How to sort numbers according to the first digit?

1, 1, 2, 2, 10, 10, 22, 23, 100

Interesting, but it's the way files are sorted

just, in this particular case, you need to remove from name all what is not a number:
dir c:\\test\\pstest | sort {[int]($_.name-replace "\\..*")}

the same result will be if you change the regular season like this:
dir c:\\test\\pstest | sort {[int]($_.name-replace "\\D")}

when you change the file naming scheme, the regular season, too, will need to change.

and to sort in reverse order sort-object is the key-descending. just add it to the end of the row.

Obviously, it is not necessary to call files of sorts in numeric order only explorer on Windows. Fill the number with zeros.