I'm currently sitting on the floor at the airport here in North Carolina, I hope to eventually board a tiny aircraft and get home one day. The flight out reminded me why I have given up on even the good old "roll-on" cart which no longer fits under seats or in overhead bins - as the folks coming down learned.

For me, the extra hour of travel time spent checking and retrieving bags is simply not worth it, more often than not I arrive late anyway, so I don't have more time to waste on baggage claim, and on the way home, I really don't need any more time in the airport.

Still, I'm expected to be able to make presentations, check email and all that on the road.

I've converted from a rolling cart to a Scott E-Vest, which I pack with not only toiletries and various electronics, but also my neat little ASUS eeePC, a Blackberry Curve and some small cables. Also in the vest is an EMPTY stainless flask - I fill it up after the security gate, and some snack items.

In a small bag, that a less many person would call a "largeish purse" I pack a shirt, underwear, a few bits of paper, inflatable pillow an umbrella and a few other items. That's it.

If I need anything bigger, I overnight it to my destination. I whiz through the airports now!

I've found the standard luggage combination of a small briefcase type bag and a small bag for clothes to be the most versatile for a variety of trip lengths. A little more bulky then what you're carrying but depending on the level you have to make your presentations at, potentially very worth it. I've never quite understood why the briefcase went out of style, but for a businessman it is a more then acceptable way around the man purse stigma.

Depending on what your required level of attire is when you land, you might consider the Sky Roll for your clothing bag. My dad has one and he loves it. It has a rigid inside compartment with a garment bag wrapped around it. Rolling the garment bag keeps suits and other clothing from wrinkling while making the garment bag infinitely more managable. The main compartment opens on the end so you can get to it with out removing the garment bag. The whole thing is just the right size for an over head bin.

I agree... Though when I travel, if its going to be an under 3 day trip, a simple oakly backpack serves me well - fit into the college kid look (at least I wish I do).

I put what I need into it:
-extra pair of dockers
-two extra shirts pressed and folded professional
-undies and socks
-smallish laptop - in sleeve (can carry on its own once to destination w/ room for necessary powerbrick)
-associated cables
-book
-mobile
-ipod nano

This is my basic travel kit... and if i need to stay longer, then I become very friendly with a local dry cleaner.

I don't mess with bringing the shampoo's, toothpaste, etc... especially if coming into states. I just get that at the hotel or drug store on the way.

Put the pack over one shoulder, pretty light in itself (by comparison to my contracting days), and just walk. Things on wheels have a way of breaking at the wrong times, especially in airports.

Awesome resource for traveling light:

http://www.onebag.com/