I change my bag almost every day. Sometimes I wear a bag for three days, but usually not more than that, even if it is a favorite. I tend to safe favorites for special occasions a bit too much

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Mostly I create the outfit first and then add the bag that works best with it. I want the color of my outfit to go well with the bag color.
At the same time I try to pick a bag that I haven't worn recently. So even though my black bags go with a lot, I will avoid picking them over and over again.
Sometimes I also create an outfit for the bag. What helps me visualize any outfit is holding a bag close to the fabric. I basically take a walk past my clothing rack and closet (which is very colorful and diverse so I have to do this).
EX: I have this taupe and brown, preloved Fossil bag I recently got on Ebay and I felt it would go great with khaki, brown and beige for a day at a animal park with the family.
The bag also fit the occasion because I don't worry about it getting dirty.
So I guess I pick by:
- Outfit and Colors
- Occasion
- Bag I want to wear
I also chose bags the day before.
I do this subconsciously, so it was hard to put it in words. Hope it makes sense.

I feel like all my bags are getting enough action. Plus trying to find a great outfit for a bag that isn't my favorite can actually help me appreciate the bag more if it matches well. The yellow bag in my siggie is H&M and not a favorite, but it looks super cute whenever I want a pop of yellow or pair it with soft yellow colors.