The last time I wore pleats, they only came in plaid and were paired with knee socks and deck shoes.
Now I have no less than four pleated skirts, a big adjustment for an over 40 pencil skirt girl.
After a considerable amount of trial marked heavily by error, this seems to be the way to go - at the knee, shirt tucked, skinny belt/waist of some sort and a sharp eye for subway vents with big gusts of air.
For the more daring/young/skinny, there is the longer pleated skirt (but still moderated with the tucked top and skinny belt.)
The long bulky top over long pleated skirt can be pulled off by only one woman in the world, and she's in this picture. So don't bother trying it.
Are you wearing pleats? What's working for you?
Images: Via Love Maegan; Elle via Say Yes to Hoboken; Lookbook.nu; We Heart It; What I Wore; Asos; Style It Lovely; Like Whatever Online; They All Hate Us.