In the 60s, platform tennis was the hot game. A tournament was sponsored by a venerable Scotch whiskey maker. The tournament was called The Vat 69 Gold Cup. Chipp was engaged to make jackets and ties for the officials and for the winners of the tournament. The chairman of the company was so pleased by what we made that he arrived in his Rolls to personally thank my dad. My father, who loved everything British and Scottish, chatted briefly with the gentleman and then invited him up to his 5th floor office.

In two previous blogs I related the stories of the creation of our Kama Sutra lining material and my prowess in making novelty athletic supporters. Unbeknown to my father, I had covered a jock with one of the Kama Sutra images and left it on his desk. When my dad and his guest walked into his office, my father was mortified by what he found on his desk. His jovial guest thought it was very funny, so my dad gave him the supporter.

That weekend the British Embassy hosted a party—attended by some members of Congress, a Supreme Court judge, and other “A” list Betway-types—in honor of the Sanderson Chairman. The function was black tie. When everyone had consumed their share of Vat 69, the guest of honor put the supporter on over his dinner suit trousers. The following Monday, the Rolls arrived at 14 East 44th St. The Chairman said he didn’t care what it would cost. He had to have forty of the supporters to send to those who had attended the DC cocktail party.

About two weeks after we had shipped the supporters, we stated getting phone calls:

“This is the office of Senator So and So. The Senator received a gift of an unusual Athletic supporter. The Senator would like to order a dozen of the supporters.”

We got about 20 calls ordering one to two dozen supporters. And thus something I did as a joke turned into an item that was a fitting gift in a number of situations (bachelor parties, for example). In our present incarnation as Winston Tailors, we no longer have enough traffic to be able to buy the minimum order required to get the Bike supporters at the dealer price. As a practical matter, they exist no more.

Winston Tailors is on the 5th floor of the building at 11 East 44th Street, across the street from the building that we owned at 14 East 44th Street.  Most of our original customer base have joined my father in the next realm.  For those still on the planet the fact that we have not strayed far from our birthplace makes it easy for them to remember where we are.

So where do our customers come from? When I last checked, there were very few people who would wander up into buildings to see if there might be a tailor on some upper floor.

There are two main sources of customers: word of mouth and paid advertising on the Internet and the yellow pages. 1. Word of mouth: customers who have dealt with us tell, and some times bring in, friends, business associates, and even relatives.  2.  Advertising: this is interesting because we advertise saying we do alterations. The individuals who respond don’t know us from Adam and have no idea that our real business is making clothing not doing alterations. (We do not have an inflated picture of our  place in the universe; if 1/100th of 1% of the businessmen in NYC know that we made all of President John F. Kennedy’s clothing, I would be amazed.) A man walks into his office and says to his secretary,  “I ripped my trousers. Find me a tailor.” All he cares about is geographic proximity. He rushes over and sees what we do, and some then order clothing at a later date.  But what is also important is he joins the word of mouth brigade.

Because we are small, we don’t need a lot of traffic to be happy.  Because we are custom tailors, we can do complicated alterations. And because we do our alterations in our workroom, we can often do simple alterations the same day. “Build it and they will come.” Do good work for your customers and they will come back!

The great majority of Chipp and Winston Tailors customers may be conservative in their clothing style, but their clothing is not boring. As custom tailors, we have the ability to fashion any type of suit a customer would like. We have customers who have us make models that are very fitted and have shoulders that are square or roped, but most of our customers are looking for the classic natural-shoulder model that was once the staple of Brooks Brothers and J Press. (There is no longer enough demand for the old “Ivy League” model for a broad based company to be able to carry it in any depth. That is what has created the niche for Winston Tailors.)

Although Chipp customers were conservative business men who wanted their clothing cut in the classic natural-shoulder model, they often liked very strong patterns. Large patterns, like the Prince of Wales and Ben Venue, could be found in the closets of many a bank president. Bold colors and trousers with embroidered frogs, pheasants, and ducks were seen on the first tees of the most legendary country clubs. Board meetings were attended by our customers wearing suits with green, wine, or blue stripes rather than staid white pin or white chalk stripes. Our customers have always exhibited confidence in wearing what they liked. Some individuals deny themselves the fun of wearing patterns and colors that are different because they think their friends and associates will say, “Wow, look what so and so is wearing.” I feel a tinge of sadness for them.

