To wear a bra, go to the clothes store called Modo, and walk up to the cashier. It must be a female cashier for this trick to work. Knife the cashier, and stand over her body for one game hour. Travel back to Roman's apartment, and go to the wardrobe. You should now have an option to wear a bra. Wearing the bra will change NPC dialogue, and they will start saying things to you like "What the hell are you wearing man?!"