I'm a recent convert to the layered bag idea for flying as well. I'd also recommend a Longchamps, with a cross body inside. I love that you don't have to worry about them at all, as they can be wiped clean. I have a fake Longchamps that is probably equivalent to an XL, which is great when you have a longer flight, so may need more with you, or want a change of clothes. On shorter flights, a large one is fine.

I almost always check a bag, unless I’m only going for a day or two. I hate worrying about whether I’m going to be able to get space in the overhead and all that maneuvering makes boarding take forever. I usually put a purse or two in my checked bag and put my wallet stuff in a tote for the journey.

I have a system. It works for me. As with everything else, YMMV. I have been everything from a road warrior to a 3-4 trip per year person over the last 20 years.

My rolling carryon is a 10(?) year old Briggs and Riley. Can't live without it. One big open section, also has a folding garment section on the top of the lid. Best part is there's a zipper between the outside mounted metal handle structure and my havianas flip flops fit perfectly in there. Been doing that for years! It also (key thing to note!) has a system where you can attach other bags to it.
My "personal item" is a bit of a game, like you mentioned. For years now I've used a swiss army backpack (from Sam's Club, I think?) which is carefully loaded. It has the TSA approved zipper section for the laptop which I use. Then the big section in the middle carries my makeup and jewelry at the bottom (in cases), leaving just enough room to slip my cross body purse in there for boarding only.
The front section of the backpack carries all my cables and cords (techie here!) as well as my TSA liquids bag (for easy access bc here they ask you to take it out in the security screening area).
When they start pre-boarding, I stash my purse inside the backpack, attach the backpack to the rolling carry on, and board. In the jetway I pull out the purse and put it back on, leaving the backpack small enough that it will fit under the seat in front of me. To date, no one has ever questioned me about this. The check seems to be at the boarding gate.

This would NOT work for weight-based carry ons (I've heard this is common in Europe and outside the USA), bc my system is heavy!!! But I really never carry any of the items on my person (other than the cross body purse).
THis B&R rolling carry on even with the backpack attached is so easy to maneuver, I can guide it with one finger. FOR ME, having the wheeled carryon is worth it bc it makes it so much easier to attach everything to it and easily roll through the airport.
Good luck!

ETA: my approach is one to maximize what I carry onto the plane ...

FWIW, Longchamps has come out with a cross body version called the Neo. The two handles are shorter, so don't go over the shoulder like the LePliage, however that is what the strap is for. The Neo was my main commuter bag for the last 3 years I worked since I could pack all my junk into it (including packed lunch box), it was light, and it was waterproof.

And.....my suitcase is branded by an air carrier and a smaller European size, so rolls down aisles without catching and fits overhead easily. During a crowded flight I once actually got it under the seat in front!

Didn't read the other responses but I'll repeat my own strategy that works great for me.

I have a nearly 5 year old Briggs Reilly tote that has a sleeve that slips over my roller bag. It's nylon and really simple, rectangular shape, with a padded section for laptop (would fit a much bigger bulkier laptop than my 13 in mac), inner compartments for headphones, pens, kleenex, glasses, and other smaller stuff, big center compartment for bulky items like scarf, cardigan, book, even a coat folded up, and a pair of shoes, a water bottle... and yes, a small cross body bag that tucks away for the security line. It all zips closed so nothing falls out as it goes through the scanners. The zipper has never failed, even when I pack it over full. It also has large outer zip pocket which I use to stash receipts and papers and other things.

This tote fits a lot and is lightweight. It is not fashionable, but oh so functional!

A backpack that I shove my purse into plus a small carry-on that will fit under the seat in front. I want everything available so do not use overhead bins. ( need meds, protein bars, water bottle, iPad in route. For some reason, the airline personnel do not notice a backpack on your back as much as a tote bag and have never questioned my personal item.

A subject near and dear to my heart.

If I’m going to be doing any serious photography on a trip, I’m guaranteed to check a bag because my camera bag already comprises one carry-on (I would never check camera gear!).

My preferred “personal item” carry-on is a Briggs & Riley tote that sounds just like Shiny’s. It fits my laptop in a neoprene sleeve plus all my other necessities. But it’s not easy on my shoulder when I have to carry it without a rolling bag.

On this trip we are currently on, I decided to bring a backpack instead. I don’t bring a laptop, and I thought the backpack would do double duty as a day pack for light hiking and knocking around town. So far it’s worked out well. It held my stuff every day when we went out on safari game drives and did the job beautifully. The floral pattern even does a great job of hiding dust and dirt!

So clearly I am a fickle carry-on item fan. I have a big straw bag with a zipper close (zip closures are a MUST) that goes on beach vacations with me. I like having different options for different types of travel since I do such a variety.

Hey Janet, can you show me a pic of your B&R tote? I'm looking to change my 2nd carry on and that may work. Also, I am with you on the fact that it MUST zip. It would drive me bonkers to not have a fully closed item on a plane.

I use a lePliage and have a tote organizer insert thingy (I think you can get them on Amazon, to organize my wallet, phone, etc.

I also have a small Briggs & Riley to go with the larger wheeled ones, but it's just way too heavy on it's own, esp. without wheels. That led me (along with this discussion to remind me) to try out a new one. I just got it and it looks like a keeper!

Comes with a large tote bag too. I might be able to travel with just these two items.

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Mr suntiger and i both bring laptops when we travel, since he travels for school and i write, so we use this rolling multi compartment bag (now using it for work). Then just a regular small purse aside from that.

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Another frequent traveler here. My system changes depending on destination and work vs play.

Suitcase - always carryon. I have 2 sizes of Briggs and Riley suitcases and they not only last, but customer service is outstanding (a broken zipper on an 8-yo bag resulted in a brand new replacement!)

Personal item - if long trip and work - Lo and sons OMG. Looks like a bowling bag, fits anywhere and holds everything. I’ll throw in a wristlet or clutch for dinner or non-work outings,

Personal item - if short trip and work - Le Pliage or KS tote. Essentially I skip a separate purse and just use the tote.

Personal item - long trip and fun - backpack or Le Pliage tote, with a small crossbody in the carryon to use on sightseeing days

Personal item - short trip and fun - tote or smaller purse. Must hold an iPad, but nothing larger.

My other important rule - clean out bag before and after the trip. It’s amazing how much stuff gets added in and adds weight!

ABC, my B&R tote kind of looks like this --


This must be the updated version, as mine is a bit different, but this is VERY close.