This outfit certainly would set you apart and ensure that that adcoms rememer who you are. However, I don't think Huggy Bear was quite the diversity that med schools are looking for. You could start a new trend. I'd do a purple suit and gators, but lose the hat and sunglasses (they're not ready for all of that yet). If someone says anything derogatory to you, just reply "hate the game, not the playa," and then pimp slap them, just to show 'em what time it is.
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.