Paul Winston’s bold suit linings are so famous, many clients select the fabric for the lining before the fabric for the suit itself.

Vivid linings are just one of the signature styles of Winston, the renowned tailor who began working for his father Sidney’s New York-based clothing company Chipp in 1961. Chipp soon became renowned for inventing the patching of madras and tweed, and for dressing President Kennedy.

Winston stayed with Chipp until the company’s dissolution in the early ’80s, and currently operates Chipp2/Winston Tailors out of a fifth-floor office in Midtown Manhattan.

Sidney Winston founded Chipp in 1947 following many years with J. Press, where he began working after high school. Previously located near 44th and Madison — among the cluster of traditional clothiers Brooks Brothers, J. Press and Paul Stuart — Chipp at its peak employed 30 tailors and a sales force of 10, and offered both custom and ready-to-wear clothing.

Paul Winston, now 70, attended Hopkins Grammar School, a small prep school in New Haven that is one of the nation’s oldest. He went on to study at Union College in Schenectady, New York. After joining Chipp, he commuted by train from Stamford for 37 years.

Winston currently resides in Wayne, NJ, where he boards a bus every morning at 6 to get to the office around 7. As further evidence of his dedication to the art of tailoring, he often works at home until midnight. “I figure the older I get the less time I have,” he says, “so I ought to be doing something other than sleeping.”

Winston recently spoke with Ivy-Style founder Christian Chensvold about Chipp’s heyday, his current clientele, personal tastes, and his dislike of any kind of dressing orthodoxy.

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IS: When your father left J. Press to start Chipp, what was his vision for the company?

PW: It’s just the American Dream to want to have your own thing rather than work for somebody else. My father was a natural salesman. His first job at J. Press was going to all the prep schools. He was just a kid out of high school himself, and he met a lot of people who became really important, but he met them when they were contemporaries of his, and there’s a big difference in the relationship you have with someone you meet when you’re both 18 years old. He met Thomas Watson Jr. of IBM and Cyrus Vance and that caliber, and had a relationship with them for the rest of his life that was much warmer than if he’d just met them later.

IS: When would this have been?

PW: He was born in 1912, so it would have been about 1930. At that time Brooks and Press traveled all over the country doing trunk shows. They also went to certain prep schools and colleges. My father knew a lot of people who went on to work in New York after they finished school. He started Chipp with a man named Lou Praeger, who also worked for Press as manager of the store in Princeton.

IS: When were the company’s golden years?

PW: I’d say the ’70s.

IS: The Ivy League Look went into fairly rapid decline sometime after 1965. What allowed you to thrive in the ’70s?

PW: We had a niche that continued, even though the Ivy League Look in general was declining and was probably bigger in Japan. But our customers wanted it, and many still want it today. Certain people object to calling it “Ivy League,” but however you want to call it, we still have that niche we’re filling with more completeness now than ever because there’s really nobody doing it anymore.

IS: Well, that’s not entirely true, because there are still clothiers who offer sack suits.

PW: Yes, but they’re not carrying them exclusively. Customers tell me all the time that the Press three-button jacket isn’t what it was. Yes, you can find an undarted jacket someplace: The difference is that they will have very lean pickings, while we have hundreds of swatches to make them from. No one can afford to carry a whole range of suits, so what they have are the very basic things.

IS: What do you call your style of clothing?

PW: Conservative, natural shoulder… a 3/2 jacket, slightly fitted, no pleats… Everyone had cuffs on the trousers and two buttons on the sleeves.

IS: But if today a stranger asks what style of clothes you make, what do you say?

PW: We make clothing for traditional, conservative businessmen. The edgy, way-out guy was never our customer. We had a few Hollywood types, like Andy Williams and Peter Lawford. Lawford was English, and he brought in John F. Kennedy when he was still in the Senate, and then along came the other Kennedy brothers and the Shrivers.

I didn’t arrive until 1961, and when it was really called “Ivy League” was before I got there. I never heard my father describe it that way. People who were in it resisted the term; it was more for people from the outside. Every Japanese customer who walked in always used it.

IS: Even at that time you had Japanese customers?

PW: We had some, and more as time went on. We made a bunch of stuff for a Japanese store just last year. They still think of “Ivy League” as something special, and they all know we made Kennedy’s clothing. A lot of them want to have their picture taken with me, and then every once in a while someone sends me a newspaper from over there with my picture and an article.

IS: Kennedy’s suits seem to have a bit more structure to the shoulder and some waist suppression.

