Sack Suit Perfection: An Interview With Japan’s Boston Tailor

On one of my many trips to the mid-century American oasis amid the typical British High Streets, that special place called John Simons, I found a really neat navy blazer that had all the right details: 3/2 button stance, undarted sack fit, patch pockets, two-button cuff, stitched edges, hook vent, and of course, natural shoulders. That was when I discovered Boston Tailor. 

I loved the blazer not only for its incredible details, marveling that the item was not vintage but recently produced, but also for its solid construction. This was made to last. I was also struck by the name of the company, Tailor by Boston, because I’m from Boston. I asked Paul Simons about the company, and he said he knew nothing about them, just that one day the owner walked into the shop with a sample of his work and told him he wanted to sell it there. 

If I was not already intrigued because of the clothing, now I was on a mystery-story-style hunt to get to the bottom of where this jacket came from. I looked online and finally found an outdated webpage, mostly in Japanese, with a caricature of a man dressed in a sack suit proclaiming it was the home of Boston Clothier. Not Tailor by Boston, per se, but close enough. I emailed the address I found and a week later, heard back from owner Ken Yamamoto. 

Mr. Yamamoto is the owner and master tailor behind both Boston Clothier and Tailor by Boston. He inherited the company from his father, also a Japanese master tailor, who started making suits for American GI’s after the war. The following is our interview, which will be presented in two parts today and tomorrow. — TREVOR JONES

* * *

IS: When did you start your company?

KY: My fifth great-grandfather was the eldest son of Yoshidaya in the Kabuki performance, whose name was Kimura, and he appeared in the Yoshidaya Kabuki story in the 1600s in a Yukaku of Osaka. My grandfather grew up in Osaka and married the granddaughter of the founder of the Citizen Watch Company, and my father was born in Tokyo. When my father got older, he was in the business of selling watches, jewelry and glass to Americans after World War ll. After that, he was hired by a Chinese Shanghai tailor, Smiley Chang, at the officer’s club in the US Air Force base. After a while my father began Boston Tailor in 1952 for American customers. In 1970, we branched out into Aoyama, Tokyo. At that time, Boston Tailor had made many American contemporary suits for Soul and R&B dances in the Tokyo nightclub scene. We are still located at the Shibuya store, where we’ve been since 1979.

 IS: Has it always been the Ivy League Look or have you done any other styles?

KY: My job is a tailor which is to make almost any kind of orders required by the customer. Most of the Japanese mods were also my customers as well. I studied sewing and the style of British tailoring by myself. The 1930s drape suit had a revival in Tokyo in the 1990s. Now that boom has left, which was the English straighter cut (including specially made front darts) of the drape suit could only be reproduced at Boston Tailor. After my generation, Japanese clothiers and customers began to have a keener eye for “real” clothes. Also, in the 1990s Japan was the world capital of “real” clothes and jeans. I think the construction of our coat is closer to more traditional UK tailoring, but the details are completely midcentury Ivy style, the same as from my father’s era. So our coats might look more authentic than other sack coats. Of course, all of our ready-made suits and coats are in the Ivy style of model number one sack coat.

 IS: Why Ivy?  

KY: My father took about 100,000 orders from Americans and made almost all kinds of styles, not just Ivy, from 1952 to 1986. Our best seller suit was the Ivy style, American Traditional model and the American Contemporary model at that period. Today, we continue to carry on that legacy.

 IS: What do you like most about that specific style?

KY: The original model number one sack coat was the first coat created by mankind. As tailors, we have been challenged to create a better look than number one sack coat, but we couldn’t. I think the number one sack coat model is already the perfectly completed coat style as a gentlemen’s garment.

IS: What is the difference between Boston Clothier and Tailor by Boston?

KY: Boston Tailor (Tailor by Boston) is a custom tailor who sticks to old-fashioned styles and ideas in Shibuya, Tokyo. At Boston Clothier, located at the front of Yokota US Air Force base in Tokyo, we offer ready-made sack coats, suits, and top coats, which is made by same tailoring process as Boston Tailor.

 IS: You mentioned you started tailoring at 16, which is quite young. How did you get into the business?   

