This photo was my set up in January 2009: 3 countries, 23 days: 4 undies, 2 socks, 5 shirts, 1 backpack.
I'm getting lighter and lighter each time I travel. The next time I take off will be around April 2010. I plan to travel for a few months while carrying a laptop for work and a bunch of photo gear for my personal pursuits. I've been doing some research and consideration of the clothes I'm going to take. I'll be mostly in hot climates.
I find my cotton t-shirts ruin after about 1 month of travel. Washing in the sink and wringing dry inside a towel destroys them in no time. Next time I'm only going to carry 3. I'll buy new ones as they ruin. Cotton is by far the nicest feeling fabric. Hangs nicely. But slow to dry and prone to wrinkles. Synthetic shirts dry faster but hang terribly on the body. Most travel or sport dry-fit shirts are horribly designed. Some synthetic blends will harbour sweat odours too, which is what they are not supposed to do. Why can't someone design travel gear that's actually stylish? Gstar? Diesel? Energie? Dsquared? Call me.
As far as undies go I'm going to go with 3; all merino wool. 1 one me, 1 on standby, and 1 drying from the last wash. That should cover it. I can't believe I used to bring 10+ pairs.
Next time 2 socks. All synthetic technical socks. They will dry/wash faster while doing a better job of managing moisture.
Pants: still can't find a versatile pair of pants that are light. Much like t-shirts, travel designed pants are horrible for style/fashion. I'm sticking with a pair of Diesel jeans. I'll keep them dry and clean. If needed I'll launder them at a hotel. Denim will take forever to dry if I hand wash them and I wouldn't want them to get smelly or start growing bacteria while drying.
Shorts: 1 pair of cargos and 1 swim trunk. Style wise, same problem as noted above. I'm sticking with a stylish pair made of heavy grade cotton. Travelling light doesn't mean you should look like a bum or a "backpacker". For the record, I'm a flashpacker :)
1 lightweight breathable jacket made by North Face. I've been caught in monsoons before. This will come in handy and will look much nicer than the bicycle sport-specific jacket I usually take. This new jacket looks nice zipped up too, can wear it to dinners and will also replace my heavy cotton hoodie.
Footwear: most crucial pieces. My feet do most of the work during travels so I've learned to never skimp on $$$ taking care of them. I'm going to invest in some ergo anatomically perfect sandals from Sole. Time to trash my Crocs (they served me well, wore them straight for 10 months!). I usually bring a pair of runners and loafers for nights out. I'm undecided about the runners for the next trip because I usually don't end up wearing them much. Next time I'll bring my custom orthotics as well.
That's pretty much it. I'll be using my 50L Asolo pack with a detachable day bag. The rest of the gear will be electronics and support equipment (cables, adapters, etc.). Electronics usually take up the most space and weight. They are a necessary evil though depending on what you intend to do for work while you are on the road.
March 10, 2011 update: Soles aren't the best or simple looking sandals. They were hard to find too. I decided to skip on them and ended up buying a simple looking pair of Crocs again. I bought them in May 2010 in Jakarta and they're working great.