some or all of what you said is? Are people who have those things you said, someone you would want to introduce to a $50m investor?

Do I think someone that possess those characteristics could be successful, absoluteley, I know a few... but do I think they would be taken serious maintaining that look, no. Many wouldn't want to either. I know many individuals that have tatoos, but go to great extent to cover them up. Gigantic holes in the ears is a little harder to do, but the dreads can be cut.

But thats NYC, maybe in San Diego or Miami you could get away with it more easily.

But the ultimate issue about dress, is really on one thing...

What will your investors think of how you look. You dress mainly to get your investors money, nothing else. Sometime you can find investors who will enjoy the outlier character from what you see in a firm, but mostly they want nice, clean cut, tight hair, "polished shoes" type guys investing for them.