Do greyish colored plaid shorts and a brown t-shirt match?

Answer 1

Nope, not unless there is brown in the plaid.
1] black goes with almost everything except brown
2] gray goes with everything except brown
3] brown can go with everything except black or gray.

Answer 2

No!!! Black and Brown can go together but not Gray and Brown, try a Black or White t-shirt instead.

Answer 3

yeah

Answer 4

not particualy