Getting him to a tailor: the first appointment, together

For a lot of men, the hardest part of a good suit is walking in the door. A tailor’s studio is unfamiliar, it sounds expensive, and it feels like a place where someone will judge his shape. The easiest way past all of that is to go together, for a reason, with no pressure to decide anything on the day.

This is part of helping him dress better, the guide for her.

What actually happens

It helps to tell him exactly what to expect, because the unknown is most of the reluctance.

• One appointment to start. Sam measures him by hand, they look at cloth together in daylight, and there’s a conversation about what the suit is for and how he likes to wear things. The first appointment costs nothing, and there’s no obligation to order.
• Three to four weeks to make it. Twelve days is possible in a real hurry.
• One fitting, on the finished suit. Back at the studio, the suit goes on, anything that needs moving is marked, and the alterations that get it right are part of the order.

Sam gives one firm price before anything is cut, so there’s no surprise at the end.

Make it an outing, not an errand

Book a time that isn’t squeezed between two other things, and put it around something he’d want to do anyway: lunch, a walk, the drive. Tie it to the occasion: “Let’s get your suit sorted for the wedding” is a plan; “you need a suit” is a chore.

What to bring

• The suit or jacket he likes best, even if it no longer fits. It tells Sam what he’s comfortable in, and that’s the starting point.
• The shoes he’ll wear, so the trousers are set to the right length.
• The shirt he’d wear with it, and anything about the occasion that matters: the invitation’s dress code, the colours of the wedding. What to bring to your first fitting has the full list.

Your part in the room

Sit in, if he’s happy for you to. Talk about the occasion and how you’d like the day to look, and let him choose the cloth. If Sam shortlists two, he’ll usually pick one quickly, and a suit he chose is a suit he’ll wear. Leave the fit to Sam: when the hard truths (the old jacket isn’t worth altering, the shoulders were always wrong) come from the man with the tape measure, they aren’t a disagreement between the two of you.

If he genuinely can’t get away

Then Sam goes to him. Sam comes to his office for the first appointment: the measuring, a selection of cloth and the conversation, without him leaving the building. Book it and choose At your office, and Sam calls to confirm the time and the address. The fitting on the finished suit happens at the studio, where the light and the mirrors are. Does Sam come to you? explains why.

If a whole suit is too big a step

Start with the one he already owns. Sleeves shortened and trousers hemmed on a suit he likes is the gentlest possible first visit, and Sam does alterations on suits, jackets and trousers, whether he made them or not. Once he’s seen what a small change does, the next conversation is easier. If you’d rather it were a surprise, there are ways to do that too.