I thought about what the cue would be and for the longest couldn’t think of one. Even though the suit fits well on this gentleman and the color is perfect, there really isn’t anything else that pops out. He is simply well groomed, nothing spectacular nor dull about it.
But then it occured to me why you would assume he wasn’t a New Yorker, the pleats and cut of his suit which comes off as traditional, american tailoring when all of New York seems to be fascinated with European cuts.
I would simply compliment him on his suit, like I’m sure you have, and take his picture. In this situation, I don’t think there is anything else you can tell him without boring an innocent bystander with fashion talk.
Is this a question or a quiz? I mean, how did you break the ice? I think the tie would be a safe bet (always) and is his shirt subtly patterned? If so, you could talk about how he mixed his shirt & tie patterns…
you can take a subtly/noticeable double take and say, “oh!” and make eye contact with him. Then say, ‘i love your tie (if he is italian say, “mi piace la sua cravata”) then he’ll nod or say thank you proudly, then you can say, “and I love that knot. forgive me, but would you mind if I snapped a photo of you?” then he will say, probably heavily-accented and in barely discernable english, “but of course you may, but hurry for I am late for a meeting/plane/espresso” Then you will snap, shake hands, perhaps exchange business cards, then walk off in opposite directions, the sun shining on both your faces.
It’s definitely the pleated pant. Especially that big open pleat right there. That, in and of itself, demands an approach somewhat like this, “Dear Sir, you are not only flaunting a fabulous suit but you are proudly displaying double pleated pants and in today’s world – nobody wears pleated pants, especially pleated pants that are as old-world as yours.”
if it’s not the tie (and i have no idea how you’d approach someone on that one) i would think that you could tell this person he pulls off the sack suit very youthfully. (at least i *think* it’s a sack…it’s sort of hard to tell from this angle)
I would simply ask him if the he intended the thin end of the tie to be longer than the front – maybe it isn’t from the continual tightening (over the course of a day, my Hermes and Gamo ties end up this way as I continually snug them up) but actually his own personal “style”
Though I guessed earlier that it was the great tie knot, (not the fact that it is tied short, this is not an acceptable reason to approach someone IMHO, for I believe it is tied one inch to short, not the top of the buckle but the bottom of the buckle is correct) So…
There is something rather unique and unusual about the suit you are wearing sir, including the color. Would you mind terrribly if I snapped a picture as I have a wonderful internet weblog dedicated to showing well dressed men and women found on the streets of NYC.
“I’m sorry to bother you sir, but I noticed that you’re wearing a very well tailored pleated suit and not many men here in New York are sporting those these days. Are you from New York? Do you mind if I take your picture for an internet fashion blog that I write for? I promise that this is legitimate and you won’t be exploited in any way. Thanks.”
Dear Scott, I have been a reader of your blog for ~18 months and own/appreciate your book. I have been going through your archives and as I read through these comments I knew the cue and how it would afford you with a method to approach him. I scrolled down the list with anticipation, only to see that you finally revealed the answer (although it seems the subsequent posters didn't get it). Keep up your work-you are for many the most important voice in the world of clothing and style.