with / in
why do we say "you look good with short hair" but "you look good in jeans"?
Re: with / in
You use "in" for items of clothing, because a part of your body is literally inside the clothing. For accessories, jewellery and parts of the body (hair is a part of the body), you use "with".
Some things like hats and shoes are sort of on the borderline. Shoes, for example, are accessories, but your feet do actually go inside them. You can probably use either "with" or "in", as you see fit.
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