My hair is black on the sides and back of my head (my natural color), and bleached a golden/caramel type of blonde on top. The sides are shaved and the top grows down to my shoulder. I am a male.
Will my hairstyle affect me at all when applying to medical school, or when applying for jobs after medical school?
Yes. It will be perceived negatively.
Medicine is inherently a very conservative profession. Your dress and grooming are expected to conform to professional norms.
Remember you will be a in profession where you you will be dealing with the public at all times, and that many of your patients will be older individuals.