@Drew_Long - you can do it without using psuedo-classes (which you can’t access in Webflow without custom css) or your second solution should work as well, just positioning an image or css shape within a parent. It depends on how you want it to look, if hand-drawn is a requirement, you may want to make a vector in Figma/Illustrator and use that, but you can also make the shape using css alone, which can be more flexible / lighter weight.
Here are a few examples: