Silk Dress - I don't remember which combination of "soft/smooth shiny/shimmers" you need for silk, but you need silk.
Diamond Tiara- Talk to the guy with the shop on the north end of the main town, spend a night at the inn, buy the most expensive thing.
Blonde Wig- Win the Squats competition.
Bikini Briefs- Go to the 'Group Room' in the honeybee inn. (Fat guy outside the Inn area has the members card)
Makeup - AFTER visiting the room in the honeybee, go to the Honeybees' dressing room. One will give you makeup.
Ummm... If you have the sexy cologne, I think that's it.