Onboard a plane, everyone gets two items: a carry-on bag and a personal item. Here's how to get three bags for the road, without checking in anything extra.
Simply nest the smallest bag (usually, the purse or the daypack) inside the carry-on bag, so that its possible to pick the biggest personal item for packing. The small bag or purse is stowed away during transit, and doesn't count toward the two bag limit during transit. Because let's face it, no one is going to haul around a duffel bag for the day to day stuff.
This has worked well for us on super long trips where every possible inch was needed or where we had to haul around special equipment like camera and video gear. (Also typically has its own bag.)
For the last couple of trips, this has become our default packing method. This is great because it allows the passenger the full space of a carry on, the maximum usage of a large personal item like the Away Everywhere bag (which has the same capacity as a carry on lol), and a small bag for daily outings.
It's great if you're too cheap to pay for checked baggage, or hate waiting for bags at the carousel, while maximizing pretty much all the space available.
On one side of a suitcase, I'll pack the clothes—in packing cubes, of course—and on the other side, I'll lay down the purse on the other side. (Inside the purse, I'll pack anything else that doesn't fit elsewhere, like travel towels, hairdryer, makeup and other knickknacks. Think nesting Russian dolls!)
Once a traveler reaches the destination, all is left to unpack the purse, and put the proper contents inside.
This packing strategy tends to work a little bit better when the carry-on bag is a suitcase, but it really depends on the purse shape and the carry-on shape. 💼