Huggy Bear had three things going for him in a med school application 1) minority background 2) poor background 3) paid and volunteering experience among drug addicts that inspired him to further investigate the human psyche. I can probably write a winning AMCAS application essay for Huggy Bear.
As for the outfit, I am sorry to say that it only fits the med school criterion of diversity if it's ethnically oriented (except if you are Polish, Russian, Croatian, all Asians, Iranian, Iraqi, Libyan, Palestinian, Egyptian, Somalian, Sudanese, etc). Also, since many pimps are white, pimps do not belong to the historically disadvantaged groups.