The late columnist George Frazier posed that question years ago and the answer, he said, was "Look down." But in business and the professions, a man's shoes are just the starting point. When one successful man is sized up by another, it's because there's been a positive first impression that warrants a further look. Their eyes start at the face, go down to the feet and sweep back to the face. And everything they see should pass muster.
I'm generalizing today about the professional who travels a lot to meet other professionals in his work. The kind of guy who buys four to six suits a year and would be uncomfortable or worse if someone said he looked like a dandy. The man whose clothing is intended to convey a sense of accomplishment without attracting attention to itself, because the last thing business clothing should do is get in the way of a transaction with another person.
If a well dressed professional is wearing a suit, it will usually be a two button notch lapel model that, if it's not bespoke, has been made to measure by a maker like Zegna or Oxxford; conservative in cut and color, fitted, and made of obviously high quality materials. His cream, blue and blue striped shirts are also made to measure because that's the only way he can be sure to show a half inch of linen at his collar and cuffs. He's usually wearing a pair of polished oxfords, and his necktie is quiet - in fact, his boldest gesture is probably a quarter inch of white linen in his breast pocket.
The guy in the illustration above fit the bill when men were flying in propellor-driven planes, and would be every bit as good today if he left the hat at home.