In terms of luggage, I am bringing a large rolling duffle bag, a ~49 liter hiking backpack, an L.L. Bean rucksack, and a duffle bag from my high school soccer team.
Pre-Departure List:
Clothing:
Wool Blend Socks x 7
Regular Socks x 20
Khakis x 3
Black Slacks x 1
Quick Dry Convertible Pants x 3
Blazer (for formal occasions)
Short Sleeve Button Downs (Quick Dry x 2, Regular x 3)
Long Sleeve Button Downs (Formal x 5, other x 4)
Polos x 4
Athletic Shorts x 3 (gym shorts, running shorts, soccer shorts)
Nice Shorts x 1
Underwear x 28
Marmot PreCip Rain Jacket
Fleece Jacket
Sweater x 3
Bowtie x 2
Tie x 2
Shoes:
Black Dress Shoes
Merrell Hiking Boots
Asics Running Shoes
Teva Ombres
Flip-Flops
Sneakers
Other:
15 Puzzle
Plastic Playing Cards
Books (Watership Down, Book of Knots)
Journals x2
Pens/Pencils x a lot
Notebooks (& extra paper) x3
Watch x2 (GPS, regular)
Water bottle x4
Ab Wheel
Jump Rope
Coleman Sleeping Bag
Leatherman Multi-Tool
Black Diamond Spot Head Lamp
Back Pack Rain Cover
Toiletries:
Deodorant x4
Razor + Extra Razor Blades
Toothbrush x4
Dental Floss x2
Allergy Meds (90 day supply)
Technology:
Laptop (2014 MacBook Air) + Charger
Seagate External Hard Drive
iPod Touch
Kindle Paperwhite
Water Proof Panasonic Digital Camera, Charger, 2 batteries
GPS Watch
Food:
Jar of Jif Peanut Butter
Candy (Easter Bunny, Skittles, Swedish Fish, etc)
Nature Valley Bars
Luggage:

Changes/suggestions (to be added in a few months):
No winter jacket yet, just in case I wouldn’t need it.