When my travel involves work, I wear whatever jacket/blazer I plan to wear for meetings with skinnies, a t-shirt, scarf, and either low-heeled oxfords/loafers or my 20-hole Docs (in winter weather). If it's not for work, it depends on season. Colder temps usually mean just switching out the jacket for a sweater. Warmer temps might mean a dress with sandals or flats.
Phone, wallet, iPad, bluetooth keyboard, small notebook, pens, bag of cashews, lip balm, hat/gloves (winter), and sunglasses go in whatever bag I've chosen for the trip. All clothes are packed in one of my Timbuk2 Wingmans -- the small if the trip is less than 6 days, the medium if it's up to two weeks -- and taken as carry on. I like to pack lightly, and this is the system that's become most efficient for me over the past few years.
If my travel is yoga-related, I switch out the purse for a Lululemon Carry Me Om tote, because I can slide my yoga mat into the back of it. Clothes still go in one of my Wingman bags.
(It's possible I've spent too much time refining my travel strategies over the years. Hah!)