When I first moved into hotels my luggage situation was a mess… as summed up in the picture below.
Over time I’ve realized that if you’re going to live out of suitcases full time you need to be super-minimalist and just live out of a carry-on. While it means my wardrobe is quite limited, it also saves me dozens of hours a year of waiting at baggage claim, not to mention the potential headache of lost bags (though amazingly enough even carry-ons can get lost).
Up until this year I had a Tumi 20″ Alpha International, as well as the Tumi Alpha laptop bag. It was a sleek set, if not a bit corporate looking. On US airlines you’re entitled to take aboard one carry-on and one “personal item,” so the 20″ rollaboard was my carry-on, and the laptop bag was my personal item.
But then I discovered the wonders of the weekender bag (mine is from Killspencer) . Yes, most people travel with a weekender bag as their carry-on. I, on the other hand, travel with my weekender bag as my personal item. And it has probably increased my carry-on capacity by about 50%.