KY: When I was a little boy, almost all the old tailors around me said they started tailoring at 13, since before World War ll. They often told me that if you want to be a good tailor, the younger you start the better you will be. I did as they told me and succeeded my family business. When I started tailoring, almost every day for the first few years, I just did alterations for the suits. Also during that same period I went to local night high school in Aoyama. Of course, I had man-to-man tailor patterning lessons from my father at the shop during the day. As I recall, I started cutting customers trousers from 17 and was taking shirt orders from 15. There are so many things to learn and practice to become a top tailor. For example, people often say if you want to be a world famous guitarist, you should start playing the guitar between 8 to 13 at the latest. Tailoring is almost the same. 

 IS: What wisdom or knowledge did your father impart to you? 

KY: I was born and brought up as a tailor. Ever since I can remember, I was watching large-sized, American, Ivy style model number one sack coat being made and ordered at our shop during the 1960s. It was a memorable part of my childhood. It may be an old saying, but I watched and learned from my father, from his sincere work with customers.

 IS: Besides your profession, how important are clothes to you?  

KY: If I have to choose between clothes or food, I would choose clothes! It is the most important thing of human happiness, isn’t it? There is proverb called 衣食礼節(e-shoku-reisetu) from ancient China that says “If you had plenty of good clothes and good food, it will help in developing one’s good moral fibers.” If I made it an English saying, it would be “Well fed and good clothes equals well bred.” And I want to add one thing about Japanese Kanji, or characters that come to us from Chinese. In Kanji, 裕 means “wealthy,”  but there is also an additional meaning of 裕, which is “having a plenty of clothes.” Good clothes are associated with wealth and a good life. I understand these words deeply after watching many customers as a tailor for over 40 years.

Part Two

IS: Japanese consumers have a very keen eye when it comes to detail. Does that make your job harder?  

KY: All clothing enthusiasts always want things made to exact specifications, I think Americans do as well. They want “real” clothes, like the way vintage clothes look, such as in old photos or old movies. Some people look for the wrong thing in clothing. For example, they just have keen eye for clothes without a single wrinkle, new and off the rack, which is just like industrial fast fashion. Besides that, as a tailor, I will try to follow and satisfy whatever my customer requests, even if it may be difficult. That is our work.

 IS: What is the current state of Ivy in Japan?

KY: There are so many Ivy enthusiasts for several decades now, but I have never seen Ivy style in the street, so I do not feel I understand why it has come back and became popular now. But I would like to know more about the word “Ivy” in the US. Our American customers used to say, “American Traditional Model” for the Ivy League tailoring style — they did not even say word “Ivy.” I checked with our old retired employee, and even our former American employee, and they told me they did not use the word “Ivy” during the 1960s. They commonly used terms such as “American Traditional,” ”American Natural,” or “University Model,” which also can be seen in ’50s-’70s American tailoring style books. It was difficult for our American customers to understand the meaning of “Ivy” at that time. I did not use “Ivy” either, I used “American Traditional” until the 1980s. Japanese often used to just say “Ivy” for any American Traditional clothes in the 1960s, but there was almost no real Ivy League Look in Japan. Actually, some Japanese might feel embarrassed now to say that they were Ivy in the ’60s because it was the typical mistranslated Japanese Ivy look. It was not real and cool, as it was in those photos from GQ or other American fashion magazines. It’s easy to imagine why Ivy died out shortly afterwards in Japan. Even though those Japanese Ivy wearers thought they were cool, in reality they weren’t. Today, even though customers order an Ivy style coat, as a tailor, I’d still rather call it a sack coat because, in the textbook of 1920s American Tailoring, the coats are referred to as sack coats. 

IS: Many Ivy enthusiasts feel territorial about the look. What do you have to say as someone who helps keep the look alive in another country? 

KY: I just want to say that whole world loves good looking, old American styles — everything looks great! I guess to feel territorial about the look comes from the pride of one’s own country’s history. To put it another way, even if a fully trained American plays Kabuki perfectly, we Japanese will have territorial or unsatisfactory feelings. However, I think many American Ivy enthusiasts would like our clothes. Our sack coat is made by following the inch scale from the old US and UK style of doing things, so American Ivy enthusiasts should not have bad feelings towards the details our coats. It was illegal to use the inch scale in Japan after World War ll, but because we took orders only for American customers, we did not follow that law. So, miraculously, we kept inch-scale tailoring in Japan. And as good as the details are, it’s more important to enjoy wearing them. Japanese tailors learned tailoring in the 1800s from English tailors. I assume English tailoring spread worldwide at that time as well, so tailoring in Japan should share some of the same roots as American tailoring. And the reason why it was possible to keep the look alive in another country was that we took orders of Ivy suits from Japanese Ivy enthusiasts up through the ’90s, when the look was not popular anywhere and people had to order to Ivy clothes from us.  

