At this point in life, after experiencing a few baggy moments that left me with too much loose cloth and a few tight choices that ripped and tore at seams to hastily sewn, I would measure my philosophy moderately.
I would choose a fabric that is going to wear well over time, in all ethical climates, and for many if not all occasions. I would avoid a cloth that called too much attention, either by its ostentatious luxury or its coarse cheapness. I would make my selection based on its reputation for quality and durability, even if these characteristics were recognized only by a knowing few.
I would choose a tailor whose clients not only dressed well but behaved well, as if to confer a wardrobe’s place as a part of a man, not the whole of him.
I would have only a few personal preferences in the cut and style, as a tailor has studied fabric and cut and body and fit for years, and should know his business well. I would be thoughtful during the fitting process, ask questions, listen, and make few demands.
I would choose a style that looked best on me and worked best for me as I went about my daily life. I would avoid fashion, eschew trends, and hold fast to tradition, perhaps with a personal twist. My suit should fit well, but it should have room to move, have extra fabric or mechanisms that, as time passed and I changed, I could make tasteful almost invisible alterations. The last thing I would want to do is discard a suit because it no longer fit: I would know that I had not made a good choice, or that I had changed too much and had strayed off my path.
Once my suit was complete, I would wear it with a certain regard: it had taken time to make choices, time to construct. It had been a creation of partnership between my tailor and me. I would also wear it with a certain disregard: a suit’s function is to be worn, to serve a purpose, to be lived in, to be our armor as we go forth and conduct the business of life.
To the extent that it performs this function in comfort, durability, and yes, some style, is the extent of its value. So indeed, I would take care in this endeavor.