Breastfeeding question...?

my son quit breastfeeding so im in the process of drying up... they are finally starting to soften a little. the dr told me to wear a tight sports bra which i have but at night i take it off cuz i cnt sleep with it on. but then i leak... my question is when i leak does my body think that it needs to make more milk? should i wear the bra so i dont leak or does it matter?