The context of the following conversation is The temperature was going to drop in the evening so, Skylar wore pants.:
Skylar says I was wearing shorts earlier but I decided to change..
The friend responds Why?  Your outfit looked really good..
Skylar responds Thanks, but the temperature is going to drop tonight..
The friend responds Maybe I should have worn pants too..
Skylar responds Well, I'm always cold so maybe you'll be okay..
The friend responds You're probably right..