If you had to start over again, where would you begin and which tailor would you pick?

[HristoStefanov]

If I had to start over again, then I would order a dark navy suit from a cheaper neapolitan tailor - for exampe from Sartoria Granata (true bespoke, hand made, very good price) and then focus on bespoke shoes and I would maybe save my money and skip all other "dandy" garments.

Explanation:
-> A good dark navy bespoke suit is a must have. Don't be obsessed with perfection. Small imperfections are ok.
-> Substituting RTW shoes for bespoke shoes improves greatly your comfort and improves your casual looks in a subtle way.
-> All other garments like odd jackets ect. are more or less optional and I could live without them if I have other priorities and financial restrictions.

Please don't kill me for this oppinion. I am just answering the question with honesty. While it was fun to experiment with many bespoke garments and tailors and it was fun to stand out in the crowd by being often the only person with a jacket, this has some disadvantages as well.
1. On a psychological level you separate yourself from other people when they can't relate to you because of your more dandyisch appearence. So sometimes it is better to be dressed as the crowd. Sometimes it is beneficial to be a relatable person.
2. I would have been glad to have the maybe 20k EUR I have spent experimenting with bespoke garments on my bank account as a free capital ready for investments or as a financial cushion in turbulent times (like these).

[davidhuh]

Dear Hristo,

overall good thoughts - allow me to comment below

If I had to start over again, then I would order a dark navy suit from a cheaper neapolitan tailor - for exampe from Sartoria Granata (true bespoke, hand made, very good price) and then focus on bespoke shoes and I would maybe save my money and skip all other "dandy" garments.

Explanation:
-> A good dark navy bespoke suit is a must have. Don't be obsessed with perfection. Small imperfections are ok.

Oh yes, and yes. Why is the message so difficult to convey? The dark navy is the most versatile staple suit for anybody, followed by the dark grey. Every reasonable tailor will tell his clients.. Nevertheless, most won't listen.

-> Substituting RTW shoes for bespoke shoes improves greatly your comfort and improves your casual looks in a subtle way.

I would disagree on this one, and invest on several pairs of good RTW shoes instead. All one has to do is find an RTW shoe maker of good quality fitting ones feet. I would not invest in bespoke shoes before having 5 summer suits and 5 winter suits in my wardrobe, plus a few sports coats and an overcoat or two. Once this foundation is led, yes, of course.
The reason is simple: unless a man requires orthopaedic shoes, a bespoke shoe will add less perceived value to ones appearance and comfort than bespoke suits and coats.

-> All other garments like odd jackets ect. are more or less optional and I could live without them if I have other priorities and financial restrictions.

This is a matter of taste and life style. To me, having some tweed coats would be as much a necessity than having the dark blue and the dark grey suits - in fact, it would be my third investment into bespoke, with half a dozen grey flannel trousers.

Please don't kill me for this oppinion. I am just answering the question with honesty. While it was fun to experiment with many bespoke garments and tailors and it was fun to stand out in the crowd by being often the only person with a jacket, this has some disadvantages as well.
1. On a psychological level you separate yourself from other people when they can't relate to you because of your more dandyisch appearence. So sometimes it is better to be dressed as the crowd. Sometimes it is beneficial to be a relatable person.

This is a good observation. When a man turns into bespoke, people will notice sooner or later. The more discreet the first garments, the less they will notice, and the wearer will grow and feel at ease with this way to dress. It is difficult to stand out wearing a blue coat and grey trousers... But this message is difficult to accept for a novice.

2. I would have been glad to have the maybe 20k EUR I have spent experimenting with bespoke garments on my bank account as a free capital ready for investments or as a financial cushion in turbulent times (like these).

Me and my bank would also be glad to have avoided some mistakes in my early choices, but so be it - it is also an effective way to learn by experience. Making mistakes, going wrong but learning from it is the way to heaven

Cheers, David

[couch]

2. I would have been glad to have the maybe 20k EUR I have spent experimenting with bespoke garments on my bank account as a free capital ready for investments or as a financial cushion in turbulent times (like these).

My first bespoke garment was a dressy dark navy blazer in worsted flannel, commissioned when I was 30. Probably the most versatile possible garment for a younger man in a creative field. Nobody in those days looked askance. At the time I expected it to be a once-in-a-lifetime indulgence—and in 1984 bespoke prices were (in constant £) nowhere near what they are now, especially with a favorable USD exchange rate. I didn't feel able to begin devoting some resources to bespoke again until twenty years later.

It's an irony that applies to many things in life that the best time to experiment, develop one's individual taste, and establish relationships with tailors (or other experts) is for many of us also the time when we are still building a financial and logistical foundation, and thus the most constrained. I feel fortunate that there are still enough craftspeople and (thanks in large part to the Cloth Club) materials left to find a congenial bespoke relationship as a more mature customer. By this point I dress largely to satisfy myself, which was harder when younger. And if one is going to be with people who are likely to be distanced by bespoke attire, and it matters to you, one can always dress down for the occasion.

[HristoStefanov]

I would disagree on this one, and invest on several pairs of good RTW shoes instead.

Thank you, David! Great post!

Sure, let them be RTW shoes if you find a last that satisfies you.

My point is that most people with benefit more by several pairs of higher quality shoes than by other garments like odd jackets.
The reason is that one could wear a pair of great shoes with his old jeans and with a shirt without a coat.
This is already a huge step towards a better style and for really a lot of settings and people would be an acceptable look. This is especially true for people in the age of for example 25.

So:
Step 1: A navy suit.
Step 2: Several pairs of high quality shoes.

If someone cannot afford to immediately continue expanding his wardrobe, then I think it is perfectly acceptable for most people to make a pause here for some months or years until they could more easily afford to spend on odd coats, trousers, and for a suit diversity.

Even then I am not sure, that the third step would be for all people the same. Honestly for many young people it might make more sense to continue with some great go to hell trousers than with odd jackets.
There a two reasons for that:
1. The jump from a jeans+shirt combo to trousers+shirt combo is less radical than from a jeans+shirt combo to a jeans+shirt+blazer combo or a gray trousers+shirt+blazer combo. This would be especially true for people under 30.
2. The perception and messages that one communicates with the outfit are different. Gray trousers and a blazer is a conservative message and most people don't perceive it as youthful, joyful, fun, and approachable. Especially true for people under 30. Interesting trousers on the other hand are a style statement which in most settings would be both acceptable and perceived as joyful, fun, and approachable.

[couch]

Even then I am not sure, that the third step would be for all people the same.

I think this is the heart of the matter. What one wants from one's clothes does and should reflect the individual. As Michael often says, the man should wear the clothes and not the clothes the man. Each person's social context, stage in life, and more importantly their developing sense of what best presents their essence or personal style, will differ.

I presume the original poster is simply looking for some lessons learned from a variety of members, and your observations provide a very useful perspective. Though I'm not sure approachable go-to-hell trousers necessarily imply bespoke.

[HristoStefanov]

Precisely, thank you!

I'm not sure approachable go-to-hell trousers necessarily imply bespoke.

As with the shoes, of course. It is only my personal prefference to have an insanely minimalistic, but mostly bespoke wardrobe. Other people could be served well by RTW offerings.

[alden]

2. The perception and messages that one communicates with the outfit are different. Gray trousers and a blazer is a conservative message and most people don't perceive it as youthful, joyful, fun, and approachable. Especially true for people under 30. Interesting trousers on the other hand are a style statement which in most settings would be both acceptable and perceived as joyful, fun, and approachable.

If you are “youthful, joyful, fun, and approachable”, you can wear a green Glad bag and your youthful, joyful, fun, and approachable self will come through and delight others. If you are worrisome, self obsessed, dreary and negative, not all the King’s tailors can do anything to stop you from boring and oppressing everyone and everything around you including small children, and cats.

