I did around the edges first being careful not to get any paint on the brass pieces or trim.
It took at least 3 coats to cover it decently.
Next I drew on some lines, very lightly in pencil, and painted them black to resemble zebra stripes.
Then I printed out some letter graphics, colored the back of them with a piece of chalk, and laid them out on the trunk using a framing square to make sure they were straight.
After taping them in place I traced around the letters with a pen. This left the chalk outline of the letters on my trunk.
Then I painted inside my chalk lines with some red paint, and yes, it took more than one coat.
Next I started sanding. I used a 150 / Medium grit sandpaper. Once upon a time I used a 80 grit coarse sandpaper thinking it would be much faster; and it was. In no time flat I had a trunk that was all scratched to hell instead of looking gently worn.
In this picture the left side only has been sanded so you can see the difference between that and new paint.
Then I mixed a little brown paint in a quarter cup of water and painted all over the trunk to antique it.
This is not the best picture, but you get an idea what it is starting to look like.
The next step was to print out some vintage hotel labels and coffee stain them. You can see this step in a previous post here.