Naked Bob Dylan Robot has something to say about the meaning of "Leopard-Skin Pill-Box Hat."

As channeled by betamax3000:

Well, you look so pretty in it
Honey, can I jump on it sometime?

The Leopard-Skin Pill-Box Hat Represents the Stylish Repression of the Sexual Urges of the Hat-Wearing Woman -- the Hat is a "Pillbox", thus referencing both Birth Control and Containment --, and How those Urges Create a Corresponding Attraction in the Male, as the Leopard-Skin Pattern Stimulates Animal Urges. This Becomes More Obvious in the Following Lines, where the Titular Hat is Compared to A Mattress:

Yes, I just wanna see If it's really that expensive kind
You know it balances on your head
Just like a mattress balances
On a bottle of wine
Your brand new leopard-skin pill-box hat

That the Mattress is Balanced On a Bottle of Wine Implies that the Man is Contemplating the Use of Alcohol to Achieve the Goal of "jump(ing) on it sometime."

However, this Desire Remains Unrequited, as Evidenced in the Following lines:

Well, if you wanna see the sun rise Honey,
I know where We'll go out and see it sometime
We'll both just sit there and stare
Me with my belt Wrapped around my head
And you just sittin' there
In your brand new leopard-skin pill-box hat

Notice that they Will "Sit and Stare": there is No Jumping Upon the "Leopard-Skin Pill-Box Hat". Furthermore, The Man Now Has a Belt Wrapped Around His Head, Indicating Restraint of His Hat-Jumping Thoughts, and -- Possibly -- Implying a Restraint Around His Phallic Head. Meanwhile, the Woman is "just sittin' there" and there is no further mention of a Mattress.