The handkerchief, or pocket square as we know it today, was once strictly a utilitarian accessory, self-consciously carried in the hand so as to be at the ready whenever a man felt a case of the sniffles coming on. By the time of the early Renaissance, fanciful handkerchiefs became an essential accessory in the wardrobes of fashionable men who often tucked fancy squares of silk or linen into their sleeve. It was also an era when snuff was the stimulant of choice, thereby rendering the pocket square virtually essential lest one fall into the category quoted above.
The idea of “showing a little silk” carried on right up through the turn of the 20th Century, when it became fashionable for men to wear pocket squares in the chest pocket of their suits. Indeed, so pervasive was the penchant for pocket squares in the 30’s 40’s and 50’s that any man who left home without it looked as though he had neglected to finish dressing. The 60’s witnessed such fashion follies as the leisure suit and the Nehru jacket and pocket squares were, well, square, if not totally off the style agenda altogether.
Here in the modern era, pocket squares are once again in vogue. But to wear them properly it is advisable one not subscribe to the many and varied “folds” such as the “television fold,” “presidential fold” or the Cooper, Cagney, Astaire, et. al., ad nauseum so often recommended by misguided guides to dressing well.
Gary Cooper understood the "studied nonchalance" of a well placed pocket square
Best to just drape the center of the square over your index finger, grasp it at the puff or center, fold it up to meet the points and casually stuff it into your chest pocket with the puff and points showing about an inch above the pocket line. It should look as though you did it with your eyes closed, which you might actually consider doing. Once positioned, it should render a look of studied nonchalance.
Of course it may take some practice to get it imperfect. Ultimately, one’s pocket square, whether silk, cotton or linen, solid or patterned, should be worn with subtlety rather than showiness. The artfully dapper Jean Cocteau once sniffed: “Elegance ceases when it becomes noticeable.” Sound advice. And certainly nothing to sneeze at.