PW: We always had some waist suppression, more than Brooks and Press. We were always slightly more updated than they were. No one is pure anymore, but Brooks was there first with readymade clothing. When readymade came into being, both Brooks and Press were very pure with three buttons and virtually no shaping. My father was greatly influenced by that because he worked for Press. We didn’t have darts, but we had a little more side suppression. But it was a very fine difference.

IS: Were you Kennedy’s exclusive clothier?

PW: As far as I know, though I can’t say that as an absolute fact.

IS: But when we see photos of him during his presidency, there’s a high likelihood he’s in Chipp?

PW: Yes, even the hat that he would carry and would never wear. My father went to the White House many times, and I was with him many times when we were fitting JFK at the Carlyle Hotel in New York. It was possible that he was buying from other people, but it strikes me as highly unlikely, given the amount of time he would have needed. His life wasn’t spent fitting clothing, and given that his brother and brother-in-law and everyone were all customers, and we sold them a lot of stuff, we had to have been his major supplier.

IS: Did Kennedy have particular tastes?

PW: He had things he liked. He was a very personable guy, and I was young at the time, and of course he had known my dad for 10 years. After he had bought stuff he always turned to me and said he wanted me to pick one out for him. But he always picked things out himself.

When we moved, I threw his pattern out. I picked it up, along with all the other patterns of customers who had died, and said to my brother, “Well, we don’t need this anymore.” And while we never did anything for Aristotle Onassis, Jacqueline would come in and buy him swim trunks and things like that. She would just walk in the door and people wouldn’t recognize her in her big sunglasses. But after her death, when they were auctioning stuff off, people were paying gigantic amounts of money for anything connected to him. And I’m sure that that if I had his pattern and some swatches of cloth I could have gotten a lot of money for them.

IS: So there’s nothing of Kennedy’s that remains?

PW: Only memories. We never took pictures with him, because my father thought that would have been a classless thing to do. But I have the memories and thrill of having done it, and at the age that I did it.

IS: You say you cater to the conservative businessman, and that you aren’t edgy or wild. But Chipp’s legacy seems to be its wild patterns for suit linings. And then there’s the patching of madras and tweed for which Chipp was known. So was Chipp the most experimental of the Ivy shops, or the most conservative?

PW: Well my father was the person who created patches originally— I know that. As for the linings, you can be very conservative in your dress and still have bright linings. And a lot of people who were conservative in their business dress, would be willing to do things that were very different in their sportswear and casual dress. Someone like Thomas Watson Jr., who wore a very conservative suit for business every day — we used to make really wild sports jackets for him.

IS: You’re talking about the WASP tradition of what is sometimes called the “Go-To-Hell” look — lime pants and madras sport coats. What’s your take on how that tradition came about?

PW: I have no idea how, but it certainly did come about. I would say that there were and still are people who are secure enough to do what they get a kick out of, without being concerned with what others think. I’ve always said that the common thread among all our customers through the years is that they are all very secure in what they want. When I joined in 1961, we had 30 colors of corduroy.

I don’t consider our wild linings and patching to be way out or edgy, because the people who were wearing them were conservatively dressed in conservative styles.  Watson, for example. Now IBM was famous for requiring white shirts if you worked there. Watson was very conservative in his dress, but had wild linings inside his suits. And if you ever saw him on vacation or in an informal setting, you’d see him wearing really bright, colorful things, but they weren’t bold in the model or style.

IS: What are Chipp2′s current rates for bespoke suits and jackets?

PW: Bespoke suits start at $2,500, and there aren’t many doing it close to that price. For made to measure, which we still cut ourselves, it’s a thousand dollars less. Also, I have some cloth that goes back to when my dad bought it. It’s good English cloth. When someone uses that, I price a suit the same as if they had brought the cloth in themselves, since we’ve had the cloth for so long and got it at such a good price.

Also, I find I’m uncomfortable when someone asks me to make something for them where I feel they have to pay me more than they should. Case in point, when people ask me to make poplin trousers. I say, “These are your clothing Miranda Rights: You shouldn’t be buying poplin trousers from me, because the cloth we’re using is a better make than the cloth deserves, but it still costs me the same to make trousers out of poplin as the world’s finest flannel.” As a result, while my price on the flannels is better than everyone else’s, my price on the poplin is more than you should be paying for poplin. I say that, and many tell me, “But I can’t find the colors I want, and I want a higher or shorter rise, and I can afford it.” So I do it and sleep well because I told them they shouldn’t be paying me for poplin or seersucker.

