Surprisingly enough, everything laid out in this picture fits into my two packs in the upper right-hand corner (or can be attached to their exterior).

Clothing

The North Face 1/4 Zip Fleece Pullover (1)
Smartwool Baselayer (1)
PackTowl Towel (1)
T-Shirts (6)
EMS Lightweight Poloshirt (1)
Columbia Travel Button-down Shirts (2)
ExOfficio Boxer Briefs (5)
Smartwool & EMS Socks (6)
EMS Techwick Baselayer (1)
The North Face Better Than Naked Running Shorts (1)
Champion Gym Shorts (1)
Boardshorts (1)
EMS Convertible Pants (2)
Colorado Hat
Marmot Rain Pants (1)
Merrell Khaki Pants (1)
Jeans (1)
EMS Webbed Belts (2)
Merrell Hiking Shoes
Hoka Clifton 2 Running Shoes
Perry Top-sider Shoes

Odds & Ends

Fitness Gear 25 LBS Band
Apple MacBook Pro & Charging Cords
Journal (Maroon Cover)
Sea to Summit 13L Drybag
Sea to Summit 8L Drybag
Pacsafe 85L Exomesh
Toiletry Bag
Travel First Aid Kit
Travel Medications
Kindle Paperwhite
Bose Noise Cancelling In-Ear Headphones
Cocoon Travel Sheet (White)
Sawyer Squeeze Water Filtration System
Pocket Monkey Utility Wallet Tool
Spiraled Notebook (Black)
Bluefield Pack Cover
Speedo Goggles
GoPro Hero4 Silver & Accessories
SteriPEN Water Purifier
Philips Norelco Vacuum Beard Trimmer
Seagate 1 TB External Hard Drive
Polaroid Shutter Release
Canon G7X
Nikkor AF-S 55-200 VR II Lens
SD Cards (6)
Cable Lock
Padlocks (2)
REI M8+ World Travel Mate Universal Plug
Electronics Cords
Poweradd 10,000mAh Battery Charger
Hydroflask 32 oz. Water Bottle
MeFOTO BackPacker Tripod
Nikon D-3200 (Not Pictured)
Nikkor AF-S 18-55mm Lens (Not Pictured)
Packs

(L) Tortuga Travel Backpack – 44L
(R) 5.11 RUSH 12 Backpack – 24L