The present invention is generally directed to dermatological devices and methods in which one or more skin characteristics, such as the melanin index, are determined by analyzing radiation backscattered from a skin region illuminated by at least one, and preferably, two or more wavelengths, e.g., in a range of about 600 nm to about 900 nm. In many embodiments, the radiation is coupled to the skin via a waveguide, and an optical sensor is employed to ascertain contact between the waveguide (e.g., a waveguide surface adapted for contact with the skin) and the skin.