I've traveled for a living for over 30 years and if there is one thing I've learned about packing for travel is that you can travel anywhere anytime with a simple set of rules. First, do it the same way every time. Second, you do not need more than three days of clothes no matter where you are going or what you are doing. And, Third, the most important rule, never pack in the dark! (If you have ever had to give a brief to an important customer wearing a blue suit coat and a brown pair of suit pants you would understand why this last caution is the most important.)
For almost 20 years as a pilot for North West Airlines, now consumed by Delta, I had two, and only two, plans for packing for all my travel. My Summer plan has always been:
I wear:
Blue blazer
Blue Jeans or slacks (Slacks only if I have to go directly to a meeting off the flight.)
Button down shirt
The running shoes with the jeans or the dress shoes with the slacks
I carry:
Extra Padded Brenthaven computer briefcase
I pack into a "Pretty Neat Executive 22 Pilot Bag:"
A "Dop Kit"
A pair of flip flops,
Light weight running shoes, (I like New Balance 888's)
Slim, light weight dress shoes (Definitely not Brogues [Look it up, Punk!])
Nylon bathing suit, (So it dries fast)
Pair of light gym shorts nylon or polyester (So it dries fast)
Pair of jeans
Pair of shorts
Four pair of U-Trou, (Boxers and only Boxers!)
Two dress socks for the suit
Two dress socks for the slacks
Three pair white socks,
Three t-shirts,
Three casual shirts,
Three dress shirts,
Thin nylon wind breaker
Thin pullover collared sweater
Umbrella
And in a hanging bag:
Suit (Preferably Kaki)
Gray or Kaki slacks
Belts and ties
For the winter, I dump the:
Flip flops
Trade the light weight running shoes in on a more solid pair
The shorts
I add either:
Down Parka (Denver, Anchorage)
Leather Jacket (Chicago)
Overcoat (New York)
Depending upon the circumstances
Unless you are going to a unique and unusual situation where laundry and dry-cleaning are not available or the nature of your travels are unusual, the above plan will stand you in good stead for almost anything. However if you are going river rafting, participating in Burning Man, visiting certain parts of Thailand, Scotland or Botswana, or going to a Windmill Greasing, you may want to tailor your packing for the specific itinerary or event.
