I’ve given quite a bit of thought to the stuff I carry with me when I travel. I try to travel light, remain comfortable, and be prepared for unexpected issues. Packing things in smaller bags allows me to stay organized and allows the packing process to be very logical for me. Items like the merino t-shirts or ExOfficio boxers are more expensive than other versions of the same clothing items but allow me to wear them several times without washing (and without smelling). Should I have to I can quickly wash those things in a sink and by morning they will be dry. I also try to buy quality when I can making me have to replace items far less frequently. An additional benefit of going for quality items is that manufactures like Leatherman, Icebreaker, or Ibex have awesome warranties and great customer service.

Pockets: Details Here

Parker Jotter Stainless Steel
Leatherman Skeletool (Left behind when flying)
ThruNite T10S Stainless Steel Flashlight
Apple iPhone 5s 32GB (Space Gray) in a OtterBox Commuter Case
Coach Slim Wallet with Money Clip

Wrist:

Pebble Steel Smart Watch (Brushed Stainless) [Right]
Titanium KIA Bracelet [Left]

Clothes:

Outer Layer: Kenneth Cole Single Breasted Raincoat
Added Warmth: Patagonia Nano Puff Jacket
Button Down: Icebreaker Seeker Long Sleeve Shirt
T-Shirt: Merino V-neck or Crew Neck by Minus33 or Ibex
Underwear: ExOfficio Men’s Boxer Brief
Socks: Chrome Merino Crew Socks
Pants: Levi’s 505s (Rigid) or Levi’s 505s Twill (Graphite)
Boots: Wingtip Boots or Corcoran Jump Boots (I got mine on a steal through eBay)

Backpack: Minaal Travel Backpack

Travel Electronics Kit: Contained in Eagle Creek Travel Gear Pack-It Sac, Black, Small

Belkin Lighting to USB 4′ Cable
HDMI Cable
Extra Ear Buds
USB Drive
Car USB Charger
Square Card Reader
Pebble Steel Charging Cable

 Travel Toiletries Kit: Contained in Eagle Creek Travel Gear Pack-It Sac, Black, Small

GoToob 3 Oz Travel Bottle filled with Dr. Bronner’s Liquid Soap, Tea Tree
Exfoliating Scrub
Razor
Somersets Shaving Oil
Old Spice Deodorant
Cotton Swabs
Travel Tooth Brush
Tooth Paste

 Clothing: Contained in Eagle Creek Pack-It Cube

ExOfficio Men’s Boxer Brief (1-2 pairs)
Chrome Merino Crew Socks (1-2 pairs)
Extra Pair of Pants Levi’s 505s (Rigid) or Levi’s 505s Twill (Graphite)
Extra Merino T-shirt
Sweater

Misc:

Vapur Eclipse Water Bottle, 1-Liter
Clif Bars
Travel CPAP Machine

 Presentation Kit: Contained in InFocus Projector Case

InFocus LP 70+
HDMI Cable
Keyspan Presentation Remote
Powered Speakers
Three Plug 10′ Extension Cord
Details and pictures here.

Messenger Bag: Tenba Large Messenger (My model is older but this one is pretty close)

MacBook Pro 13″
iPad Air 1st Gen. 16gb in an Invellop Black Leather Case
Steno Pad in a Leather Case
Western Digital 1TB
External Drive

Sony Earbuds
Belkin Lighting to USB 4′ Cable
Small Trauma Kit

Details and pictures here