My deal breakers that I've thrown out the window recently:
cross body only
medium size - so I'm not tempted to carry everything in one bag
patent leather - always thought it looked cheap and cracked eventually with wear
single compartment
gold hardware
zip top only
I also used to stick to neutral colors, but Vera Bradley cured me of that before I ventured back into
Coach last summer.
They were all violated by one collection - the Madison series in Vermillion textured patent leather. I like the light brass hardware better than traditional brass or antiqued brass, and I have always loved red and orange. The Vermillion is the perfect blend.
My current favorite bag - the Kimberley in Vermillion Patent, violates every rule on that list - 4 compartments, only one of which zippers, no cross body strap (and when you add one from another bag it is very lopsided).
But it's been by go-to bag for the last two months.
The patent cleans up perfectly - a quick wipe removes the salt and sludge that get on it in winter, the light brass hardware is classy, the middle pocket is perfect for my iPad, and I can slip a file folder or two so I can skip carrying a work bag some days. I'll love it even more when I don't have to wear a bulky coat - without the coat it works on the shoulder. And it has the perfect balance between structure and slouchy.
I also bought the small Madeline from this collection, but it's a touch too small to hold my planner, but I'm waffling on selling it because I love the Kimberly so much.
My only complaint is the hardware is light brass, but the zipper is full brass. But I'm probably the only one crazy enough to notice.
I'm still not a fan of:
true brass, antique brass
flaps
dark linings
suede
noisy hardware
rolled handles
super slouchy
super stiff-structured