I have a LV Speedy and whilst it is a useful bag in terms of design (I have the bandolier, the crossbody - and it's a big size), I live rurally and so it doesn't get much of an airing.
Pre-Covid I'd use it going around town but tbh you just don't see them in my rather sleepy city so I was always a bit aware of it. Though the crossbody strap does make it look more casual. But I simply don't live in a part of the world where people wear this sort of stuff.
Post-Covid I haven't used it at all. I haven't gone anywhere! I'm invited to a party soon but it's an informal thing so would it look knobby to bring a LV Speedy when people there will have bags from River Island? Probably! 
It's my all time favourite bag, but I freely admit it doesn't work for my lifestyle currently. But these expensive bags are meant to be lifelong essentially - so we hope that as our lives progress, our opportunities for wearing them will evolve.
Or maybe I'll give less of a shit!
I actually sometimes think a Chanel would be more camouflaged. Especially the ones without the 2 Cs at the front - I believe they're called the Reissue model? But then again I don't want to get a Chanel for everyone to just think it's from River Island!!!
My all time Chanel fantasy is the Business Affinity bag and if I won the Lotto tomorrow, I'd fucking buy it and just wait for the right opportunity to wear it.
And in the meantime just admire it in my wardrobe, like I do with my Speedy!