Two recent flights I had were flagrant examples of this type of pax...even the FA's were commenting about the kind/quantity of luggage being brought on. One woman literally had a huge black plastic trash bag for her luggage...no doubt her luggage had broken, but it was overflowing (think large yard cleanup bag) and torn!! Unbelievable. Try downsizing what you take with you...obviously if you're wearing 3 piece suits, you're probably not trying to do carryon; but maybe you could trim it down and get a laptop case that will hold a few small extras (mine even has rollers and a pull handle hidden away) and fits perfectly under the seat. The weekender just seems over the top ... you'll probably get by with it, but if I were on the flight I'd hope you got it under the seat and not try to put 2 items in the overhead. Gee...November air traffic, holiday travelers, and everybody wants to take all their stuff with them on the plane....that will be soooo fun.