He would have been measured like this. You shouldn't be

This was a question put to me the other day by a friend. He was asking about shoes, but I think it applies equally to suiting, shirts and other items of dress. Hopefully you will find my response interesting.

1 It will not be perfect

Bespoke clothing is a wonderful thing, but the first time you have anything made it won’t be perfect. There are three reasons for this. One, it is handmade, an individual item with minor flaws (or perhaps just characteristics). Without them, it would have been made by a machine. Second, you’re new at this, and chances are you can’t describe the image in your head accurately. Third, so is the craftsman. As good as his first attempt to fit anything to you will be, there will always be something he would like to do different the second time around.

2 Act naturally

This covers the fact that you have to stand naturally when you are being measured – particularly for suit. Laugh, flex your hands, move your feet; try not to look like a man who has just heard the command ‘attention!’ The point also covers the fact that you should consider how you wear your clothes. Don’t buy a Super 140s suit if you go drinking and leave your suit on the floor when you get home. Don’t get super thin soles if you never remember to check whether it’s going to rain before leaving the house.

3 Ignore what people say about other people

Sad as it may be, tailoring and shoemaking are bitchy businesses. Everyone has some form of grudge and everyone is some form of salesman. Never trust a tailor who says he is the only man who can cut a good suit. From the opposite point of view, a cutter once told me: “Someone came in and said he’d been to Caraceni, Anderson & Sheppard, Camps de Luca, Huntsman and Poole, and they were all terrible. He asked me to measure him. I showed him the door. That man will never be satisfied.”

4 Be conservative

This is investment dressing. Investments should be conservative. They need to last the fickle fancies of fashion and – more importantly – they need to last through your personal changes in taste. Get a navy single-breasted suit and a black pair of lace-up shoes. Then get a mid-grey single-breasted suit and a dark brown pair of lace-up shoes. Then blue again for the suit, perhaps double-breasted or a flannel, and another pair of black shoes, perhaps a Derby. Ties and socks are much easier to swap than suits and shoes. And a navy suit can be Italian classicist or American prep, depending on what you wear it with.

5 Do it

I once saw someone comment on a forum that he was interested in discussions about bespoke, but was never going to do it himself. The results appeared to be too volatile, given the money. Ignore forums. They are talking over minutiae. They are never going to spend pages talking about the fact that all the bespoke suits they are comparing make them look better than 99% of men in the world. Because it’s obvious, a given. They’ve all accepted that and moved on to discuss the Tautz lapel. If you like the idea of bespoke and can afford it, then do it. You won’t regret it. People will always have one tiny thing they dislike about your suit. But it’s not theirs. It’s yours.

Simon Crompton is the author of Permanent Style