Good question. I would probably send you to a friend of mine who runs a tailoring shop. He can give you better answers.

And honestly, I think most of the city would view that as a challenge more than anything. I'd stay away from anything that is fetishwear, any leather or latex outfits. I lean towards a suit myself.

[He turns to the rack to try and find a shirt that buttons up a bit more than the one the man is holding and a matching blazer.]

You could try this