It's been a while since I traveled for work regularly. But when I did, I invested in a TravelPro wheel-aboard bag. Those things wear like iron, but they look like everything else: black cordura, blah-blah-blah.
I'll be breaking out the bag soon for an upcoming trip, with three days of business casualwear in that single bag, with laptop on the side. It'll be an exercise in squishtastic packing, but I think I can do it.
Check a bag? Pfft. No.
Not after sitting for two days of a three-day conference beside a bevvy of belles whose luggage took a trip to chillier climes (Chicago) while they cooled their heels in Atlanta, trying to make jeans and jogging suits look quasi-professional with the help of the jewelry they'd stowed in their carry-ons.
Lesson learned: pack light and take your luggage on board. And if you can't, make sure the outfit you're wearing on the flight is comfortable while minimally passing as professional.
Admittedly, I wear way too many pairs of shoes when away -- out of necessity. Plus, I normally schlep along a serious hair dryer whenever I travel because hotel models are seldom adequate. Oh, and did I mention my obsession with hair products?
This is going to take a while.