For me, some things can stand out and some can be supporting acts. Because I rarely pattern match, and almost always wear a medium size print somewhere, my bags are usually more of a support. So while I am drawn to a fabulous big print on a summer bag, floral or graphic, my purses read neutral.
Maybe next summer I'll add a neutral capsule and a big print bag. Something to look forward to.
Rachy, it sounds like you didn't like how the plaid bag looked on you. I wouldn't buy it then. But maybe I'd keep an open mind to seeing a similar one in better shades of black and white, or different colors.
I do sometimes wear things I like that I don't think look that good on me, usually because they are dated. I wear them in three locations-at home, on a quick walk (we never run into anyone and usually I have a third layer on anyway), or on a long car trip when I want to be cozy in the car.