I have the 31 size in Chalk. I had no trouble keeping it clean until I got caught in a torrential downpour in NYC. I kept my purse dry, but my legs were damp. I didn't want to put my Rogue on the floor at the theatre, so I rested it on my lap as I usually do.
I highly recommend that you do NOT leave a Chalk Rogue on moderately wet jeans for a couple of hours. Even ones that I have washed multiple times.
I noticed afterwards that I had a lot of colour transfer and dragged my husband to an after hours drugstore so I could find alcohol free baby wipes. They didn't help much. I ran to
Coach House the next day in a panic, and they told me to leave it with them for an hour and come back.
I did, and they removed 95% of the transfer. There's the faintest of shadows but I only see it because I know it's there. No one else would. Other than that, I wore it probably 50% of the summer, commuted with it, stuffed it in an office drawer, rested it on the floors (only in my own home)...and there are no stains or discolorations at all.
I didn't Apple Rain Guard it, because I can't get that in Canada. I haven't done anything to it really, other than clean and condition it before putting it away for the fall/winter.
Your bag will be fine. I just bought the Chalk Tea Rose Dinky. I think there's even less reason to worry with the flowers; I don't think they'd show faint stains as much as a solid block of leather.