I used to travel a lot for work. I’d only use 1 bag. Last trip was in October, 9 days in Asia – Thailand and Singapore for both work and play. Took 1 soft carry on bag including laptop, ipad, kindle, swimming stuff
I put all my shirts, ties and trousers in an Eagle Creek shirt carrier – http://shop.eaglecreek.com/packit-folders/l/211
I can get 5 shirts in there, two pairs of trousers and some ties if needed. Jacket is either folded gently and placed on top, or worn for the flight
I’ve used both the special jacket folding method (one shoulder inside out and placed into the other) and the normal just fold it up approach, had no difference in results
I also used two packing cubes as they let you get things in the bag in an organised and simple way. Only one pair of shoes in hand luggage, one worn and maybe flip flops if needed in the bag. Shoes also have stuff in there like travel charger or belt
My toiletry kit is tiny and fits into one of the ziploc bags making security a lot easier
My bag is a Lowe Alpine TT Carry on 40