When I'm not sure what to wear with an item like this, sometimes I will make a concerted effort to pop it on over any and all outfits/tops... even if my initial reaction is a most decided "no"... i.e., just play in your closet and try it over everything. Have fun and BREAK all the rules - deliberately - and something might just stick!
I would view this jacket as a great neutral that can go with virtually anything. I'd forget about matching the black. Come up with the clothes and then bring in a touch of black somewhere in the accessories - shoes or bag.
My first impulse would be to wear it with a blush pink top (something matching your lipstick shade), jeans (white or blue), cognac handbag, and then for fun I'd go with animal print shoes - cow or giraffe would be just perfect, tying in the cognac AND the black venting.
Faded boyfriend jeans would be delightful - the bigger and baggier and ragged the better, to juxtapose the polished tailoring on top.
Red would look amazing. A red bag. Or a red dress.
I'd also try popping this over a faded chambray or denim shirt.
I think I'd prefer to see this jacket with a solid top rather than patterned, and bring the pattern in with your shoes or bag.
I love the suggestion of a graphic tee. How do you feel about wide-legged pants - full length or culottes?