~What Is Your Most Used & Most Loved Bag~??

My Pochette Metis in empreinte noir.

It's the perfect size for all my everyday items, and it doesn't stick out too far when I wear it crossbody.

I love the top handle for grabbing it out of my passenger seat and for pulling it off my shoulders when I take it off.

The back pocket is perfect for my phone.

I like the unique clasp to open and close it.

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My Fendi Fendista. It’s just so easy. Performs the same functions as a WOC, but with a slightly larger capacity. It’s a little slouchy, but still has enough structure to be a flap bag. And it’s a great day-to-night bag: perfect for errand-running and works a treat as a clutch for dinner dates in a pinch.

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My most used bag by Miles is my Jimmy Choo navy matte crocodile bag, bought new, years ago(can’t remember how many, before I moved to where I’m living now, which was 2018).
I used it 365/365 whatever the weather, rain or shine to the exclusion of my other bags for years-the only reason I use my other bags really is an irrational fear that it’ll wear out..
I have 8 bags in total, want another 3, all exotic, far more costly than the Choo, but when the Choo wears out I’ll be heartbroken ..
Definitely great CPW

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I'm with @sdkitty here, I switch bags nearly every day. Some everyday life favorites include LC LP Chocolate LLH, MSH and flap bag, Coach Field tote 30, Littlephant hobo in Tiger Island print, DKNY black leather hobo and my 2 Day Et Gweneth Work totes. I also love my Kipling bag for rainy weather or for days I have to walk alot as they are lightweight and durable (and also, as they are sale finds, inexpensive).
 
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I'm with @sdkitty here, I switch bags nearly every day. Some everyday life favorites include LC LP Chocolate LLH, MSH and flap bag, Coach Field tote 30, Littlephant hobo in Tiger Island print, DKNY black leather hobo and my 2 Day Et Gweneth Work totes. I also love my Kipling bag for rainy weather or for days I have to walk alot as they are lightweight and durable (and also, as they are sale finds, inexpensive).
sometimes you're going to be buying or carrying stuff so you want a large bag. other times you're going to be wearing bag on shoulder for a long time so you want one that's not too heavy. and as you said there are bags that are better on a rainy day.