Honestly... GO FOR IT!! That look is so in now and its funky as hell!!! C'mon sweetie you're from Montreal... Its all about style there, and when I look at that haircut I don't see old school skin head, I see the new, wicked look for an edgy girl, and darling I was there!!! No you won't need so much makeup! I've been seeing this style lately and it looks SICK and totally IN... Especially with big earrings... And lighter highlite panels!!!
You rock girl...