I would love to stay stylish when traveling, but any trip over 3 days gets inordinately inconvenient with a heavy, nice-looking traditional bag. This is exacerbated by the fact that as a SFer, I almost always take an extra pair of shoes. If there were a practical way to do it I would love to carry a SAB gladstone style, but it would weigh a ton fully laden. I no longer see the logic in justifying the extra weight.
I had been using an 11 lb kirkland rolling bag (22") for years, I got tired of how heavy it was and how little capacity it actually had, even though it was extremely well made. And half the time it gets "side-checked" when flying on the smaller planes, causing delays. I don't use it now except for car trips.
These days I have been convinced to use convertible backpacks. They are basically like carrying a 22" roller bag on your back, but minus the 8 lbs or so wasted on the rolling hardware.
However, I might be convinced by the newer generation of superlightweight rollers, for example this weighs 5 lbs: