You can only keep 3 bags.

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Ferragamo small brown handbag
Kooba Scarlett in army metallic
Ferragamo black handbag

Oh, and I need my Botkier stirrup. And my Coach patchwork. And at least one of my raffia purses for summer. Hmmm, can't throw away the Fendi baguette. Oh, heck, I give up.
 
This is actually quite easy.

LV Babylone. Functional and gorgeous at the same time. The brown go-with-anything bag.

Le Sport Sac Lulu minibag with the fruit design. Gracious, the number of compliments I get on that sucker is astounding. Totally casual.

Sigrid Olsen drawstring tote in black. Great leather, fabulous price, can be dressed up or down, and it will hold a ton.
 
Lambertson Truex Black Kansas Westport
Bottega Veneta Marco Polo Shoulder Bag
Kate Spade Black Leather Tote (sentimental value)

That would mean my Trigger and brand new Sienna would have to go but the first three have "seniority" as well as memories