Hi : )
I don’t think it’s possible with the selection tool, but you can achieve something like that with the shape tool.
Here’s a screenshot :
You can therefore choose between several shapes, from square to freeform. In the tool options, you can choose to have a fill, an outline or both.
Using the freehand path tool in raw mode (under pencil>precision in tool options) is quite similar to the lasso selection tool.
The size and texture of the outline are defined by the brush previously selected (here I used a kind of chalk pencil).
I hope this help : )