I love beautiful hair that looks slightly undone and not too perfect. The best looking hair, in my opinion, is the morning after hair. Not trying too hard to compete for attention and never overwhelming the person. Like the owner did their hair last night before going out and forgot the brush it in the morning after sleeping in. Hair as almost an after-thought. Haircut that is not a haircut. Overly coiffed hair often just reminds me of soap actresses or hollywood award shows.
One of my favourite looks is long, ever so disheveled hair on a girl wearing a masculine suit – perfect balance of feminine and masculine aesthetic. Something like a redhead in a grey flannel suit.