All this talk of travel bags has me thinking about my needs. Great topic!
I like the idea of a weekender duffle and have a Louis Vuitton Keepall 55 to meet that need. Full disclosure, I also have a rolling carry-on suitcase and a lululemon duffle-style bag that work for this need; the type of trip typically dictates the bag I take. If there’s even the possibility I might have to check the bag (e.g., on a flight), then I won’t take the LV. Because airlines.
For what I would term my personal item (to use airline lingo), which is almost like a small carry-on to me, I like a sturdy, open tote. This bag can also double as a large day bag, or shopping tote, if needed. I have the LV Damier Ebene Neverfull in both the MM and GM sizes to meet this need; the length and type of trip determines which size I take. Full disclosure, I also have the Neverfull in Monogram Canvas (MM size) and the Goyard St. Louis in PM size, but those are work totes. And I have a Longchamp Le Pliage about the size of the GM. I have taken the Goyard as a carry-on in the past, but reviews have me concerned about wear and tear due to weight, while the Neverfull claims to carry more than I weigh without breaking, so Neverfull it is.
If I don’t need to carry much, then I like my Dior Diorama Croisiere Chain Wallet. It holds my phone; ID, credit cards and hotel room key; cash; a couple of tissues; lip gloss; and maybe a few other very slim items. It also has a detachable chain, so I can dress it up, or dress it down. However, it won’t hold sunglasses, guide books, or other bulkier items I might want/need for sightseeing. (I’m not a sunglasses-on-top-of-my-head person and hate to carry too many things separately.) Which leads me to…
A fourth category, which I’m not sure how to label. A roomier, lightweight day bag that will hold things like sunglasses (either in a drawstring bag, or the Valextra slim case
@880 ”talked me into”

), a guidebook, venue tickets, etc. I don’t need it to hold a water bottle and I rarely carry an umbrella, but I do sometimes need more room and find that the Venn diagram for what meets this category doesn’t overlap enough with the category in the paragraph above. As such, I find I need an extra bag to fit this need. I might not need it for all trips, but I do need it for some. I like my old school LV Odeon PM for this since it has an outer pocket that is roomy enough for many travel guides.
I will say that, with every trip to a new destination, I find myself on the hunt for a new bag that fits into my fourth category. It’s not need; I am confident something in my existing closet will work. It’s probably a combination of my excitement over the upcoming travel and my love for bags and shopping that gives me a reason to look. Sometimes I give in, sometimes I talk myself out of it, but it happens every single time.