It Was A Very Good Year

Frank Sinatra sported J. Press Ivy in 1969. It was a very good year.
Sinatra’s gone, but J. Press Ivy is still here and thriving.

Sinatra found himself drawn to the staples in the J. Press product line—especially blue blazers. By my estimate he must have ordered about a dozen of them from us—four or five with his first order of suits, and one or two each time he would come to the store to order new clothes. Explaining that the blazers also needed to be appropriate for the climate of southern California, he was especially partial to the easy drape of our doeskin flannel (a mid-weight 11-12 oz.), as well as to the pure cashmere model that iconic fitter Felix Samelson reworked with hand-sewn edges, and several more durable worsted jackets “for the plane.”

It helped to keep things running smoothly on the business end with J. Press that Sinatra’s tastes in suits and jackets were refined, his knowledge of fabrics extensive, and his marching orders to us succinct. I took notes, both in real-time for Felix and as it turns out, for posterity: “Three on two-button stance for all the jackets. If I unbutton the coat I want the collar roll to the lapel from the middle button. I never button the top one. I always show 3/8 inch of the shirt sleeve. Cuff the pants clean to the tip of my shoes and take out all suspender buttons. I’m a belt guy.”

Felix always maintained that compared to the intricate and exacting demands of our hairsplitting, over-officious bespoke customers, Sinatra’s instructions were straight ahead, easy to follow, and consistent with someone who had undergone extensive fittings for suits and accessories over the course of thirty-year professional career. It helped the master tailor to relax considerably when as a new customer Sinatra barked “Stash the chalk—it’s perfect” after returning and deciding he needed to try on only the first of the half-dozen suits Felix had altered for him. As he buttoned the Herringbone Tweed Suit he said to me, “Hey, Richie, do I look like I went to Yale?”

During a solo visit to J. Press, a short time after his initial suit-fitting, Sinatra shouted over to me, “Now what else do you have in this joint to show me?”

I led Sinatra on a tour of the store and he eagerly picked out sport coats, ties, Oxford button-down shirts, Shaggy Dog sweaters, argyle socks and anything we had in orange—pocket squares, sweaters, and sweater vests. One of his pals explained that Sinatra had a special love of all things orange, a color he considered to be “upbeat.” His California home was said to be decorated in an array of orange hues.

“Put together what goes with ’em. Same stuff you sell to your Yale big shots.”

Even with Sinatra it always comes back to J. Press and Yale. Over a few Jack Daniels he once mocked me, “Hey Richie, how the hell did you find any broads in the woods up at Dartmouth?”

“Frank,” I told him, “I Did It My Way.”



Great article Richard!
I have been shopping at J PRESS for 50 years.
I saw Sinatra live 4 times and had a small 8 piece orchestra for about and we did all of Sinatra’s music. Anyhow, thanks for the nice article.

Mark Mack January 20, 2020

These steps great stories of the style that makes J.Press a unique store.
I wish I had exact precision demands on my clothing!
But everyone in the NYC store thankfully helps me completely!

Patrick Simmons Harrigan January 15, 2020

I remember a Sinatra sighting in the late ’60s in a stairwell at Yale-New Haven Hospital (a photo from the New Haven Register at the time will confirm this) where Sinatra was clearly annoyed to have been sighted.

Robert W. Emmaus January 14, 2020

The lower center picture shows Sinatra in what appears to be a V-neck shaggy dog. I have not seen these for a long time and would love to see them offered again. Crew necks are classic, but those of us with short necks would enjoy wearing a shallow V-neck version to avoid the sweater snagging on our necks and faces :-). Thanks for the great article.

E. Nimmer January 14, 2020

Richard— I love reading your column and eagerly await my emails. Classic one about Sinatra. My Grandpa was a big fan of J. Press, and so it carried over to my Dad, and then me. Your suits were all I ever wore, when I lived in Boston. I felt like Dennis, your salesman in Cambridge, was like family! Thank you for continuing on with the 3 button tradition!

Jim Lion, Jr. January 14, 2020

Another classic story, Richard! Thanks.

Charlie Hotchkiss January 13, 2020

Fantastic story
He always dressed well. Didn’t think he was an Ivy League style man. But he looked great in those photos

Howard Goldstein January 13, 2020

I was fortunate to see Sinatra in concert along with Sammy and Liza in 1989. There has never been, nor will there ever be, anyone like him.

Graham Kimbrough January 13, 2020

Your informative Newsletters are much enjoyed. I always wore Drumohr sweaters when I was on the other side of the Green Mountains at Middlebury, and I now own almost every Shaggy Dog color…but I miss the cable knits. And, as I wrote once before, I urge you to enlarge your offering of 3-button tweeds and suits.

Dave Tura January 13, 2020

Another good read for us old enough to have experienced the 1960s.

Thanks -

Mason Burnette January 13, 2020

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