I cant seem to figure out where I would start to make something like this:
I just want to have something to select pairs of text and icons like in windows explorer with "Small Icons" selected.
from tkinter import *
from tkinter import ttk
title = "Select Sheets Items"
dlg = Tk()
TkTreeCtrl - https://tktreectrl.sourceforge.net/ - can do stuff like this, e.g. https://tktreectrl.sourceforge.net/pics/explorer4.png . It does take some study to get into, but it's seriously powerful.
I've only used it from Tcl, but it appears you could use it from Python via https://tkintertreectrl.sourceforge.net/ .