wear. I received the answers I was looking for (it’s an unfused collar with 3¼” points), but

Preppy Evangelist: The Lisa Birnbach Interview

Given all the preppy ’80s talk lately, we revisit this 2010 interview with Lisa Birnbach, which was done about six months before the release of True Prep. The interview was subsequently used as part of the book’s press kit. — CC * * * IS: How did the new book come about? LB: It came