Would it change the meaning of a sentence if I say "with" instead of "in" here?

Native speaker’s answer
Rebecca
Yes, it would change the meaning a bit! Since she would be inside the dress, they use "in". The use of "with" would imply that she is either holding it or next to it. "With" would be appropriate with bags and items she could hold, or even when referring to makeup. Ex: You look beautiful with that makeup on you! Ex: You should get that shirt. You'll look great in it. Ex: John looked great in his suit and tie that night. Ex: You'll look great with that bag.