[trip style = packing light]
Do you want to become someone who - casually saunters on the plane avec purse and stylish carry-on - walks off the plane and by-passes the luggage area - heads right to the cab/car area - is sipping a mojito poolside within 1-hour of landing
Although travelling solely with a carry-on is can be challenging given the space challenges, adapting is possible! With a little forward thinking, carry-on travel can be learned!
Case in Point Although this is an extreme example, my husband travelled to China for one month with a carry-on sized suitcase and a small backpack. The size of his bags did not limit him--it seemed he wore different outfits all the time. He might be mad if he knew I said he wore outfits... A less extreme example is when we only took carry-ons with us to sip wines in Napa. I was pleasantly surprised when we were able to stylishly and efficiently pack for 6 full days. Bonus of staying at a nice hotel, they gave us the items we weren't able to bring at the time: razors, tweezers, extra toothpaste, etc...
Packing light - documents (including passport) - book/mags - ipod - phone - pashmina - attire geared at your destination's weather (check the weather report before you leave) - minimal shoes - mini toiletries (toothpaste/brush, deodorant, comb, hair stuff, face wash, meds, make-up) * your hotel should be able to provide: shampoos, soaps, hair dryer, cotton balls, q-tips, toothpaste, razors, slippers, etc...
Strategies Pashmina/big scarf - wear it as a blanket on the on the plane, as a scarf and as a Grecian-style bathing suit cover-up.
Go monochromatic - choose a colour-theme for your outfits, then only bring pants/tops/skirts/jackets that match each other. Same goes for shoes.
Semi-packed and ready to go - keep the items that you like to travel with in your carry-on at all times, that way, when you leave for your next trip, you'll have most items ready to go.
Get organized - make lists for the items you'd need for a weekend trip, tropical getaway etc... half the time we spend packing is just DECIDING what to wear. This will also help if you decide to take a spontaneous trip!
Choose clothes that will 'double in the program' - if space is at a minimum (and I assume it is) bring clothing that will play double duty, like a top you can wear to the pool (as bathing suit cover-up)or with jeans, or shoes that can go from day to night.
Pack an extra bag - consider packing a flat, easily-foldable bag (like a longchamp handbag/le pliage) that can be used a) as a make-shift pool or beach bag, b) as a large purse, or c) as an overflow bag should the malls get the best of you.