At a certain point most men (at least most men reading this website) think about going to a tailor. They’re getting married and want a real suit. They have a job that requires a formal approach and want to graduate to the next level of tailoring. Or they have just decided to get to know the tailoring process—which is a great idea. 

It’s a big decision. It’s an investment of time and money for a suit that’s going to make an impression and last for years afterward. And it’s even trickier since there are so many possibilities and not always a lot of clear answers. I get asked about this a lot and here are some thoughts that I hope will get you into the right place. 

Essentially, I think you’re trying to find well-made clothes at a good price that fit your temperament. Unless you are at the highest levels of tailoring (Savile Row or certain places in Italy), it is not likely that you will be able to visit the workshop where the craftsmen and -women work. Those places are rare and very expensive, but many places in cities like New York will work closely with a factory in Italy, and there’s nothing wrong with that. 

Anytime you’re visiting a tailor I would recommend making an appointment. Call ahead, tell them roughly what you’re looking for, set a time. This will prepare them, they might set fabrics out for you. If you have a coat that you love I would bring that. Or a photo of something from their site. That will make things much easier than if you march in off the street. 

1/ Know what you need. A suit for a wedding is going to be dressy, a fine fabric, and not something you would wear to work. A suit or sport coat that is more versatile has more texture and can be more daring. I generally think it’s good to have something you can wear a lot. If it’s not for your wedding I would think about a three-season sport coat or a lightweight grey flannel or worsted suit.  

2/ Know what a tailor does well. Tailors have their own house style. Most English suits will have more structure in their chest (as opposed to a more natural, softer chest). This can surprise many American men who’ve never encountered that before. The shoulder can be natural (more Italian) or built up. Read their website beforehand or ask them about it (or just look at the men who are working there). The house style can be very insistent—I went to a Savile Row tailor who refused to make my trousers without a break. 

3/ Know your terms. The word bespoke is so overused it’s lost its meaning. A true bespoke suit is made from a paper pattern cut for you, completely to your specifications. It’s a bench-made, completely by hand with no (or very little) machine work. Do you need a bespoke suit? Probably not. They are fiercely expensive, usually north of $5000. And, unless you have a very specific body type then some version of made-to-measure should be fine. I love the process of having a suit made by hand, it’s a special tradition and it’s great to be part of it. But not every suit has to be bench-made. 

4/ Know the house pattern. So that leaves a made-to-measure suit or jacket. Let’s focus on the jacket. A good tailor will have developed his own pattern and usually works closely with a factory in Italy, where most tailored clothing is produced. Does the tailor work closely with the factory? Do they do a lot of made-to-measure clothes? Or are they a brand whose focus is elsewhere? At most tailors you will try on a sample jacket and then be measured against the one that fits you best. A tailor that does this a lot will measure you confidently and tell you what to expect—it’s what they do. If you don’t like their sample jacket that is not a good sign.

5/ Talk to them about the process. A good tailor will be proud of every step of what they do and be happy to walk you through it. They’ll tell you where the jacket is made. They’ll be confident when it will be delivered. They’ll work well with their in-house tailor who will be making final adjustments. 

6/ Think long term. A good tailor will have an idea about what will wear well over time. They will steer you away from fabrics that are hard to wear or overly delicate. Do you want loud details, like liners or contrast stitching? No, you do not. They will quickly exhaust you. A good grey flannel suit. An unstructured blue sport coat that’s slightly more luxurious than it has to be. These are good places to start. 

7/ If you see something you like at the tailor tell them. When you’re talking about wine with a sommelier, the more information you can give them the better. It’s the same with a tailor. You can bring a coat you like that fits you well. You can say that jackets are uncomfortable through the shoulders. A tailor should be curious about your past experiences and what you are looking for in the future. If they are so intimidating that they don’t listen to you then think twice. 

8/ Be honest about what you can pull off. You want to dress like the grandson of a famous Neapolitan? Good luck. That takes time and a good bloodline. If you walk out with a tight double-breasted suit it will end up in the far reaches of your closet.

9/ Enjoy the process. A good tailor will teach you so much. It’s a wonderful thing. About how clothes are made, how fabric is woven, and, ultimately, how to pull it all together. There are so many options now (I’ll go into those in a later piece) that you shouldn’t feel miserable. That’s not to say you won’t feel nervous the first time you go in. But that happens anytime you do something important, it shows you care. If all goes well it could be the beginning of a beautiful friendship.