Men’s dress clothes have pockets, don’t they?
Men’s dress clothes are supposed to look good on the men, aren’t they? I have certainly seen men wearing dress clothes who I thought looked very good in them.
Why are clothes with pockets considered to flatter men, and not women?
To be fair, it has always been considered a bit infra dig for a truly well-tailored gentleman to actually use the pockets in his clothing to any detectable extent. A very slim billfold and a key is about the limit of what a man can put in a really nice suit pocket without ruining the line.
Clothes with more wearing ease can accommodate somewhat more well-filled pockets without looking awkward, of course, but that’s as true for women as for men. However, women’s “stylish” clothes are expected to be more form-fitting (less wearing ease) than men’s. I don’t think anybody here needs an explanation of why conventional standards for “stylish and attractive” clothing for women emphasize showing the contours of the figure more than similar clothes for men do.
Wonderfully explained! 
Right — I can have a tailor cut my suits to a look that is not tight to the body, and if he does it right, people will just say “oh he’s into classic style”.