I now own most of the wardrobe I'll wear in Hawaii

Even though my Hawaii cruise is roughly 4-5 months away, I have gotten to thinking about the clothes I'll be bringing along on the trip.  

Although my trip is labeled as an 11 day cruisetour, there are only 10 days of scheduled activities - the first day is reserved for those people flying in from the mainland.  One could be 12+ hours in transit (like me) and arrive at the hotel in time for dinner.  And another person could be coming in from the West Coast, and arrive in time to spend a full day relaxing at the hotel.  I'll be out of touch for the better part of 12 days, as I lose a day in Eastbound transit due to the length of the flight and the time zone differences.

Since this trip will take place in the Winter, I have to carry a couple of outfits for mainland transit, as well as outfits for the 11 days in Hawaii.  I figure that I will wear something which I can remove layers from (or add layers to) while I am in transit. Of course, I have no intentions of wearing my coat while in Hawaii, but I must bring it along for my trip home.

Right now, I have 4 short, sleeveless dresses I've bought from Target, plus another from Lane Bryant.  I won't take all of them with me, as I will need a nice maxi dress fr more formal times.  But planning for this trip will force me to make decisions I don't want to make to keep things under control - such as limiting how much clothing I bring, so that my luggage falls within airline weight limits.

The way I see things, I'll need 3 pairs of shoes: the sneakers I'll wear onto the plane, "dressy" shoes (maybe a nice pair of flats) for "dressy" nights, and "water" shoes that I can use when going on a beach and walking poolside.  If I were traveling as Mario, I could make a pair of the shoes do double duty.  But, as most women know all too well, it requires more of an effort (and more clothing/accessories) to appear as a well put together woman.

Luckily, I still have time to plan my travel wardrobe.  But there will be other things that I have to plan for while traveling in female presentation - such as trimming my beard, and maintaining my made up face.  This will be a little bit more tricky....