I love this on you. I think the scarf pairing was brilliant, both because of the interesting texture/ pattern mix in itself and also because you love that scarf and it is so much "you" so you are bound to feel happier stretching out of your comfort zone for the other item (the plaid).
I also love your idea of a silk top and I, like others, for an alternative styling would probably "femme" it up a bit (as you already did with makeup and. your gorgeous hair etc.).
A skirt or dress, as Jenn said, or some other feminine elements seem key to making that type of large check feel okay on me. I used to own a 2 piece dress in fact, in this type of check, that I loved -- and I also had a buffalo check fuzzy/ sherpa type jacket in the 90s that I adored but it did take careful styling to feel good.
It's too bad about the jeans, but WOW do you suit a kick flare. Seriously, it's such a great style on you and I am forever jealous because it's just plain awful on me.