Love the shirt and your styling, Suz. On the how to predict question:
Pattern: I think a piece is more versatile when it picks up more than one color (unless we intentionally want to cut ourselves in half, which some people can do!)
Color: I think it helps when the colors in the pattern are our staples, and we know we have several coordinating pieces (in your case, bottoms) that go with (in your case, navy and white)
Vertical Proportion: The shorter length is a clue for us short-legged gals that our vertical proportion will be right
Horizontal Proportion: Checks and strips on top are clues to help balance us curvy-bottomed gals
Fabric/cut: Not my expertise, except to say that I pick washable fabrics.
For dresses, I take notes from Penny, above: If it's a solid color, wide or V-neckline, sheath silhouette with tapered skirt or flare bottom that collapses back on the body--or straight shift (not flared)-- I know it's a good candidate.
My pieces that meet the above descriptions are MVPs!