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English is not my native language so I have gone through the pain of learning the difference between in, on, and at. However, it is common in the U.S. to refer to someone wearing a hat as X in the hat. A notable example is the children's book The Cat in the Hat by Dr. Seuss.

Using the latter example, we know that the cat is not inside the hat but instead the hat is on top of the cat. Why is it acceptable to say The Cat in the Hat?

Why is the expression X in the Hat acceptable?

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Wearing a piece of clothes can be expressed like this:

He looked good in his trench coat.

They debated about running bare or in shoes.

So it does not really matter whether the whole body or just small parts of it are actually "in" the piece of clothing. Therefore it seems perfectly valid to say

Cat in the Hat.

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Yep. You can be in a hat, in your shoes, and even (depending on whom you ask) in earmuffs, in a scarf, in makeup, or even in sunglasses. It's one of the stranger uses of "in", perhaps, but at least in certain dialects it's remarkably consistent. – Jon Purdy Oct 29 '10 at 22:06
to me, it helps to mentally say "You look good in that makeup" to make it sound normal. hearing it more abstractly, like "Being in makeup makes me feel better" still sounds strange. – Claudiu Oct 29 '10 at 22:12

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