I think the majority of men don’t need custom clothing. Anyone can enjoy it, and it will feel different from off-the-rack. But we can fit 90 percent of people in made to measure, because we’re cutting it ourselves and creating an individual pattern.

IS:  Of your current customers, how many want an “Ivy League”-style suit: undarted jacket with 3/2 roll, and plain-front pants with cuffs?

PW: Our niche is that we offer that which you can’t find anywhere else, so certainly a measurable percentage of our customers are looking for that, but not the overall majority. The majority want a slightly more updated version. They want a dart because it gives more shape and looks more flattering. My guess would be 25 percent want the old classic. As for pleats, back in the heyday we never asked if a customer wanted pleats: No one got pleats.

IS: What about now?

PW: Now a measurable percentage of our customers wants pleats.

IS: If they’re getting some waist suppression and pleats, are they still getting a 3/2 roll and a two-button cuff?

PW: Yes.

IS: What about lapped seams and a hooked vent?

PW: They are in certain things — certainly in sports jackets they are. We never did lapped seams on gabardine, gray flannel, or chalk-striped suits.

IS: And even with darts on the jacket, clients will get a plain-front pant?

PW: Yes.

IS: Darts don’t require a pleated pant?

PW: Absolutely not. Nothing requires anything.

IS: So you can have any combination, such as an undarted jacket and pleated pants, or a darted jacket with plain-front pants, and cuffs or no cuffs on the trousers?

PW: Absolutely.

IS: There’s no need to follow any orthodoxy.

PW: Not anymore.

IS: What do you personally like to wear?

PW: The dog part of my tie business is big business, so I almost always wear a dog tie, because I want people to see it and talk about it. It gives me a chance to make a presentation. Right now I’m wearing a tie with a montage of different dogs. I wear suspenders a lot, because they make pants fit better. I have a number of sports jackets that are wild, but mostly I’m wearing a blue blazer.

IS: How is it cut?

PW: Even way back when, I always did my jackets slightly fitted with a dart. I also like side vents and peak lapels.

IS: It sounds like there’s an English influence.

PW: Yes, except that the English stuff is stiffer than ours. Their stuff has square or roped shoulders, and I’ve never done that.

IS: So you like a natural shoulder with peak lapels and side vents?

PW: Yes.

IS: What about shirts, trousers and shoes?

PW: I wear solid oxford-cloth buttondowns most of the time. When I went to school, one of my signatures was pink buttondowns, and back then that was considered very edgy. In 1958, if you wore a pink oxford you almost needed to be ready to defend yourself. I don’t like French cuffs because they’re just another thing you can do without. With a blazer, I’ll wear gray flannels or khakis.

For shoes I have penny loafers. Until about five or 10 years after my father died I had never bought a pair of shoes in my life. When I joined my father our shoe size was the same, and he would have three pairs of custom shoes made every year by Peal. He’d wear them for three years and then give them to me. My dress pumps are still my father’s because I’ve never worn them out.

IS: So you’ll wear a buttondown collar with a peak-lapeled jacket?

PW: Sure.

IS: Doesn’t that go against all the rule books?

PW: I’m not worried about the rules. I used to wear pink oxford buttondowns under my tuxedo. Then my father said, “You really shouldn’t be wearing a buttondown. If you want to wear pink, make pink tuxedo shirts.” So I did.

IS: What do you enjoy about tailoring?

PW: The people. We were privileged to deal with such an amazingly interesting group of customers, and still are today.

IS: What would you most like Chipp to be remembered for?

PW: That we turned out very good, very honest clothing that represented good value. We never said we thought our prices were inexpensive, but we have always been very honest and tried to give individual customers what they wanted, and were not so self-centered to think that we were the final arbiters of what was right and wrong, or that what I personally like to wear is what everyone should wear.

IS: What do you make of the growing prevalence casual dress over the past few decades?

PW: It’s like a plague of locusts. It has killed the men’s clothing business. A lot of really fine stores are out of business. A lot of customers I have, who have the most stripes on their sleeves at their law firms, bitch and moan that if they want to attract young people out of law school, they have to allow dressing down, even if they absolutely abhor it.

I had a customer come in once who almost had smoke coming out of his ears. He was the chairman of a very big bank, and told me that the CEO and CFO had a special meeting with him on a Saturday to talk about a $100 million line of credit, and they came in wearing sneakers and greasy pants, as if they’d been working on their boat. And he was appalled that they wouldn’t give the meeting more respect.

I think things are changing, but will it ever go back to the way it was? Not in my lifetime.

Winston image via the New York Times.

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