Hi..and a massive welcome to the number 1 site for frags.....
Don't look too deep into things.. wear what you want.. when you want! A good spraying method that works for me is to hit the stomach, chest, inner elbows (forget the wrists as the scent just rubs off whenever you make contact with anything) behind the knees and one shot to the back of the neck for sillage. Also.. give one spray to your shirt from a distance so as not to stain the garment.. The reason for spraying under your clothes is this.. the clothes help to trap the scent in and when your body heats up.. wafts of glorious sillage will be introduced to your nose
WAIT 10 mins.. then spray over all the same areas (as above) again. This gives you a double layer and fantasic longevity! Make sure you do all this at least 90 mins before you are due to leave the house.. by then.. the scent will have been on your skin long enough to hit complete drydown and smell at its best!
A good rule of thumb is this..Heavy scents such as Pi for night/winter.. light scents such as Acqua Di Gio for day/summer.. like I've said before..anything goes..A heavy Oriental such as Pi if sprayed very lightly can work in the day.