Best timeless casual designer shoulder bag?

The leather versions of the Gucci Jackie 1961 and Prada Cleo are very classic and fit your needs (shoulder bag and good capacity). Both are open top bags though, so I'd be concerned items could fall out.

I think a timeless bag is one that matches the outfits you wear the most, and is practical for your lifestyle. For me, it's the Loewe Small Puzzle and Celine Classic Box Bag :biggrin:
 
For a mid-priced, contemporary option that gives a similar (if less branded) feel to the Jackie and Cleo, it may be worth checking out the reissued Coach Ergo. That might scratch a similar itch at a fraction of the cost, and the natural leather or glove tanned leather are likely to last well. If you remove the detachable tab, it’s entirely unbranded from the outside, so less likely to feel dated.

I’ve personally been eyeing one for myself because I love the feel of the Gucci Jackie, Prada Cleo, and Hermès Trim but I’m not sure if that style will go out of trend again soon so I’m hesitant to purchase a higher end brand of that shape.
 
Just my advice. For a timeless bag, try to avoid:
  • adornments like studs (think Balenciaga Neo, avoid)
  • Avoid clasps, logos
  • stitching or visible cutout panels of leather (think Celine Luggage, avoid) - even the small panels where the handles attach can date a bag very fast (I'd say LV Alma risks this).
I'd steer clear of the Gucci Soho Disco - if it's the one with the GG embossed in the leather, these styles are remixed regularly and they can look old fast.

The Prada Saffiano Tote bag is a good choice. Also Prada Cleo is classic.

I'll have a think about this, but at this time, my first thought as to a new suggestion for you is the Celine Belt Bag. For me, this is just about perfect. The face is clean and simple, it has no visible metal parts, no clasps all the panels are purposeful and clean. It's been around since about 2015 and Hedi Slimane (new designer at Celine) kept it on with good reason. A timeless bag. Clearly an homage to an Hermes Kelly bag which is a legendary classic.

Celine Belt Bag.png
 
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Maybe consider Issey Miyake bao bao in tote or crossbody, it is more on the low - mid range and if you want it for everyday, it's perfect, doesn't get any damage and holds a lot! Also, maybe it's not an IT bag, but it has been around for some time and it's not going anywhere :smile:
 
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I have these 2, LV epi leather trocadero, very hardy and great for everyday trips to shops, or anything casual. Being older styles there are better priced, for me they were in the AU$300 range. I think anything leather by LV is a better choice as its not getting that dirty handles look to it. They do have issues with sticky inside pockets resulting in flakey leather, but i actually dont care that much about it.
 

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