For me, this is pretty much what I go through! (Unless I really really love it and fall head-over-heels and just need to buy it right that second-- but thankfully this doesn't happen too much!) 
I really try to think about the buying of a new bag properly / logically (honestly no handbag over $20 is logical but... can't resist, haha!), and would love to hear things you consider before going through with a new purchase! After all, money is money, and we always strive to make good purchases.

- What do I love about the bag and what purpose will it serve?
Sometimes I simply fall in love with how it looks, but I have to consider balancing it out with my lifestyle. How many similar bags to this do I have, and what does this particular one offer to my collection? If I add this to my collection, will I have to let another bag go? - Research! The size, the material / type of leather, wear-and-tear, strap length for my body frame...
I watch a lot of youtube reviews and unboxings, they're very helpful. - How long will I be keeping this bag and what's the resale value? What's the cost per wear?
I ask this to myself not because I'm terribly fussed about the resale value, but because of two things. (1) If I'm able to find this bag excellent condition or brand new on the preloved market for significantly less than retail, then why not go with the savings? Ex. I just bought an excellent condition Chanel Classic Flap for half of retail (2) If the bag doesn't work out for me, it's helpful to be aware of the resale value beforehand. - Compile the pros and cons. Do the cons outweigh the pros? If yes, do I still want the bag, and am I willing to compromise for all the cons?
- Do I still want it? If I do, do I have the budget? If not... time to save!
I really try to think about the buying of a new bag properly / logically (honestly no handbag over $20 is logical but... can't resist, haha!), and would love to hear things you consider before going through with a new purchase! After all, money is money, and we always strive to make good purchases.

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