I found all sorts of threads of people trying to space out the categories in the side box...but not quite what I'm looking for.

What I'd like to do is have a layout like this:

Shop by Category
Shop by Occasion
Shop by Gemstone

Rings (Ring Size Chart)
Earrings
Brooches & Pins

Chains & Bracelets
Necklaces & Pendants
Matching Sets
Birthstone Chart

Not necessarily where those gaps are, but the ability to have a gap between certain items to break up the list and create sections.