Finding the Right Tailor

For men who spend any time browsing style blogs and forums, this is almost a throw away statement. Every author and his dog has told his readers that a key to dialing in his style is establishing a relationship with the right tailor.

But what does that mean exactly? I know I’ve used a total of four different tailors in the last decade. While all of them were similarly competent in their skill levels, there’s a reason I’m currently using the one I am.

The ability to tailor should be a default, not a bonus. Unless the tailor a man uses has only been open for six months or has an eerily quiet shop, it’s safe to assume he knows what he’s doing. This is not a plus, it’s an expectation. I have yet to visit an incapable tailor, so don’t get too excited about the prospect that he’s capable.

With that out of the way, there are three key things to look for when establishing a relationship with a great tailor. His fairness, his taste, and his willingness to meet your expectations.


Fairness should be obvious. It doesn’t matter how well he does, if it’s $200 to bring the sleeves up on a jacket, he’s overcharging. Ideally, a man’s tailor should be willing to address each need of a garment, break it down by its effect and priority, and then give a corresponding price breakdown.

This morning I met with a man who had a jacket that was too long in the body, too wide and too long through the sleeves, too big in the chest, too large in the shoulders, too large in the waist, and too big through the back. All in all, it was huge on him. Unfortunately he needs it for a business trip in a week, so going the custom route isn’t going to work and he’s had the suit for a decade, so a return isn’t an option. I sent him to my tailor with the understanding that she would prioritize each item for him according to its effect. For example:

Shorten the jacket

Bring in the shoulders

Shorten the sleeves

Decrease sleeve circumference

Decrease circumference through waist

Decrease circumference through chest

Decrease circumference through seat

Bring in back.

Her order might not be the same as mine, but it will be similar. Secondly, she’ll tell him that shortening the jacket is impossible to do and bringing int he shoulders will most likely cost him as much as it did to purchase the jacket. If he wants to pay for that, he can and can now do so with the full knowledge of both its price and importance. From there, she’ll break it down and let him decide if he wants to pay for any or all of the alterable details.


Taste is another huge aspect. When it comes to clothing – and certainly to menswear – there are very few things that are objectively bad. Finding a tailor who sees clothing with a variable lens makes the communication process much simpler.

This doesn’t mean it’s necessary to find a tailor who dresses exactly as one wishes. However, it is key to find who is capable of understanding the desired goals and what steps are necessary in order to accomplish them.

In my opinion his willingness to meet his clients’ expectations is the biggest differentiator between an ok tailor and a great one.  The last thing a man needs is a tailor who will argue with, talk down to, or belittle his expectations.


I remember going in to buy my first real suit more than 10 years ago and wanting something with a higher rise. This was 2003, long before slimmer suits had started to gather steam and I was wanting something that fit more like my jeans than what I’d been wearing to church each week for years. While I was out shopping, each sales person and in-house tailor told me it was impossible to find and/or alter a pair of suit pants to fit the way I wanted to and, if I wanted a rise that didn’t sink to my knees, then I needed to wear my suits up at my navel.

I look back now and don’t see an objective impossibility as much as an unwillingness to push themselves out of their comfort zones or their expectations of what good style is.

My current tailor doesn’t just tell me what I want to hear; she helps me see the ramifications, difficulties, or expenses in making changes. But, at the end of the day, if it’s possible and I’m willing to pay for it, she’ll do whatever I want to get the job done.

A tailor should be an advisor, not a competitor.