A "clout-shoe" is a country bumpkin, and "clout" was the old word for a piece of cloth ("Cast ne'er a clout 'til may be out" we do say in the West Country). Perhaps if you couldn't afford leather boots, you had to make do with cloth.

The phrase "to clout a shoe" also occurs in "The Yeoman's Wooing" :-

I am my father's eldest son, my mother eke does love me well / for I can bravely clout my shoon and I full well can ring a bell.

I have always assumed it meant he could look after himself, which sort of agrees with Crane Drivers post of 22nd, if Henry 8th is in fact the Man in the Moon. Our Henry was certainly a strong supporter of the Pope before they had something of a disagreement. In 1521 he got the special title of Defender of the Faith for writing an essay attacking Luther.

On the other hand, in Eric Partridge's Dictionary of Historical Slang a man in the moon is a fool.