What's your most tried-and-true comfortable bag?

I'd have to go with my Tylie Malibu Apache flower in chocolate pebbled leather. It's so light, the leather is super soft and it holds a ton while being very comfortable on the shoulder.
 
I have to say my Lockheart Brady Bunch, multiple inside pockets, the soft leather, the color.

I still catch my breathe when I look at her. She receives compliments everywhere I go and is such a work horse. She can stand being thrown in the car after a heavy down pour, you name it she can handle it. I just saw one on ebay and I swear I want to buy her again for that just incase something happens to her.

tried and true, the No. 1 love of my handbags
 
My Balenciagas and Anna Corinna bags are the most comfortable.

My Bal Day is easiest to sling on my shoulder, but the City is smooshy and has the handheld option as well as the shoulder strap.

I have 2 Anna Corinna Mini City Totes because they are so versatile to carry.
 
I tend to carry clutches, whenever possible and they are all comfortable (although, none of them are vastly oversized, because I find very oversized clutches to be too heavy and unwieldy); but my most comfortable shoulderbag ever is, without question, my Chloe Tiger Hobo.

It is the perfect size and shape, is soft and squishy and so molds to the body perfectly, has a long, wide, self-tie shoulderstrap (which can easily be worn cross-body, if desired; although I don't tend to) and is light as air (mainly due to the fact that it doesn't have any extraneous HW [just two zips, one inside and one outside]).

I really wish Chloe still did their self-tie hobos, as they were simple, but perfect. :heart: :heart: :heart: