echo "${PATH//:/\\n}" | awk '{print length, $0}' | sort -n | cut -f2- -d' '
For example given PATH=/usr/bin:/bin, it would print:
/bin
/usr/bin
echo "${PATH//:/\\n}" replaces the : separator in $PATH with a newline, so that we have one path per line| awk '{print length, $0}' prints for each line in the input the length of the line and the line itself, separated by a space| sort -n sorts the input numerically (instead of the default: alphabetically)| cut -f2- -d' ' prints the second and all following fields of the input (-f2-), delimited by a space (-d' ')