You should rather decrease db of the rest (bass+mids) than increase treble to be completely safe as far as clipping is considered. As for digital EQing, I find it imperfecr as it introduce certain jitter, making SQ suffer (it makes music sound a bit blurred). You should also consider the fact that each headphone responds differently to EQing - some very well across the whole frequency spectrum, some not.
I would rather use analog-based EQing... But if you really need to EQ using your computer, pay attention to what kind of equalizer you use - I do very like Nugen SEQ1, PLParEQ, apQualizr and especially Brainworx digital v2. If you want something that's free, try EasyQ or Electri-Q.