In the case of shoes, it means wearing them a few times in order to make them feel less like stiff new shoes and, therefore, more comfortable. I've never heard of anyone breaking in a dress.

English Teacher
Hello.
Does "break in" mean to use something for the first time? Or does it mean to use something for the first time to make it comfortable?
Have I used it correctly?
I broke in that dress at the wedding of my friend.
I broke in the shoes at a friend's party.
In the case of shoes, it means wearing them a few times in order to make them feel less like stiff new shoes and, therefore, more comfortable. I've never heard of anyone breaking in a dress.
Remember - if you don't use correct capitalisation, punctuation and spacing, anything you write will be incorrect.
I see. Is there an idiom which means to use a dress for the first time?
You could borrow from other contexts and say something like "I premiered my new dress at ..." or "My new dress debuted at ...".
Remember - if you don't use correct capitalisation, punctuation and spacing, anything you write will be incorrect.