 IS: I found out about you by seeing one of your sportcoats at John Simons in London. Do you sell anywhere else outside of your own shop? And what about the US?

KY: I’ll think about it for the future, but I’m not sure about the US market. I think that the US is too large to sell clothes from Japan. Since the world is becoming smaller, it might be a better idea for American customers to buy from John Simons in London, because they have accurate information about our garments in English.

IS: A big reason you have remained so under-the-radar is because you have shied away from media attention. Why is that?

KY: It’s amazing; you read my mind! Certainly I would like to have a bigger profile, but on the other hand, I want to be independent. And I think the overload of information from the media has good and bad points. The good thing about remaining under-the-radar is it requires an effort from the person to find good clothes that you could never get by the power of money — you have to do some work. You see how the result of your effort in searching for good clothes lead you to our coats; you could not find us through any media. I used to often appear in the rugged Ivy issues of Free & Easy magazine, which I had sponsored and even wrote over seven pages in the tailoring issue. And I used to sponsor a culture magazine called Tokion from the first issue onwards for a couple of years. It was the first magazine in the world to be half in English and half in Japanese. Those magazines were often read in the US, and I am very glad to be known in the home country of American Ivy enthusiasts.

 IS: What is the future of Ivy in Japan? 

KY: It is going to become more popular in Japan. The sack coat looks very good on our Asian faces. It’s like the Japanese Kimono, without front darts, easy waist shape and the natural-shoulder look. It looks just as good on us. 

 IS: And what does the future for your company look like?  

KY: Companies like mine, still actively keeping alive old-fashioned tailoring, are becoming rarer worldwide. There are only few left doing the same thing. We are seeking chances to increase overseas customers, since the population is decreasing in Japan.

 IS: Where can readers buy your items?

KY: J. Simons  in London and Boston Tailor in Shibuya, Tokyo, as well as Boston Clothier in front of the Tokyo Yokota US Air Force Base. Boston Tailor is in the Shibuya–Aoyama area, which is one of the most popular Tokyo sightseeing areas.

26 Comments on "Sack Suit Perfection: An Interview With Japan’s Boston Tailor"

  1. Evan Everhart | April 9, 2019 at 4:19 pm |

    This is absolutely Fascinating! Thank you for this interview and I am eagerly awaiting the second half! 🙂

  2. Evan Everhart | April 9, 2019 at 4:22 pm |

    Also, this gentleman is quite well turned out! Beautiful clothing, and imminently tasteful!

  3. Hardbopper | April 9, 2019 at 4:39 pm |

    I’d sure like to have a number one, grey Harris herring-bone. That would get a lot of use.

  4. Seven Crowns | April 9, 2019 at 6:25 pm |

    Great photos, of both the gent and his handiwork. This is a fascinating read.

  5. Great stuff!

  6. Grey Flannels | April 10, 2019 at 12:53 am |

    Fascinating reading, indeed.
    That brown herringbone jacket looks perfect.
    My guess is that there’s no waist suppresson.
    One can’t tell from a single photo, but it looks like J Press, Brooks Brooks Brothers , and even O’Connells and the Andover Shop should could learn a lot from Mr. Yamamoto.
    One more reader looking forward to Part Two.

  7. Minimalist Trad | April 10, 2019 at 12:59 am |

    Could we have more information
    about Trevor Jones and about IS
    (the interviewer)?
    Thank you.

  8. Excellent get, Trevor. Here’s a question I hope is asked in part 2: has Yamamoto ever been to Boston?

  9. Very interesting! Yamamoto-san definitely should be a traveling tailor. I think he will pick up many new clients stateside.

  10. Trevor Jones | April 10, 2019 at 10:24 am |

    @Minimalist Trad, what do you want to know? 😉

  11. Cuff Shooter | April 10, 2019 at 10:53 am |

    Thanks for this article. I will definitely stop by their storefront.

  12. Charlottesville | April 10, 2019 at 11:39 am |

    Thank you, Mr. Jones. This was really a great interview. What an interesting perspective on traditional American tailoring. I would love to see one of Mr. Yamamoto’s suits. Alas, I am unlikely to make it to London or Japan any time soon. I am wearing an older Brooks Brothers No. 1 sack suit today in bluish gray sharkskin, and it is by far my favorite style. Glad to know that it is still being made.

