Chase - Don't do it man. I see so much downside and so little up. The 'fashion statement' will be constantly misinterpreted -- if it is even a statement. See, it's happening already. Often with issues of fashion, people are looking for validation and discard opinions contrary to that which they are looking for. So, if you are truly looking for an opinion: don't do it and here is why: When I had long hair I loved the look -- in casual clothes, weekends after work etc. But, if I had to dress I just didn't like it -- I didn't feel like I was put together well -- I think highlights may do the same -- casually they may be great, for hanging out,dating etc. but, in the professional world there will be more occasion than not that you wish- well, lets just say, are hair hi lights the perfect accessory to your charcoal colored Joseph Aboud coat?