It is completely and inexorably self reducing to think that clothing can either hinder or help you be something you are not. Clothing, at best, can focus the essence of you. It can never modify you, for the good or the bad or the ugly.

You separate yourself from other people when they can't relate to you because of your more dandyisch appearence.”

I almost always dressed differently from anyone I knew or wanted to know. It never harmed me. It never helped me. And, more importantly, I never lost a moments sleep over it. If you feel like you are living separated from other people or that they can’t relate to you, look far afield from your dress, something else is going on and it’s going on in you.

I had these conversations with my Grandfather and he had them with his Grandfather. Every generation is convinced that their generation is so unique and yet we live on a great cosmic Ferris wheel that spins round and round but never advances even a meter. In the turbulent late 60s and 70s “wild, groovy trousers” were the obvious solution to our dressing woes. Yep, they sure were…ask your Grandfather.

Cheers

[alden]

How I would start over would depend on the fabrics I could find of sufficient quality. I would look for cloth for a blue suit and a gray one with two trousers, a tweed jacket and a 3/4 coat in blue or gray. I would use my tailor

[andy57]

1. On a psychological level you separate yourself from other people when they can't relate to you because of your more dandyisch appearence. So sometimes it is better to be dressed as the crowd. Sometimes it is beneficial to be a relatable person.

I have never felt this way.

I do not want to be the guy looking at someone else and admiring how he was dressed but wishing that "I could pull that off". That's why I experiment. As with all experiments, some succeed, some fail. Better that than never to try at all. I also think that clothes tell a story, or perhaps it's better said that clothes help us tell the story we wish to tell that day.

[Luca]

Hear, hear.

[HristoStefanov]

Don't you think that there is a chance, that we tend to fall into a wishful thinking trap on this matter?
It is very nice to wish and believe that we are not perceived and treated differently because of our appearence, but maybe we are perceived differently.
Don't forget, that the method that YOU apply on how to judge other people is not necessarily the method that other people apply to judge you.
You might not judge people differently on skin colour, sex, origin ect. but other people could judge on such traits. Why would you beleive that it is different for clothes?

Your personality would eventually modify the first impression over time, but there will be a time frame in which your personality has not been perceived yet. I am talking about exactly that time frame and not about exagerated situations when you are boring and oppressing cats regardless of your clothes.

[Anikolov1]

I would agree with Hristo on appearances and not drawing too much attention and not appearing to take yourself too seriously or holding yourself aloof. I think our view is somewhat based on our country of origin. The culture is very casual and if I am with a jacket, I am the most dressed up person. I feel most comfortable with a suit or at least a jacket and I think I picked it up in London, but people are always intimidated by this, even if in our sartorial “world” it’s the most casual dress. There are essentially no black tie events except at embassies with official delegations. I never discuss my clothes because it’s quite unacceptable the amounts we spend on clothes, it is often around an average salary for a whole year which in some ways I do find a repulsive and prefer to be dressed up when I am in London rather than Eastern Europe. I feel we don’t have the tradition in not feeling guilty that our lives are better than the rest and we can afford these luxuries.

It’s also a subject I have no one to discuss with in real life as most people I am in contact with can’t afford it or even if they do, they don’t understand it. They want fast replaceable fashion and new clothes. I hate new clothes and feel comfortable in my clothes only I have worn them for sometime.

In the beginning I did start quite aggressively to spend and got Several bespoke garments in a very short period but I have been largely disappointed with them even if they were from reputable high end makers. I do believe that with time I developed the eye for proportion and problems and the process has become much better. I am stopping myself a bit because I have found that the suits and jackets I use a lot less now than I did in London. Bespoke shoes were my biggest disappointment. Although beautiful, my Stefano Bemer are compromised in fit, they are essentially not better than my RTW, although 3-4x the cost. I have also been somewhat disappointed with Neapolitan trouser makers as they want to cut a modern tight silhouette and I want classic old English style. Right now I am only spending on LL cloth as I value the designs and quality and will be able to have them made up a bit later.