  13. Old School Tie | April 10, 2019 at 11:57 am |

    Sorry to be a bore, but it is “eminently”.

  14. Fred Johnson | April 10, 2019 at 12:43 pm |

    To my eye the lapels seem on the narrow side as well as the swelled edges. Is there a standard width for swelled edges?

  15. Charlottesville | April 10, 2019 at 1:44 pm |

    Fred – I think 5/16″ is fairly standard for swelled edges, but 1/4 inch is also fine. I am sure that it varies according to brand, manufacturer, lapel width, personal taste, etc. Southwick uses 5/16″ as I recall and I think that is about what I have on my older Brooks and J. Press sport coats. It is probably much like trouser cuffs, and should be in proportion to the rest of the garment and the wearer. For example, I like 1 5/8″ cuffs, which seems to work for my height. A taller man may prefer 1 3/4″ and a shorter man may want to go with 1 1/2″. Just my 2 cents. It is a matter of personal taste, and I am sure that a good custom tailor like Mr. Yamamoto would be able to give you the width of lapel an swelled edge that you want.

  16. Minimalist Trad | April 10, 2019 at 2:02 pm |

    Trevor Jones,
    Any information at all that you’d care to share.
    Please forgive my ignorance in not realizing that “IS” stood for “Ivy Style”.

  17. Regimental Stripe | April 10, 2019 at 2:16 pm |

    I never heard the term “Ivy” before I discovered this site.
    In the 60s, we always called the style “Ivy League”.
    Perhaps it was the Japanese who created the term by shortening “Ivy League”.

  18. There is period US advertising from Main Street brands using just the term “Ivy” during the heyday.

  19. Outsanding Part 2. Trevor, could you shiny any light on whether any of Boston Clothier’s garments are sold on the John Simons website? I don’t see any there.

  20. Terry O’Reilly | April 11, 2019 at 8:01 pm |

    Great interview! I’ll be in London in a couple weeks; I hope to see some of these products in John Simons.

  21. Trevor Jones | April 11, 2019 at 11:42 pm |

    @Eric, John’s site is only a handful of his own label stuff. When you go into his store, there’s so much more than just his stuff (Boston Tailor, for example). I asked him why he didn’t get that stuff online and he essentially wants the magic to remain in the in-store — rather than online — experience.

  22. Trevor Jones | April 11, 2019 at 11:49 pm |

    @Minimalist Trad, I’m a college junior at Salve Regina University in Newport, RI where I will be living this summer and teaching at the International Tennis Hall of Fame. I’m from Hamilton, MA, a small town 40 mins north of Boston. I came across Boston Tailor while living in London on a semester abroad. Is there anything specific? That’s a really, really broad overview.

  23. Minimalist Trad | April 17, 2019 at 7:08 am |

    Thank you, Mr. Jones, for the details, and for introducing me to Salve Regina.
    Always pleased to learn that there are still college students who know how to dress properly.

  24. Does Yamamoto-san speak English and would you know the starting price for a bespoke suit? As a side note, I read somewhere that Yuhei Yamamoto of Tailor Caid started his career with Boston Tailor. Thank God for the Japanese.

  25. Terry O'Neill | June 30, 2022 at 8:46 am |

    I live in London. I bought a number 1 sack coat from John Simon’s himself about 6 years ago, a lovely mid-brown herringbone, Harris tweed. The last one, the price was a steal. I always wanted a Number 1 blazer but John Simon’s no longer sells Boston Tailor, so I contacted Ken via email. He didn’t have my size available so he told me he’d make me one. After a few weeks of email exchanges with measurements, linings, etc (Ken was sooo helpful & detail conscious) I bit the bullet & ordered. By the time Ken had finished the blazer in March the war in Ukraine (a bit more important than my blazer) had caused havoc with delivery times. It arrived today. I can’t tell you how much I love it. It’s almost too nice to wear! I’ll be going back for trousers. It’s enough to make me want to visit the shop, with a holiday in Japan tagged on. Other Japan-made 50’s/60’s US style clothing (selvedge jeans, tees, cowboy shirts, military based jackets, etc) are so well made, stylish and popular that it’s a puzzle that they are no longer designed & made in the US. Cost doesn’t seem a major issue, well made, long lasting & stylish clothes will always have a market.

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