The bespoke experience of Siniscalchi shirts

Three years ago, I had the great honour of interviewing some of Milan’s finest artisans and style icons for a TV pilot. I visited a shirt maker as part of that show, Alessandro Siniscalchi. I interviewed him about his company’s history, which was founded by his father in 1948, and he showed me his process, walking me through his small showroom and atelier. Then, Alessandro measured me for a shirt, to demonstrate to viewers how it’s done. I was surprised, therefore, as we were packing up that he fully intended to make me the shirt we discussed on camera. [I have since experienced the legendary generosity of Italians a number of times and Alessandro is one of the most generous I have met.]

The thing is, a bespoke shirt requires a number of fittings. Especially with the Siniscalchi method (more on that below). Since shooting the TV pilot almost three years ago, I hadn’t returned to Milan. But that changed this past June when I spent three weeks in Italy. I was able to have my first and second fittings and finally come close to finishing the shirt.

I have known a number of shirt makers over the years and Siniscalchi’s methods are detailed, fastidious, and unique. Alessandro himself explains the process in this unedited clip from the TV show, but I’ll also describe what I experienced.

The first step was measuring and discussing features. Then, (after my delayed return to Milan) Alessandro did a first fitting in muslin cloth, an inexpensive fabric used for fittings. I was surprised how tight this fitting was (I didn’t put on that much weight since my last visit) but Alessandro explained the body of the trial shirt was supposed to be snug, so that he had a three dimensional example of my figure. From that, he could develop the pattern for the shirt (by increasing the size slightly, where necessary). Also, during the first fitting, I was able to see what the collar would look like. Since it, and the cuffs, were made of interlining fabric, they could be drawn upon or cut. Three years ago, I had preferred a more cutaway style of spread collar. Thankfully, I was able to adjust that and, taking some of my own advice, be more moderate and go with a traditional spread collar. At the time, I also wore more double cuff shirts. I decided to keep this one double cuff because I intend to wear it in more dressy situations.

A week later, I returned for a second fitting. This time, the shirt was basted together in the white twill I had chosen. It had a new interlining collar and cuffs but no buttons. This is where the real work began. Alessandro went over every inch of the shirt, eliminating (by pinning) any creases or extra fabric, while also noting where changes would be made to add more fabric, such as under the arms. The collar was rather loose, so that was noted. I was also able to put on a tie and jacket and see how the shirt performed, which allowed for another tweak to remove extra fabric across the chest.

For most shirt makers, that would be it. The final shirt would be made and delivered. But Alessandro has another, unique step, which is where he says the “real bespoke” happens. Now that I’ve received my shirt in Toronto, it isn’t yet finished. I am to wear and wash it several times (typically three or four) then return to the shop once more. At this point, Alessandro will evaluate how the shirt has stretched or shrunk and alter it yet again. He will take the shirt apart, if necessary, and adjust the paper pattern to get it as close to perfect as possible. I hope to be able to return to Milan soon and complete this remarkable process.

All of this comes at a price, of course. Siniscalchi shirts are around €750. And while the craftsmanship is first rate—featuring finely hand made button holes and remarkably thin single needle seams—and the fabric used is some of the finest woven—my shirt is a silky, lightweight 140/2 cotton twill from S.I.C.Tess, one of Italy’s highest quality mills—what you are also paying for is a dedication to exceptional fit. And the decades of experience and knowledge that delivers it.

Until I have the chance to return to Milan and have the shirt finished, I will wear it, of course. And it is a remarkably good shirt. The fit in the body is roomy but slim, with an athletic silhouette. The collar fit is superb, looking snug but feeling comfortable. Once washed, the cuffs feel tight, but this is an easy fix at the final stage.

There are some decisions I made three years ago I would have made differently now, however. For instance, I think a French placket would look cleaner and more elegant than a full placket. And I would have taken Alessandro’s initial advice and had the collar fused, so that the stitching could have been closer to the edge and the collar that much smoother (at the time, I was a little over-obsessed with floating interlinings). And for a bit more comfort, single cuffs instead of double.

But that’s something I will love about this shirt as long as I wear it. It is not only the product of an exceptional artisan, using time honoured methods. It is a time capsule of my own style evolution.