[andy57]

Don't you think that there is a chance, that we tend to fall into a wishful thinking trap on this matter?
It is very nice to wish and believe that we are not perceived and treated differently because of our appearence, but maybe we are perceived differently.

It's not that I believe I am not perceived differently (although the question presents itself: differently than who?). It's that I don't care.

[HristoStefanov]

It's that I don't care.

On the one side it is very good to be independent from other people's oppinion. Definitively! It is very important for your personal happiness and this is a mindset of strength and leadership.
On the other side there might be some value in being empathetic with the thoughts and feelings of others. The "I don't care" mindset is not exactly a social and empathetic mindset.

I would throw another thought in this topic: What is a dress code?
Isn't it a convention that helps you to mingle in the crowd in a particular setting?
You receive the information about the dress code in the invitation in order to show up in a dress similar to the dress of the other participants.
There might be a reason for this. People in the past were not stupid. They knew that there is a value in this mingling and in similarity. People that are similar might come easier in a conversation than people who are very different.
Dress is a tool. It might be a tool to tell a story. It might be a tool to make a statement, it might be a tool to break the ice by saying - "Hey, I am like you! Why not having a chat with each other?".
By ignoring these properties of dress, you are just throwing away another tool that might be useful in life.
If you want to win somebody, show similarity.
If you want to demonstrate power, come with a dress that is a statement. Come in jeans to a black tie party to tell "I am so important, that I can afford to do that and nobody could afford to throw me away". Come in a suit to a casual setting. A tool in a toolbox.

[andy57]

It's that I don't care.

On the one side it is very good to be independent from other people's oppinion. Definitively! It is very important for your personal happiness and this is a mindset of strength and leadership.
On the other side there might be some value in being empathetic with the thoughts and feelings of others. The "I don't care" mindset is not exactly a social and empathetic mindset.

If that mindset were to extend to things other than how I choose to dress when I leave my house (and people who know me might opine that it does, though I hope not) you might have a point. But when it comes to how I choose to dress, there is only one person whose opinion matters to me and that person is my wife.

I would throw another thought in this topic: What is a dress code?
Isn't it a convention that helps you to mingle in the crowd in a particular setting?
You receive the information about the dress code in the invitation in order to show up in a dress similar to the dress of the other participants.
There might be a reason for this. People in the past were not stupid. They knew that there is a value in this mingling and in similarity. People that are similar might come easier in a conversation than people who are very different.

Dress codes, such as on an invitation, are very useful, I think. I would not attend a wedding, for example, in some attempt to upstage anyone. I think that would be extraordinarily rude. But, absent a specified dress code I would wear (and have worn) a dark suit, white shirt, and a silver or grey tie, and black shoes. On occasions like that, one honors the occasion. Believe it or not, there are people who appreciate it when someone, by their appearance, seems to have made an effort to dress nicely.

Dress is a tool. It might be a tool to tell a story. It might be a tool to make a statement, it might be a tool to break the ice by saying - "Hey, I am like you! Why not having a chat with each other?".

The idea that one's clothes tell a story, is, I believe, essentially the point I made earlier.

By ignoring these properties of dress, you are just throwing away another tool that might be useful in life.
If you want to win somebody, show similarity.
If you want to demonstrate power, come with a dress that is a statement. Come in jeans to a black tie party to tell "I am so important, that I can afford to do that and nobody could afford to throw me away". Come in a suit to a casual setting. A tool in a toolbox.

If I go to a wedding I dress in a suit, if I go to a rugby match or a baseball game I will wear jeans and a bomber-style jacket of some sort. If I am out and about in San Francisco, New York, Florence, or London, I will dress however I please. And if that means I'll be wearing a suit and tie when all around me are in shorts and t-shirts, so be it. And why would I care what such people might think of me?