Ok, I can't totally narrow it down, but my top 5 are in the first photo except I changed my mind later and I put my amended item photos below... and then I'll discuss bag "family" faves
as well.
First the group shot of my initial top 5 LOL (top row then bottom)
1) Musette and the bags in that family (Swag, Carrier, Pony Express) are truly my LOVES.
2) My favorite bag in the Berkeley family , reverse suede, is the Field Bag (I have a drawstring bag coming so who knows where that will fit in the fave list LOL)
3) My go to bags have been and always will be the Willis Family (including the City bag pic'd) I have several of each style/color that I switch into. Still looking for a red.
4) I have the Beaumont pic'd here, I love her, but realized later I probably would have placed the Sheridan Sheffield Bucket in that spot if I were to do a re-shoot. tough choice. Sheridan is below
5) I have the Stewardess pic'd and I own 4 of these and I think it is a TRUE MUST HAVE CLASSIC. However it's a tie -in my heart- with Bonnie Skinny Tote below which was made technically POST Bonnie but I wasn't sure if I should put the slim tote in this group so I didn't.
So, here's Sheffield Bucket which is my all weather go to favorite:
And here's the Bonnie Skinny Tote which I adore !!
Just for your photo reference I'll also show you a bag I love from the Madison Line which is one of the larger bags made by Madison since most of those bags were just too small for me tho' I love that leather!!
Sorry, I kind of cheated. but I don't think I have just 5 faves. I could have added even more to this easily