(I know this is stupid, but ...)

I'm trying to think of somebody cool & stylish who's clothes really 'fitted' them.
Help me out?
The man who's clothes fitted him best that I can think of is Cecil Beaton. This is because he often wore RTW in a size down from his own... (True story!)
And how did Cecil look?
.. Well, not brilliant...
A bit funny really...

In bespoke & MTM I look a bit of a clothes horse. Put me in RTW with a few tailored alterations and I look much better for a fraction of the price. WTF?
I'm happy for you to tell me that that's just me & my own eye for these things, but my point is that the OVERLY tailored look is a damn odd look. Not quite right somehow.
To quote Chris H. : " Get the fit right around the shoulders" (OK, those weren't his actual words, but they come very close). And I think Mr C. was bang on the money - all the rest can be altered, or not (even), it's up to you.
Tailoring can become such a fetish that you can end up worrying about 1/16th of an inch and end up looking... well, ... certainly well tailored, ... but not really very well dressed.  Am I alone in thinking this?

Miles.