Jim Winston Remembers Chipp

Ivy-Style has featured several posts about tailor Paul Winston, who worked at his family’s legendary clothier Chipp from the ’60s to the ’80s.

Now we’ll hear from Paul’s brother Jim, a sexegenerian blogger based in Connecticut whose site is called Summer of Jim, and who also spent a quarter of a century at his family’s shop located at 44th and Madison in New York.

In one post, a book review sets Jim reminiscing about his days at Chipp. Here are some excerpts:

I worked at Chipp for 25 years with Paul. Our ideas in taste we acquired through Dad [Sidney Winston], his taste coming from his days as a salesman at J. Press in New Haven, home to not only J. Press, but also Arthur M. Rosenberg, Fenn Feinstein and Langrock. This was the epicenter of “Ivy League Clothing,” when to dress Ivy League meant hand-loomed shetland sportcoats, worsted flannels, oxford buttondowns, rep striped ties and shined loafers.

It’s somewhat ironic that this clutch of stores that catered to the WASP aristocracy in America who attended Yale, Harvard, Dartmouth, etc., were all owned by Jews. My Dad would tell me, “We’re their lawyers, their doctors, their accountants and their clothiers.” Surely an oversimplification and not uniformly accurate, but it did have a ring to it.

Later, this wonderful description of the eclectic dressing sense of Old Money types:

I’m still thinking about those years with Paul and [brother-in-law] Alan. Thinking about how to my eye today’s clothing quality and taste has dropped down the toilet. We have replaced sound workmanship that had enduring appeal with slick appearance made with no substance. We used to enjoy the sight of a customer coming into Chipp wearing a venerable tweed jacket that he had tailored in 1954, with a pair of India Whipcord trousers that was purchased in 1965, a buff-coloured hunt vest made in 1924 for his grandfather, an Atkinson poplin tie in the Argyll & Sutherland stripe that he purchased on sale the previous July, and an oxford shirt slightly frayed at the cuff.

It all worked: Articles of clothing, spanning 45+ years, yet coming from a central core of style and taste that made the appearance timeless. Ralph Lauren has built his business on synthesizing that “timeless” clothing concept and compressing its acquisition to the moment, the clothing equivalent of a convenient TV dinner.

Finally, a snapshot of Jim himself:

I have to laugh. My tailored days are long past. My present-day working kit is khakis or jeans and a t-shirt, a sweatshirt added in the cold months, and boat shoes worn without socks unless there is over an inch of snow or rain.

Oh, I guess I could clean-up okay. It’s just not as much fun as it used to be. And besides, I think “ship wrecked” is a good look for me.

9 Comments on "Jim Winston Remembers Chipp"

  1. Terrific post! What a character… and I love his very specific descriptive recollections. Off to check out his blog…

  2. “the clothing equivalent of a convenient TV dinner”.

    Couldn’t have been expressed more succinctly.

  3. Jim was my go-to guy for many years; now it’s Paul. Chipp forever!!!

  4. Nicholas W | March 25, 2010 at 6:48 pm |

    A real nice read. thanks alot.

  5. Anglophile Trad | May 7, 2017 at 12:20 am |

    Thanks, Christian, for recycling a great old post.
    After seven years, it seems brand-new.

  6. Woah! Check it out…

    Looks like they’re getting ready for Bill Haley and the Comets to come round for a fitting.

  7. Vic Delta | May 8, 2017 at 9:48 am |

    A tasty nugget indeed! Chock full of nutrients and non mots. Within moments of scoping his blog, I got a new recipe and a wine recommend. Totally on board the shipwrecked program. Like a swan dive, best done well by looking effortless.

  8. Love the “ship wrecked” comment.

    Fact: I still own a poplin suit purchased from Chipp in 1988.

  9. Marc Reisinger | August 17, 2022 at 7:50 am |

    I was curious where you got this photo above?

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