"Io ho un serpente nello stivale."
Translation:I have a snake in my boot.
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but that doesn't answer why it would not be "ON the boot" compared to "IN the boot" because you can have things on your shoes that are not inside your shoes. Sometimes I have mud or a bug ON my shoes but not IN my shoes (thank god). Semantically, could both IN and ON have been correct in this boot case? If not, how would you say "I have a snake ON my boot" ?
two good and easy charts for prepositions
Partly because "nello" means "in the" and not just "in". So you at least need the "the" to make a coherent English sentence. But as a previous commentor said, the "my" is implied because Italian doesn't use possessives for clothing unless you're specifying whose item it is. If there is no possessive it is accepted that you're talking about your own item.
The difference between and nello and nel is the same as la/il and lo. Use the one that ends in o for words that start with s+consonant and z+consonant. Il piatto would be nel piatto. Lo zucchero would be nello zucchero. Etc. It took me a little bit to realize that as well because it isn't very well explained, but if you know which "the" to use then you'll also know which "in the" and "on the" to use.
These are called "prepositional articles" because they combine a preposition and and article together. There is a nice chart showing the different forms at http://italian.about.com/library/fare/blfare153a.htm