For both work and play, I often come back to a lovely vintage Bosca tote that looks very much like the current "Old World Tote" (stock photo below from the Bosca catalog). Mine was made with a rich burgundy interior for the original owner (a family member).
I choose a few bags to have in rotation per season and I use whichever works with the day's outfit and weather. They are standing in order and in dust-bags on top of my piano
Right now (AW-15/16) my most used bags are:
BV Gunmetal woven Cervo Hobo
Hermes Bambou (green) all-leather GP Gucci Aviation Blue Large New Bamboo Top-handle
Liberty Black leather Iolanthe-embossed Briefcase
Cambridge metallic silver 11" satchel
I can't even imagine wearing the same bag every day because I change my bags daily to accent my clothes so I don't really have one go to bag. Also, my bag use is seasonal. This past year my top three have been:
Fall15/Winter16
Proenza Schouler Small Courier in black leather w/both SHW & GHW
Chanel Jumbo Classic Flap in Black Patent w/ SHW
Jimmy Choo Metallic Leather Biker Bag
I am doing some personal research for bags that are used most frequently. I would love to know what your most-used (NOT your favorite in your collection, just most-used!) handbag is and, if no photo, what color it is. Why it is your most-used would be fun too.