Entering the uninhibited lifestyle as a single man is a completely different game than arriving with a partner. The velvet rope is often pulled a little tighter, and the expectations for your behavior, style, and etiquette are exceptionally high.

Packing for a traditional luxury vacation is relatively straightforward: resort casual for the day, elegant resort evening wear for dinner.

​But packing for a lifestyle-friendly getaway? That is an entirely different art form. When your itinerary includes topless-optional beach clubs, sultry playroom nights, and elaborate, uninhibited theme parties, the standard packing list goes out the window.