D.I.Y Dip-Dye Tropical Denim Shorts

I know the quality of this picture is terrible but forgive me, I made it in about a minute.
It's the plan of some denim shorts I'm going to make, I'm planning on dip dyeing, bleaching and studding a lot of pairs. I went scouring the charity shops yesterday for vintage high waisted jeans to make into interesting shorts. I find old jeans sit at a much better place on your waist and the denim feels nice and sturdy.

I'm going to buy pink and orange fabric dye and dip-dye the shorts, and then print tropical pictures onto iron-on transfer paper and iron it onto the back pockets.
What do you think, do you reckon it will work? When I get it done I'll post pictures..if it's successful!