In the past, my go-to tote for carry on is the Longchamp Le Pliage (not luxury, but just so lightweight and versatile). We are going on our first post-COVID trip in a couple weeks (!!!) and I'll be trying out my recently acquired, first ever Neverfull (Black Empreinte) in place of the LP. Hopefully the lack of a zipper doesn't cause issues for me.
For actual bags to use, it varies depending on the destination, but I usually pack my Chanel Reissue (understated) and a WOC (which I use as a wallet in my tote). Both can be worn cross body and dressed up or down. I generally use a Chanel WOC for concerts or sporting events that allow small bags in general and I have a an ecco cross body bag that is within the NFL's strict bag size limits. But reading the bag restrictions these days is key...I've seen some events with "No Bag" policies lately, so be sure to check. Have fun!