Hey, good to have a bit more info about you and your look etc and how you’ll likely use a bag. I think the Louis Vuitton is slightly less high maintenance than the others, and the strap handle would be more robust and comfy than the chains, as
@A bottle of Red said. But the Louis Vuitton is not so strong in the night transition, which is its main weakness. The others are a bit more night, but the Bulgari could be a bit delicate and the Saint Laurent with that tassle, also potential for it to get damaged. Quite exciting to think about what bag you could get actually! (as I can’t afford one!), so I have come up with a some suggestions:
View attachment 5040847Gucci Bamboo, £2600. Classic, timeless, "friendly" bag, a Gucci look through the ages, saffiano very tough, But very pricey, possibly a bit old-fashioned for your look, might not be edgy enough.
View attachment 5040896View attachment 5040900Prada Cahier, £2200. Lovely and a statement, looks industructable. Timeless class. Chain, but with leather shoulder part. Will do the day and the night. However, definitely quite bling and could attract attention. A little pricey, but it's clearly had a lot of work put into it.
View attachment 5040852Loewe Puzzle Medium, £1400. Really interesting shape to me, all about the pattern and for someone who will look twice and appreciate it on its details. Practical and robust, nothing likely to get damaged. Possibly could be considered chunky and almost like a book bag, but I think it will transition to night, depends how it's styled - when you mention motorbike boots, for some reason I feel like this has good matching potential, there's something a bit like motorbike gear in those panels with the black glazing. I think this would work with a black leather jacket really nicely.
View attachment 5040855View attachment 5040858Marni Trunk Medium, £1450. Really like this, quite soft and feminine design, saffiano again, so very tough, and a bit of an outlier brand which I think is cool, won't see many of these around, bought by people who really dig in fashion. Plenty of room and compartments inside.
View attachment 5040853View attachment 5040854Balenciaga Small Hourglass python-effect, £1450. Stunning, edgy, but not over fussy for the day, amazing night time potential, actually practical I think, has some width to it and great side profile. The red/black will let it match well with a darker wardrobe, but also light-coloured items. Might be too edgy?
View attachment 5040950Balenciaga Small Hourglass in regular, £1450. Also! In glossed leather though.