Winston Tailors makes two products: bespoke custom clothing and made-to measure clothing. Because we individually cut all the clothing we make, there is often little difference between these two products.  After the cloth has been cut we are at a fork in the road—we can make it in our own workroom, the entire garment made by an individual tailor (bespoke), or we can send it to our made-to-measure maker, who has a production line.

The difference is in the sewing and the canvas that is used. (All of our clothing is made with canvas. ) The sewing in made-to-measure garments is the same as is used in ready-made “rack” clothing, even though there are variations in the cutting. As for a bespoke garment, there is a difference in the softness of the construction, so, even if an individual is a perfect size 40R, there would be a different feel to a bespoke garment cut to that pattern.

Who needs custom bespoke clothing?” The answer is very few individuals. Some individuals have body anomalies that require custom clothing, but we can fit the great majority of men with the way we make made-to-measure clothing.

We have been privileged to serve a distinguished clientele of conservative business and professional gentlemen and women. Our customers were never “flashy”- even those who were Hollywood based. (Once Liberace saw something in one of our windows and purchased it. The salesman who helped him then excitedly called my father to tell him about the sale. My father was very upset by the news. He said if we had something that appealed to Liberace we were doing something wrong.) Conspicuous by their absence will be customers names with many of the entries in the blog. The only names that will be used will be for customers who have passed to that great custom clothing shop in the next realm. There is no mystery to what we have done since our first days. We listen to what our customers want and do our best to deliver it. The common thread among our customers has been that they are secure in what they want. Some have not changed their model for 50 years. Sprinkled among the entries will be “pearls of wisdom” that have been passed to me through the years- some by my father, many by our customers. Since we are dealing with custom and made-to-measure clothing I give you the first “pearl”- Tailoring is an art not a science. Even in the hands of a skilled craftsman the art is a sophisticated form of trial and error.

In 1945 Sidney Winston and Lou Prager opened Chipp of NY,Inc. They had both worked for J Press. The business was financed by Jonas Arnold, who was the proprietore of a men’s shop in Cambridge, MA named Chipp. ( Arnold and the Sill’s brothers were partners in a men’s shop in New Haven, CT. named Chipp. They had a parting of the way and the Sills brothers then called their operation Sills and Arnold moved to Cambridge and continued using the name Chipp.) Arnold suggested that Winston and Prager use the name Chipp for their NYC shop. Through the years many Yale and Harvard men who had traded at the New Haven and Cambridge Chipp shops thought that Chipp of NY, Inc was connected to the shops where they traded during their college years. There never was a business connection between the three shops. This is the answer to the frequently posed question, “Where did the name Chipp come from?”

The metamorphosis of Chipp of NY, Inc to Winston Tailors and the creation of Chipp2 ( our necktie operation and the mother of Chipp2.com, the web site that features our dog breed products) will be continued in future blogs. If any readers have questions about our custom clothing , made-to-measure clothing, or our neckties- dog breed or others, feel free to call and chat- 212 687-0850- Paul Winston

A number of our customers have suggested that I share some of the experiences and things we have learned in the 65 years that we have been doing what we do.  What does the two-headed Chipp 2-Winston Tailors do?  Chipp 2 is a small “corporate identity product ” maker. We make ties and scarves for clubs, alumni groups, schools, companies, etc.  Our website features the products we make that feature dog breeds.  Winston Tailors makes custom and made-to-measure clothing- suits, sports jackets, odd trousers, vests.  We also have an unusual range of shirt fabrics and we make shirts to order.  We have been privileged  to deal with an exciting, conservative (in dress, not necessarily politically)  clientele.  The blog will deal with the history of the “two heads” and with some of the things that have come to pass- for example what it was like making clothing for  President  John F. Kennedy.   Tomorrow’s blog will contain a few stories about the origins of the two entities.