Is this a safe space where I can admit how many of these I own?
It's 6. Five leather and one canvas.
Why? Because I carry this bag almost every day and I just kept buying it in different colors so it would match different outfits. In fact, the only expected color I don't have it in is the black because it feels more casual than my work outfits in black - I'm not certain why.
This bag fits everything. Rent the Runway return? Check. All my gym paraphernalia? Check. Packed lunch from home plus RTR return plus gym stuff? Check, check, check. It's always my "purse" carry-on for flights because if, for example, I'm using my backpack to cart photo equipment, I can actually stuff enough clothing in this for a week someplace warm.
And have I mentioned it's a leather bag for well under $200?
I'm not a huge bag person (but I'm starting to change that), and this goes with work, goes with play, goes with travel, and is inexpensive enough that I have 6.