Five Fits With: Yuhei Yamamoto of Ivy Style Outfitter Tailor Caid
I’m thrilled with how the Five Fits universe has grown to include all walks, but at the end of the day, I always keep my humble menswear beginnings in mind. I still get excited to feature those who actually work in the industry, so it is my honor to tell Yuhei Yamamoto’s story this week, along with the story of his delightfully elegant, Ivy-leaning tailoring business, Tailor Caid. I first met Yamamoto-san photographing the man and his wares for our mutual client, the Armoury, here in New York City—the only place in the world in which he does a trunk show.
Yamamoto-san tells me he grew up very mature, admiring adults from an early age. “I was into American and French cinema and American music and jazz since I was really young,” he says. This led him to attend a high school that had an art program, where creativity led him to materialize his passion for the look of the stars of classic American films. In 2001, Yamamoto-san started Tailor Caid, and in February 2002, the tailor shop opened its doors to immediate clients and acclaim. Below, we discuss how he first came to find a passion for tailoring and Ivy style, what makes his tailoring special, some of his favorite brands outside of his own, and more.
Fit One
How did you first find a passion for tailoring and Ivy style?
After graduating high school, I entered an art school studying drawing. It was during the time that I started to get worried that the cool suit styles that I saw in the Golden Age American films—from the ’30s through ’60s—would die out and I wouldn’t be able to wear them by the time I became an adult. This is why I started my apprenticeship under a tailor while I was still studying at art school. I genuinely had a sense of urgency then, which was in the ’80s. I didn’t vibe with the suit styles that were popular around the time. I decided that I needed to make suits that carried on the styles that cool guys in those iconic films wore, to preserve this tradition.
I started my own tailoring business 24 years ago. But nothing has changed in me. To this day, I am still the same kid who was fascinated by films and jazz culture. There are lots of people like me in the world, and I get to make tailored clothing for them. It’s truly my calling. I have a strong sense of mission to preserve this tradition. I believe that it is especially meaningful to Japanese people like me to create something that has roots in other parts of the world that we are fascinated by—in my case America and Europe. It is a unique creative process of making our fascination into something tangible. I never want to lose this side of myself. I never want to lose this romantic feeling towards this culture and tradition. I want to share that feeling with my clients and incorporate it into my creations.
My approach is not all about fashion. It is driven by appreciation to culture. What I notice nowadays is convenience has become the value that governs this world. Be it fast fashion or fast food, it’s all about speed and efficiency. On the other hand, for me and what I do, it is most important to take time and effort and create beautiful things in a traditional way that has been passed down to us for years and conserve this tradition for the next generation.
Fit Two
What makes Tailor Caid special? And do you have any tips for wearing tailoring without looking out of place? You’re a refined older man, but it might be hard to wear Ivy style convincingly if you’re a younger guy.
Trend may dictate popular silhouettes and cuts at any given time, but every person has their own golden ratio that cannot be affected by trends. Finding the golden ratio that each one of us uniquely has is something that I care about the most. As you could see in my five looks, four suits out of five are the same style, except for the seersucker suit. To build our own lifelong wardrobe using the same suit style—made with an individual golden ratio but making each iteration with a variety of different fabrics that accommodates each season—is in fact a very fun journey. I only wear white shirts. This is a choice I came to refine after many years of experimenting. I also wear solid ties most of the time. My sartorial sense has always been influenced by older generations. It is about embracing aging. Nowadays, everyone tries to look younger. As we get older, society tells us to look and dress younger. My philosophy at Tailor Caid is the total opposite. We embrace maturing. It doesn’t matter if you are in your 30s or 50s. You are in a process of maturing in your own way, like a good vintage piece. We think that as we age, we become less relevant to trends and what is happening in society. But with classic tailoring, it’s the opposite. We look better in our tailoring as we age as long as we understand and embrace our golden ratio.
Fit Three
What’s it been like building your business and client base?
I clearly remember the first day and the first client. I was so worried if anyone would ever come. There was a small article covering the opening of our shop in a men’s fashion magazine, so it wasn’t completely unknown. We ended up having a lot of clients on the first day. The first person came in right after I opened the shop. He was a young lawyer. From the beginning, one thing that is unique about Tailor Caid is the fact that my clients get along very well. They meet there and become good friends; they hang out to get some food or drinks. Tailor Caid has become a little society. Luckily, I have been featured in various media in my career and they make it seem like I am bigger than what I actually am, but I always consider myself a local tailor. No matter how internationally known Caid becomes, the relationship with my local clients who came and supported early on is the basis of my business.
Because of their continuous support and trust, my business was able to survive the hard times like the Lehman shock, Covid, or the earthquake in 2011. Even when the things were tough, my clients still showed up at my shop and placed orders. I can never forget this. My dream is to do business with people who share the same wavelength as me. I want to have steady growth, not drastic growth. It is not about money at all for me. It’s wonderful to surround myself with people who have good vibrations. I get a lot of inquiries about hosting my trunk shows all over the world, but I only work with the Armoury in New York City. If I was chasing money, I would have done more trunk shows, but to me, relationships are more important. We’ve worked very well together for 11 years. Bespoke tailoring is not about selling items on the spot. It takes time, and it’s very expensive. And you need to deal with difficult tailors like me! This is a very intense process. If I were to expand my business and do more trunk shows in different places, my life will end up in total chaos.
Fit Four
Do you wear any other brands?
Coherence, my friend’s brand, and vintage items. I used to buy so many vintage pieces when I was younger, but it got out of hand, so I stopped buying. I really love the idea of building a wardrobe with staples that American traditional retailers such as Brooks Brothers and J. Press were known for. It is a certain attitude, routine, or lifestyle for men not really interested in fashion that I really admired. These retailers sold basic items catered to this kind of lifestyle at an affordable price point. The products that Brooks Brothers offered up until the ’80s were exceptionally good. I remember seeing them at the shop in person and thinking to myself, Wow, these are truly cool.
Fit Five
Can you recommend a favorite place in Japan?
Jinbocho in Tokyo. It is an old neighborhood for vintage books, magazines, and other printed matters. Everyone there is on a mission to look for specific things they want to study, so there is a certain serenity and calm there. There is no chaos like in Shibuya or Harajuku. I must visit there at least once a week to recharge my cultural energy. I get a book and go to a café for a cup of coffee. I took one of my American friends there and he loved it so much he wanted an office there. It even feels like the time passes more slowly there, even if it is located in the middle of Tokyo.
If you had to wear one outfit for the rest of your life, what would it consist of?
Donegal-tweed three-piece suit with knit polo, black Alden shoes, and for a watch, do I need to choose one? I have three: Cartier Tank, Patek Philippe 3796, Rolex GMT Master 1675. These will cover all of my needs. I like a small watch, not big watches that are in trend. I only like to show a bit of my watch from the sleeve.
esquire
