Can you look stylish wearing ill-fitting clothes? Some people seem to be able to carry it off - a lucky few seem to be able to look good wrapped in old sacking.
It's all to do with how you hold yourself. If you look confident and stand tall your clothes take a on a status which is secondary to you. This is how it should be - you should make clothes look smart, not vice versa. This may sound nonsense, but people who dress well can do so without having to wear expensive beautifully-tailored clothes. Size and height have little to do with this. It's a natural elegance which shines through. I think that this elegance can be learned with self-confidence and through experimenting with your style - find clothes you feel comfortable in.
Having said that, for the majority of us, wearing well-cut and good-fitting clothes is still the safer option if elegance and style are the aim.
As usual, I go to the Sartorialist for evidence. In all these pictures the people are wearing clothes which do not fit well, are too baggy, or just not nice. Yet, somehow, the subject looks comfortable and elegant and is noticed for good taste or style, rather than because he looks a mess or a little silly.
See also my previous post Cool and Rumpled. All photographs courtesy of The Sartorialist.