Depends. If your gonna do that then spend thousands of dollars on designer cloths then no. I do have a thing for scene/emo girls with "weird" hair colors. Familiar with Hayley Williams (my only celebrity crush by the way)? Lead singer of Paramore? She has red hair sometimes. Sometimes orange. It goes well for her and I think it looks good.
As far as a previous poster said about clean cut guys not liking it? I'm as clean cut as they come (ex military... ect) and I like it.
Short answer... If your the girl next door... don't do it stay your natural color. If your more of an artistic abstract kinda person then yah go for it.
It can be very drastic, depending on your current color and skin tone.
I have dark features and I dyed the tips of my hair red. It looked pretty cool (when it was tied up the end of the pony tail was bright red) I got a lot of compliments. It was just the right amount of color and it was easy to get rid of. I just got a hair cut and there it went. No trying to match the shade of my natural color and it didn't do any damage to my hair either.
i think clean cut type guys don't like it as much, but guys in certain subcultures would