Many months ago I posted asking for carry on help from frequent flyers. I got a ton of great advice and settled on the things below. There was a lot of advice for other things that looked even more flight perfect (Lo and Sons) but were too pricey when I'm not a frequent traveler at all. These items were great for me and have the advantage of use outside of travel. My recent flight went perfectly!
I was able to get the Longchamps in dark purple and it holds as much as I need while having next to no weight itself. The bag is the perfect medium size, able to hold the wallet, my phone, keys, sunglasses and a few other small things. It's not enough for daily use for me, but I can still see getting a lot of occasion use from it. And the wallet is so thin and well designed I may switch to it for daily use at some point.
Going through boarding, the bag fits right inside the tote along with water, some snacks, kindle, iPad and glasses. Between flights it can come out for me to walk around while I leave the tote behind with DH, and is a good enough size for trips. For me, these were all really great purchases.
Thanks for your help, YLF community!