(usually several years behind the current fashions)
As one who has never had a suit “tailor made” there are some things in life I didn’t find out about in due course during my education as a younger man.
How do you dress? (you mean like dressing a deer?)
I was probably in my early thirties before I heard that specific question and only then when a co-worker was relaying his experience of having a suit made and how the tailor had to explain what it meant.
How do you dress? (underwear first, then socks, pants, shoes, shirt etc.)
I’m guessing there have been government and private funded studies trying to understand the answer to the question. Probably ranks up there with the blue/red state and boxer/brief debates. Inquiring minds want to know.
How do you dress? (as comfortably as possible)
As a “virtual office” at home most of the time worker, my attire is basically the opposite from ‘dress-for-success’. I may never have to buy another suit again which pretty much guarantees I will never hear the question asked in its proper setting.
So, how do you dress? (who do you think you are, my tailor?)