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I think it might be a good idea to put that money aside until you see a bag you MUST have. Just because you have $X to spend, that doesn't mean you have to spend $X. You might find something you love for a fraction of that cost. If you don't see anything that gets you excited, just wait until you do. Buy something you LOVE, and that you can see yourself using on a regular basis. For me, that wouldn't be Chanel... but everyone's lifestyle is different. Enjoy the search & post back when you decide on something!
Big contender is also the 36 cm Hermes Garden Party. The SA will give me a call and send over pics when the bag is in stock in my preferred colour.
I'd second this. It could be designer or else. Wait until the rush of excitement die down a bit and see what's out there and you really really love. It's easy to buy once you have the fund ready, but so hard to get rid of it once you fall out of love.
I love the Hermes GP (have three of them!), but one caveat is that they can be difficult to fit over your shoulder if you have a bulky coat on. I noticed in most of your pics you're looking at shoulder bags, and the GP was not really designed with this in mind. I carry mine over my shoulder, especially now with warmer weather, but pretty much gave up on the bag last winter in favor of a simple Longchamp Le Pliage. Just wanted to be sure you have this in mind when considering this bag.
Very true!
The Hermes is beautiful, good size for everyday too, same for the Gucci, but that's a bit flashier with the logo. The Woc is practical for errands and shopping and such, but not for everyday imo, unless you don't carry much. Do you want completely understated or something a bit more obviously "designer"?