Packing light. (realizing that I cant take 20 pairs of shoes on a boat)

15 days till I board the plane for Annapolis MD. I have started making a list. As I write, I try to put things on the list that are necessities, which proves to be a challenge... The list starts like this:

Foul Weather Gear
Deck Shoes
Dry Bag
Flashlight
Rigging Knife
Hooded sweatshirt
Sweatpants
Camouflaged Red Sox hat
White Red Sox Hat
7 pair shorts
7 shirts
2 bathing suits
board shorts
pair of "dirty boat work" shorts
undergarments
Liberty Jacket (cant go sailing without it!)
gold havaianas
blue havaianas
yellow and brown dress (in case i have to go out in savannah)
Brown pumps (to match the brown and yellow dress)
make up
curling iron
blow dryer
shampoo/conditioner
soap
Leather bound journal
pens
cell phone
cell phone charger
polarized sunglasses
sunscreen
toothbrush toothpaste razors
contacts
blanket
pillow
hairbrush
hair ties

I know I'm forgetting something... Yall help me out!

In the pic above: a glimpse of the brown and yellow dress I can't leave home without.